This is a very long story.
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This is a very long story.
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Summer 2013, I turned 25 years old. I will not lie and say that I was thrilled or anything like that, to be honest with you, it was quite the opposite. I was not happy in the least bit to be just another year older, as I liked to say. Especially given the fact that at the midway point of my twenties, I still had been unable to find a woman that I could develop a meaningful relationship with.
I'd never, ever, had any real luck with women since I had first started dating when I was thirteen years old... I had been in one relationship after another. Some of them just went sour, some of them had no real chemistry, and then there were the few in which I had been cheated on... like my most recent one with a girl named Alisha.
Maybe, that was what had me so depressed in the first place... see, I had only found out about Alisha cheating on me just a few short days before my 25th birthday and we had been dating for a year. I liked to say that I had actually been in love with her, it was the first time in a long time that I had felt like I could trust a woman. Look where that got me.
So needless to say, I wasn't quite looking forward to spending my birthday alone. My parents, seeing as I was older now, were obviously not going to throw a party for me. They invited me to dinner, gave me a card and bought me a cake and that was really about all there was to that. My depression had sort of brought me down to a level where I had very few friends anymore, so there was not anyone I could spend it with just hanging out.
All I really had was work and then home to have dinner and maybe crack open a couple of beers. I guess a part of me was almost content with that.
Then, I got a text message from someone I had not spoken with in a little over a year... his name was Rob. Rob and I had been friends since we were ten years old in elementary school. He was the oldest friendship I had in my life, and we had always been in and out of contact with each other over the years but we always remained friends regardless.
Hearing from him after a year of not talking for no real reason, actually seemed to lighten my mood a bit. I smiled as I opened the message and it read, "Happy birthday dude! What are you up to tonight?"
"Thanks man. Probably nothing, not feeling up to anything big this year," I messaged back.
"Man, give me a call, let's talk." He must have been watching for messages as he returned mine almost immediately.
Sighing, I went into the phone book and clicked his name, dialing the number. After a couple brief rings, Rob answered the other end.
"Hey what's going on bro, it's been so long."
"Yeah, I know dude. What're you up to?" I asked.
"Not much man, listen, you staying in all night on your birthday?"
I hesitated, taking a swig of the beer I had in my hand and leaning my head back against the cushioned recliner.
"Yeah dude... I'm feeling pretty down."
"What's wrong?" He quietly asked.
"It's just... I don't know man. I'm sick of women, is all I suppose."
"Alisha broke up with you didn't she?"
He knew... he always seemed to know. After all, he had known me half of our lives, so I expected he would. Rob always had good luck with women, while I always had shit luck. He tried to help me out quite a few times. It was never his fault that it never worked, he tried, and it was all on me for some reason. I was the one who had apparently been cursed and that was not his fault.
"Yeah, I don't know what's wrong with me man."
"Nothing's wrong dude," he replied. "Listen... why don't we get together and have a few drinks tonight man? Beats staying home on-"
"I don't know dude," I interrupted him, "I'm not feeling up to it really."
"Oh c'mon Jay, don't beat yourself up like this. Tell you what... you really don't want to go anywhere? Let me come over there, I'll bring a couple six packs and we'll have a great time."
I saw no problem with that, what was the harm really? At least this way, I would not have to deal with people or the general public and I would be able to hang out with an old friend and maybe it would cheer me up.
"Yeah sure... come on over," I agreed.
"Great, I'll be there in about half an hour."
We hung up, and I pushed myself up out of the recliner and started tidying up the apartment a little while I waited for him to arrive. About an hour passed before I heard a loud knock at the apartment door, and I went to unlock and open the door. I pulled it open to see Rob standing there with two six packs as promised, and that same old lopsided grin he always had.
We gave each other a handshake and brief hug, before I led him into the apartment and shut the door behind us, then we both took a seat at the kitchen table. We ordered a pizza and split it along with the two six packs he brought with him, and we started catching up on missed time.
I told him about Alisha and how I caught her with her apparent ex-boyfriend. I told him how she had really felt no sort of remorse or anything like that...it really fucked me up, but he could see that clearly without me having to tell him. As we started to feel the effects of the alcohol, we swayed from what I viewed as depressing talk. When I would drink, I was usually more cheerful and I started wanting to talk about happier things the more I felt it kicking in.
I told him about the new job that I'd had for a few months now, and how it was really working out well. He asked about my family and how everyone was doing, and I went on to ask the same questions in return. Somewhere along the line though, I guess I started to feel down again, and naturally, he picked up on it right away.
"Hey man, listen... don't sweat that Alisha bitch okay? Seriously, the time I met her she came off as a total bitch."
"Hah, you only met her once Rob."
"Sometimes it only takes one time to know a bitch," he slurred and we both laughed.
"Well I appreciate it Rob, but to be honest...you've always been the lucky one when it comes to women, and I don't mean any offense, but I don't think you understand how it feels to be twenty five years old and have zero luck with women."
"Ah, come on, don't be like that. I know what you are saying, I do, but let me tell you something not a lot of people know. The last three years... I wasn't doing so hot with dating."
That was a shocker, I thought silently. Rob not doing well with women? That was something I never thought I would hear.
"Well... why not?" I asked.
"To be honest... I don't really know. I do know what you are feeling. I didn't say a word about this to anyone until now, but a few years back this one chick I was seeing hooked up with someone else behind my back. Really fucked me up in the long run too, but I don't know. After that I was just not the same, I started going out and hooking up randomly and drinking a bit more."
I had never known any of this, it must have happened during one of those periods where he and I had not been in contact all that much. Rob had always been pretty good at keeping things from people when he wanted to, the complete opposite of me, who was the kind of person that you could read easily.
"It's all good now though, you know why?"
"Why's that," I asked curiously.
"Because it made me realize something... women are evil. But you can't really live without them right?"
"That's the old saying, yeah," I said laughing.
"Yes, it is, but what if I told you I found a way around that? I found someone else man... I found someone I actually love, and hell, she's my best friend."
Holy shit, I thought to myself. Rob just admitted he had fallen in love with someone? Now that was definitely something I did not see coming.
"That's awesome dude! What's her name?"
"Her name is Annie. She's fucking hot as hell too dude. But I'll let you in on another secret here," he said slurring his words.
He was clearly a bit more drunk than I was, so I was not sure whether to take whatever he said next seriously or not, but I laughed and listened as he continued on.
"What if I told you," he slurred. "That there is a whole different breed of women out there... that can rock your fucking world, like it has never been rocked before. Annie is one of them, and I can tell you, she is living fucking proof. Man, I can introduce you to some people who will make you forget all about Alisha and all those other bitches faster than you can blink."
I was pretty sure it was the alcohol talking, I started laughing hysterically.
"No, no, dude I'm serious," he said laughing with me.
"Oh come on Rob, a girl is a girl right? You're not making much sense."
"No, listen man... here, look," he pulled out his cell phone. A few seconds later, he was showing me a picture of a beautiful blonde wearing a sexy blue dress.
He showed me another of the same girl, only in this one she had her arms around Rob from the back and her chin resting on his shoulder as he held up the phone to snap the photo.
"This is Annie," he said laughing, "Ain't she fucking gold man?"
"She's pretty cute," I replied honestly.
"Right," he looked at me earnestly, "now what if I told you, I met her somewhere that doesn't cater to your average women."
I was really having a hard time trying to figure out where he was going with all of this, but I laughed and listened on.
"I met Annie at a Transsexual club man, she's a tranny."
"No fucking way," I blurted out laughing at him.
Now I really was pretty sure it was just the alcohol talking. There was no way Annie was a transsexual. She looked hot as hell, much like he had described her, and I could not see any reason to believe she was actually a man. He had to be fucking around with me or some shit.
"I'm serious!"
"No you're fucking not, quit joking."
"No, really, here look," he handed me the phone again and my eyes went wide. The next photo he showed me was one of Annie lying sprawled out across his bed, completely naked, legs spread wide apart... and to my surprise, standing straight up from where there should have been a pussy, was a huge, throbbing cock.
It had to be at least eight inches long and it was completely erect and holy shit I was in a state of shock. I had to take a very long swig of my beer before I could clear my head enough to say anything after that. Rob was waiting for me to speak, a huge lopsided grin on his face and he looked like he was ready to laugh at me and my reaction.
"Dude... what the fuck,"
That was the only thing I could bring myself to actually say at this point... what the fuck. Rob was definitely not gay, he had never once given me reason to believe while we were growing up that he was gay. And yet here he was telling me about this hot ass girl he was fucking and then showing me a picture of her and I find out she has a dick. What sense did any of this make? Zero in my opinion, but I believed him now
"Holy shit... that's real? Like you didn't Photoshop it or anything?"
"No, it's completely real, she's a real transsexual."
"Wow... I mean... are you gay?"
"Fuck no," he laughed. "Look at her dude, that's not a man right? She looks like a woman, acts like a woman, smells like a woman, she even sounds like a woman. She gives better head then a woman though, and that's because she use to be a man and she knows what men like more than a genetic girl would know. She's all women she just happens to have something extra."
"That's... that's fucking crazy."
"I know right? And the best part? Anal sex all the time, do you know how many genetic girls I dated that were willing to have anal sex with me, only one. With a girl like Annie, anal sex is a fucking given."
He had me laughing again, and I finished off my last beer and stood, my legs shaking beneath me as the room spun just a little. I still had a lot of trouble taking all of this in though, and I had a LOT of questions to ask him.
"So like... do you like... do you always GIVE anal sex to her... or so like, do you take it from her too?"
"Hah, hah, nah man, that's not for me, some of the guys at the club like it but it's not my style.
Annie would be willing to do it if I were interested, but we never bother. But listen man, you should come check this place out with me."
"Nah, I'll pass," I replied staggering to the kitchen.
"Oh, come on, it'll be fun! You'll love it, I swear. I'm telling you, there is no women like a women with a cock Jay, you will love it I promise."
"I don't know... I mean... what if she wants to like... bend me over and stuff?"
Rob started laughing, quite loudly I might add, and I started with him. He stood up from the table, almost knocking over the chair and stumbling out behind me giving me a hard pat on the back.
"There's all sorts of them there... some like that stuff, some don't. But I mean even the ones who do like it, they aren't pushy about that. If you find a girl who wants it and you want it too, that's great, if you find a girl who wants it and you don't nine out of ten times they are pretty respectful. No one's going to make you do anything you don't want to do."
Maybe it was the beer, but I was actually considering checking this place out. I wasn't quite sure why, but for some reason I was interested. Maybe it was the fact that he had stressed how much better these women were at making a man feel good then genetic women. But then if he had only been with one of them, how could he honestly say that it wasn't just him being lucky... like always.
"How do you know their all so great, if you've only been with Annie?"
"Only been with Annie? No, I never said that. I was with a couple different ones before Annie. Two or three actually, and they were all great, it's just Annie is my one and only, that's all."
Okay... so maybe he had enough experience to say for sure. Now, I was really starting to consider this. "Alright, fine," I said finally,
"I'll go."
"Great, that's awesome, I promise you're going to love this place," he exclaimed excitedly.
"Listen, me and Annie will be there this Friday night, come on down and I'll take care of you man, I'll find you a real sweet girl."
We talked a little while longer and finally around 12:30 or so Rob left and I locked up the apartment before stripping down to my boxers and climbing into bed. I sighed, staring up at the ceiling, thinking about everything that Rob had told me tonight, and I hoped he was right. I hoped this turned out to be worth it, because I was really wondering right now why I had said yes.
Friday came a lot faster then I was anticipating, and by that point, I had decided I was just going to check this place out just to satisfy my friend. There was no real doubt in my mind, I was not going to be attracted to anyone there enough to hook up and have sex with them but there was no reason not to go just to have fun. Plus if I did not at least show up I was pretty sure Rob would be a little irritated with me for it.
So Friday after work, I came home and showered, before throwing on a casual t-shirt and a pair of denim jeans along with my converse sneakers. At about 7:00 I was out the door and in my car heading to the place he had given me directions to, it was called The Raven.
When I got there, I parked my car right around the corner and walked up to find Rob waiting outside smoking a cigarette, and who else did I find with him? The lovely Annie, at his side, smiling and having a seemingly very happy conversation with a few friends. As I got closer, Rob noticed me instantly and waved me over.
"Hey, what's up, I knew you'd be here!"
"Yeah, I told you I would," I said and we shook hands. He looked over at Annie and her friends and smiled.
"This is my buddy Jay. We've known each other since we were kids."
"Nice to meet you Jay," his girlfriend said. "I'm Annie."
"Nice to meet you too. Rob's told me a lot about you."
"Oh he did, did he," she asked in a joking manner and shooting Rob a funny look.
"So, I guess you know my little secret right?"
"Uh... yeah... not quite so little though, is it?" I said trying to make a joke.
It seemed to work as Annie, Rob and a few of the others standing around started laughing and so did I of course. They all seemed nice enough, I thought, and I felt myself relaxing a little bit. Finally, we all went inside and I was impressed at what I saw for the most part.
It was a pretty big place, lots of room to move around. There were two large dance floors and two bars in between. There was also a balcony, with a third bar on it and an extra set of bathrooms... then there was the basement. Rob told me that this was not your ordinary club, it was, but there were many rules that were allowed to be broken that some places would not let be broken.
In other words, this was your typical club, but a lot of people had a habit of hooking up and having sex HERE instead of leaving together and having sex back at one of their homes. Apparently, it was completely acceptable because according to Rob and Annie, the basement area was dedicated to anyone looking to have sex.
There were private rooms in which a couple, or sometimes more than just a couple, could go to have fun. I wasn't that impressed by that.
Surprised yes, but I did not actually come here to hook up with anyone, so that part did not really interest me.
Looking around though, I noticed there were a lot of women here. But then I remembered what kind of a club this was, and I found myself wondering just how many of them were actually genetic women. I figured the amount was probably relatively low, considering this place catered mostly to transsexuals.
"Hey, come on let's go get you something to drink," Rob said dragging me over to the bar.
I sat down and he got me a beer, and we started talking normally as though we were just back at my place instead of in the middle of a transsexual club. After about half an hour, I noticed that despite what I had told myself prior to coming here, I could not seem to help but look around at my surroundings... and a part of me liked what I saw.
A large amount of these women did not look like men at all. Mostly all of them were very convincing. There was a large variety of them too, white, black, Spanish, a few Asian here and there... it was a place that seemed very friendly to everyone.
I took a swig of my beer as I noticed the familiar tightness in my pants, and I realized that I was having a harder time not being interested in this place then I had intended on having originally.
"Hey, Jay check it out," Rob said breaking my train of thought. I turned around to face Rob only to find him standing next to me with an extremely attractive girl at his side.
She was tall, maybe about an inch taller then I was. She had shoulder length red hair, piercing blue eyes and a gorgeous body. Her clothing left very little to the imagination, a short skirt and a top that showed off a beautiful amount of cleavage.
Cleavage that almost made me forget once again, that this was not your typical club.
"Jay, this is a friend of mine. Her name is Lisa. Lisa, this is my buddy Jay, we go way back to elementary school."
I realized then she was actually one of the same people who had been out front earlier when I first arrived with Annie. That meant they were probably friends. She smiled, extending her hand to shake mine.
"Nice to meet you," she said happily.
"Likewise," I replied.
"I'll uh... just leave you two alone for a bit," Rob said standing up and walking away. I sighed, smiling and shaking my head. I pulled out a seat next to me so she could sit down and she thanked me.
"So Jay, tell me, have you ever been to a place like this before?" she asked.
"No... no, uh... this is my first time actually."
"Really, a newbie huh... Rob brought you here,
didn't he?"
We both started laughing, it was not necessary for me to give an actual answer, it seemed like she already knew the answer was a yes. We started talking and getting to know one another and I bought her a few drinks and we talked some more and before long I felt like I was really getting along with her. Then she said,
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I second that! I read this last night and found myself thinking about what happened next today lol
"Why don't I show you around and introduce you to some other people, would you like that?"
What the hell, I figured finishing off the last of my drink.
"Sounds good to me," I said standing up. She took me by the hand and led me to the other side of the bar and started introducing me to people.
The first person I met was a girl about the same height as Lisa, with blonde hair and hazel eyes and a body just as sexy as Lisa's was. Her name was apparently Jen.
After I met Jen, Lisa introduced me to a warm welcoming smile named Leslie. She was a brunette with a firm handshake reminding me that she was not like other girl's and her voice was a little deeper than a girl too. Despite those few minor differences, Leslie was still pretty attractive herself.
Then, there was Holly, a girl with hot pink hair and a beautiful smile. She had long smooth legs, green eyes, and a voice of an angel. Her breasts were not that big, she was relatively flat chest actually, but that did not bother me.
"So are you having fun Jay," asked Holly.
"So far, so good," I replied honestly. It was the truth. I really was enjoying myself. Between Holly and Lisa, I was having a very nice conversation when I decided I had to take a quick trip to the bathroom. Before I left, Lisa grabbed my arm and pulled me to her and whispered in my ear,
"Hurry up, and I'll show you the basement when you get back."
I knew what that meant, because I knew what the basement was mainly for since Rob had told me all about that part already. That meant I had a decision to make. I had come here intending to have just a good time hanging out and meeting new people. Rob of course intended for me to hook up with someone from the start, but I had been unsure of that.
Now that I was here though, now that I had met all of these beautiful women... Lisa included... I was actually second guessing whether or not I wanted to spend my night just talking.
I walked to the bathroom, thinking about all of this as I walked, trying to make up my mind before I got back to where Lisa was standing with Holly waiting for me. I emptied my bladder, splashed some cold water on my face and stared at my reflection in the mirror for a moment.
"Now is the time Jay," I whispered to myself.
"What are you going to do? Make up your mind."
I pushed away from the sink and walked out of the bathroom, and as I did, a very tall and well-built looking deep dark-skinned woman came up from behind me and suddenly gave me a slap on the ass.
I jumped, obviously taken by surprise, and whirled around to face her. She grinned at me and spoke in a deep yet strangely feminine voice, "Fresh meat?"
"What?"
"You new here white boy?"
"Uh...y-yes," I replied nervously.
"Mm, I can see that. You got a nice ass though.
Anybody ever tell you that?" I gave no reply, and she giggled leaning in close to me. I could smell her perfume, and feel her hot breath on my neck as she pressed me up against the wall behind me.
Lisa's P.O.V.
I stayed with Holly and talked for a few minutes while Jay was in the bathroom. She seemed just as excited to have someone new here as I was, and we were having a good time talking about our new friend.
"He's really cute," Holly said.
"Oh god, I know, isn't he though? Such a cute butt too, Mm, I can't wait to get my hands on him."
"I bet you can't," she laughed. "But don't forget me, I want seconds."
"Hah, Hah, you'll get your turn don't worry, I think Jen wants in too."
We were both laughing and I was fantasizing about what it was going to be like when I finally hooked up with Jay, I could not wait.
"Do you think he'll be submissive?" Holly asked.
"I don't think so," I answered truthfully. I knew, full well that Jay was not interested in being penetrated, that was okay, I was a respectful enough person not to force him into anything he did not want to do.
But it was still nice to think about what it would be like, and damn did he have a fuck worthy ass.
"Uh-oh," Holly said, interr
"Uh-oh," Holly said, interrupting my thoughts.
"Looks like someone else has her eyes set on our new friend and his butt, and I doubt she's going to be as patient about it as you are Lisa."
I looked up to see what she was talking about, and immediately I saw Kendra, pinning Jay against the wall next to the bathrooms. Obviously, he did not look very comfortable, and I knew just by her gestures what she was trying to convince him to do. Kendra was someone who came to this club for one thing and one thing only... white men and their assholes.
"Shit, I guess I better go take care of this," I said anxiously.
"Yeah, I think that would be a good idea," Holly chuckled.
Jay's P.O.V.
My heart was racing in my chest as she ran her hands down my back and started rubbing my ass, squeezing it and massaging it. I was completely frozen.
"I really... really love virgin ass,"
"To bad," Lisa interrupted, "Cause he's all mine. We already had plans,"
The woman gave Lisa a dirty look and snickered, before backing away slowly and running her hands down my chest in the process.
"Maybe later then," she said before walking away.
I sighed, looked at Lisa and she started laughing at the look on my face.
"That was Kendra," said Lisa,
"She's one of the more strong willed divas in this place and she loves white boys more than anything. So watch out for her... unless your into that sort of thing."
"No, not really," I laughed nervously. "You really saved my ass back there, quite literally I mean."
We both laughed and she gave me a smack on the ass, making me jump.
"Well, I meant what I said too, I already got dibs on your anal cherry."
To that, I gave her a worrisome look and she looked back at me seriously for a few moments, before breaking into a fit of laughter once again.
"Don't worry Jay, I'm kidding. If you do not want to do that, then it's fine with me, I don't mind. You'll meet and possibly hook up with a lot of girls here and you're going to find that mostly all of them are very accepting and respectful, I promise you that much, okay?"
"Yeah... thanks,"
"No problem... now... how about I show you the basement like I said?"
"Sounds good to me."
Lisa took me by the hand and led me down the long spiraling staircase to the basement area. I was surprised to see how big it was down there. There was a long, wide-open hallway with doors on either side of the hall, the floors were marble, the lighting was a dimmed and there was plenty of dance music blasting through the stereo system.
We walked down the long hallway and as we did, I felt my heart beginning to speed up again, I wondered what was going to happen once we found a room.
We stopped just outside the last door all the way at the end of the hallway and Lisa smiled at me before she took hold of the doorknob, opening the door. She motioned for me to step inside, and I obeyed.
Once inside, I was met with a small comfortable looking room, the floors were still made of marble. The lighting was a little brighter, and there was a small love seat on one side of the room and a comfortable looking mattress for two with silk sheets on the opposite side.
"Take a seat," she motioned towards the loveseat.
I sat down slowly, sinking into the chair, it was extremely comfortable. But it did very little to calm my nerves I realized, as I began tapping my foot quite heavily and nervously. She smiled at me shutting and locking the door before moving closer.
For the first time I really saw just how beautiful she actually was, her whole body was incredible. She leaned in close, placing her hands on my knees and smiling. I could smell her sweet scent and I had a perfect view of her cleavage.
She had glitter sprinkled on her breasts and a little on her neck as well, and it made her look like she was sparkling in the light that shone upon us both.
"You want to have some fun baby?"
"I... I would love that,"
"Good... so would I... I'm going to rock your world!" Lisa exclaimed.
She strad
She straddled me, sitting on my lap facing me and started grinding against me with her arms wrapped around me. She was giving me a lap dance, and the feeling of her ass moving against my cock, even if it was through my pants, was a feeling I welcomed happily. I put aside all of my fears and went along with it excitedly.
Eventually, she turned around, her back facing me and continued grinding up against me. She leaned forward some, giving me a perfect view of her beautiful ass, it did not look like a man's ass at all, and that was for sure. She even let me touch her, and her cheeks were just as smooth as a real woman would be.
She went back to facing me, and then she closed the gap between us and I felt her soft, warm lips press against mine. Her tongue probed at my mouth, until I opened my lips granting her access. My tongue and hers were now locked in a wrestling match, our soft moans filled the room as we explored one another.
We broke the kiss and she went right for my neck, licking, sucking and kissing, leaving a very, obvious hickey in the place of her lips.
Eventually Lisa slid off of my lap nice and slow onto her knees between my legs. She started rubbing me through my jeans and I felt my cock stiffen even more than it already had. Slowly, she unzipped me and reaching inside, freed my throbbing erection from its restricting confines.
She took me in her grip, a very firm and perfect grip, moving her hand up and down the length of my shaft to start. With her other hand, she started massaging my balls and I sighed, leaning my head back and giving in to the wonderful feeling.
Up and down, she moved her hand, stroking me and playing with my balls, until finally I felt Lisa's warm wet tongue flicking the head of my shaft.
I jumped at first, but then groaned as she flicked it once again. Almost as though she were getting a taste test, she licked the head like it was a lollipop, and I absolutely loved the feeling of her work.
Finally, she took me in her mouth, and I was in heaven. Up and down her head bobbed, her warm wet lips gliding back and forth over my cock. She could deep throat like a true expert, gagging only a little. She took me all the way into her throat, and it felt as if she were trying to swallow, the muscles in her gullet massaged my cock and it was the best feeling in the world.
This had to be probably the best blowjob I had ever received,
She started working me a little faster now, and I could feel the old familiar feeling of pressure building up in my balls, she sensed it coming to. Just as I was about to unload, she stopped, and I looked down at her surprised and almost disappointed, and she simply smiled back up at me.
"Why... why'd you stop?"
"I wouldn't want you to cum to soon, now would I?"
I sighed, as I felt the pressure decreasing, and when she realized I had recovered, she went right back to sucking my cock again. She started out the same as before, moving slowly, working me up to that agonizing feeling of pressure, and then once more as I was about to blow... she stopped.
It was like torture, she had me right where she wanted me the whole time,
Finally, the torture stopped though when she stood up and reached for her purse. Out of her purse, she pulled a Lifestyle Condom, along with a bottle of Astro-Glide. If this meant what I thought it meant, then I was very happy that she had not made me cum too soon, because I was certain it would be great. I had never actually fucked a girl in the ass before, though I had always wanted to try it at some point.
None of the girls I had dated in the past were open to the mere suggestion, and so I had been forced to forget that desire...until now. Maybe Rob was right, maybe this was a very good thing indeed.
She slowly pulled her skirt down, along with her silk white panties and for the first time I actually got to see another cock besides my own, she was not actually very big to be honest. Maybe around six inches, she wasn't one hundred percent hard yet, but it still was not such a bad sight.
As she started to kiss me though, I felt her cock responding, growing harder against me and when we broke apart and I looked down I was surprised to see she was a little bigger then I originally thought. She must have actually been about seven inches, pretty impressive really... but I still was not looking to do anything sexual towards her when it came to her cock.
"Don't worry about that," Lisa said motioning down to her member. "Like I said, nothing you don't want to do, you have my word."
"I trust you on that,"
"Good... I'm glad. Now, let's have some real fun."
She handed me the condom and I tore open the package, unrolling the latex over my hard cock while she poured a glob of lube into the palm of her hand and reached behind her to smear it all over her asshole. She turned around to face me, giving me a good view of her ass.
She bent over some, spreading her cheeks with one hand and let me watch as she smeared the lube all over her hole. She inserted a finger into her ass, and started fingering herself.
After a minute, I watched as she carefully inserted a second, and a few minutes later, she had worked at third one into her hole. My cock was as hard as a rock at this point, watching her slide her fingers in and out of her wet asshole, glistening with lube.
She pulled them out finally, and applied an extra amount before handing me the bottle.
"Put some on just for good measure," she said motioning towards my cock. I got the hint, and poured some over my shaft, rubbing it in real good. The condom already had lube on it, but a little extra would not hurt I figured.
When we were both ready, Lisa stepped forward and once again straddled me, sitting down towards me. I felt my cock probing at her asshole as she draped her arms over my shoulders and kissed me passionately.
As we kissed, I felt her pushing down on to me, and then I felt myself glide right into her. God she was so fucking tight! I moaned into her kiss and she reacted with a similar sound to my own.
My hands moved down from her breasts to her hips, taking hold of her love handles and holding on tightly as she started to ride me. She moved up and down on my hard cock, sliding in and out of her hole, leaning in closer to me. I took in the sweet scent of this beautiful girl, loving every second of what we were doing.
I could feel her own throbbing erection mashed between our bodies against my stomach, it was an odd feeling, but I overlooked it.
After a few minutes, she lifted herself off of me, turning around as she bent over, and I stood up behind her. I took hold of her hips again, pushing my cock right back into her gaping hole and continued to pound her with long hard strokes.
Standing up now, she was moaning louder, her cock swinging back and forth between her legs with every thrust and her breasts jiggling each time I slammed into her. Something came over me, and I found myself reaching around and taking her erection in my hand. I gave it a firm squeeze and she practically cried out in pleasure.
I pushed deep into her and squeezed her cock at the same time, and I loved the reaction I got. Lisa's body seemed to tremble beneath me, and her anal muscles clenched my dick tighter.
"Oh, fuck Jay, fuck yeah... fuck me harder!"
I was not going to say no to that, so I started ramming in and out of her, pumping her cock in rhythm with my thrusts. We were both panting, breathing heavy, sweating and moaning. The smell of sex filled the room. I could feel myself building up to what was sure to be a very intense orgasm. I could feel her dick starting to pulsate in my hand and I knew she was just as close as I was getting.
I pulled out, threw her on to the mattress in the corner of the room and climbed onto the bed with her.
I lifted her legs, wrapped them around me and pushed straight back into her. In missionary now, I pounded her ass as hard as I could with every bit of strength I had in me. The bed shook beneath us, and we both started getting louder as our impending orgasms finally overtook the both of us together. It hit her first, and I loved the sounds that she made as it washed over her.
"Oh, oh fuck, oh god, yes, yes, oh yeah!"
I felt something hot and sticky splash against my stomach, and as she writhed around underneath me moaning and squealing in pleasure, I knew she had cum. Now, it was my turn. A few more powerful thrusts and I buried myself balls deep inside of her ass and exploded.
I gave a sort of animalistic growl as my whole body shuddered and my cock spewed cum into her rectum. The condom held it all back though, but it still felt just as good to her I could tell.
When I was finished, I pulled out and collapsed at her side, both of us panting as she laid her head on my chest and we stayed there for a few moments. I started trying to register what I had just done.
I had just had sex with a transsexual... a man? No a woman who just happened to have a cock, instead of a pussy... but that was okay with me. At this point, it had to be, hell I had just jerked her off while I was fucking her in the ass.
"So, what did you think," Lisa asked finally.
"That... that was fucking hot," I replied. She laughed and reached down, pulling the condom from my dick and tossing it in a trashcan next to the mattress.
She climbed on top of me and rubbed her gaping asshole against my now flaccid dick again, until I felt myself starting to get hard again. Just when I thought we were going to have another round, she slid down my waist a little and started licking her cum up from my stomach. I only just then realized, she had cum all over me. Not that it bothered me, but it was funny to think.
Once she had licked it all up though, she moved back up and kissed me on my lips, sliding her tongue into my mouth and letting me taste her semen. We parted our kiss and Lisa smiled seductively at me.
"How's it taste? It's all because of you, so I figure you have a right to see what I taste like."
"It's not bad," I chuckled. "There's not much taste really."
"Well, how about next time... you can try sucking me off?"
"Oh... uh... I don't know,"
"Oh, come on," she begged. Lisa now sounded strangely like Rob, as I couldn't help but laugh at that, and so did she.
"It's not like I'm asking you to bend over for me or anything, wouldn't you eat pussy?"
"Yeah... and I have... plenty of times."
"So your basically still orally pleasuring a girl, it's just a little different than it normally would be. Give it some thought, and we'll see what happens."
"Yeah," I replied honestly. "I'll think about it."
We got up and started to dress, and I took note of how patient Lisa really was being with me about everything. She had led me through a very sexual fun adventure, at a steady pace that was comfortable for me. And even though she was requesting a little more from me next time, she was making it clear to me that she would not be angry if I said I didn't want to do that.
Truth be told, I did not know if I wanted to do that or not yet. However, I would definitely put some thought into it, as I had promised her I would.
When I left the club that night with Rob, I told him that he was right. I had a lot of fun, and so far, I had no regrets. I told him about the incident with Kendra and he found it hysterical. That was typical Rob though.
I couldn't wait to come back to The Raven next week.
Bravo! Hell of a story man. Way to make an entrance into this world!
Quote:
Originally Posted by sweet_boy
Hopefully there is a part 3 and more
Kool read, I enjoyed it, almost similar to my first time down in a Tampa Tranny club back in the early 80:s
The next day, I woke feeling refreshed, like it was the start of a new life...I cannot explain it but it felt like a great weight had been lifted' from my chest. Some would consider that to be the typical feeling you get after being laid for the first time in months. Ordinarily, I would agree, but in this instance I felt as though it were something completely different from that.
I got out of bed, and walked to the bathroom with a smile to relieve my bladder. I glanced at myself in the mirror and noticed I had glitter on my bare chest and a hickey on my neck. I could not help but laugh, before turning on the hot water in the shower and climbing in to stand under the stream.
As I stood there soaking under the water, my mind drifted back to memories of what I had done the night before, at The Raven, with Lisa. I recalled how incredible she was at sucking dick, and how unbelievably tight her ass was... it had felt great when I fucked her. As these thoughts filled my head, I felt my cock starting to get hard and I reached down to grab hold of it, stroking it nice and slowly.
I imagined it was Lisa stroking it for me, instead of my own bare hand, and within minutes I was shooting a load all over the shower floor. I sighed, leaning back against the shower wall and laughed.
I was definitely looking forward to going back to the club again... maybe tonight. Rob had suggested it last night when he dropped me off here in his car, and I told him at that point I would think about it. But as of right now I was pretty sure I wanted to go back tonight instead of waiting a whole week.
I wanted another go with Lisa, and maybe a chance to get to know some of the other girls at the club a little better too. Except Kendra, who I was pretty sure I wanted to stay far away from and her intentions of seducing me. Once I was dressed, I picked up the phone and called Rob to see if he was still down for going back to The Raven again tonight.
It rang once, then twice, and then a third time and finally Rob picked up. He sounded like he had just woken up himself within the past half hour probably.
"Hello," he muttered.
"Rob... dude... let's go back tonight, man."
"Hah, Hah," he chuckled on the other side of the phone. "Dude, I'm definitely down... what time is it though?"
I glanced over at the clock on my wall, it was just past eleven thirty in the morning.
"It's going on lunch time soon," I answered.
"Cool," he yawned, "How about this, give me an hour and I'll swing by with Annie and the three of us can go grab something to eat too. Sound cool?"
"Yeah, definitely," I replied.
We hung up the phone and I decided to pass the hour by going online on my laptop. I intended on just checking my e-mail and Face book account, but as the thoughts of Lisa continued to flood my mind, I found myself looking up shemale porn. I stayed away from the ones that had anything to do with guys getting fucked, focusing on the beautiful, drop dead gorgeous girls who loved to suck cock and get pounded.
I started thinking, as much as I liked Lisa, I really wanted to spend some time with some of the other people at The Raven as well. I just hoped she was not going to take that personally or anything like that. I glanced again at the clock...
Rob would be here in about half an hour. I reached for my cell phone and opened up the phone book, pulling up Lisa's phone number. She had added it to my list herself last night before I left to go home.
I pressed the dial icon and put the phone to my ear, waiting as it started to ring. Five or six rings in, I heard a soft click followed by her beautiful voice.
"Hello?"
"Lisa?"
"Jay? I'm glad you called," she said, sounding excited, "I miss you already."
"Yeah, me too. I'm going to be at The Raven again tonight with Rob. Would you be there if I showed up? I'd love to see you again."
"Definitely, I'm there most weekends. Maybe we could have a bit of fun in the basement again if you're up for it... oh, and Holly and some of the other girls were looking forward to hanging out a bit as well."
There was a hint of jealousy in her voice, and I laughed. She must have realized that I had noticed her sarcastic tone of voice, because she started to laugh as well.
"Don't worry," she said, "I'm not going to hold you all to myself, besides I'm not exactly looking for a relationship right now anyway."
"Is that so?"
"Yeah, I don't know... it's just not for me, you know? Not at the moment, at least... maybe someday, I will be a little more open to 'falling in love' but right now, I just want to have some fun. With that said, if you're looking to have fun with some of the other girls too, I'm not going to act like the jealous girlfriend."
There was no hostility in her voice or resentment either, in fact, she actually sounded serious. That was a good thing... I had been nervous about bringing up this topic, but she had brought it up on her own. Not only that, it looked like it had also gone in the direction I was hoping it would go as well.
"That's cool Lisa... but tonight, I think I want to be with you again. There will be time for me to get to know Holly and the others. Maybe we could even have a threesome sometime together?"
I bit my tongue right after saying that, I felt like I had blurted it out without even stopping to think before opening my mouth. I hoped that I had not just ruined things for myself all together... I waited for an answer.
"I like that idea," she said, as I let out a heavy sigh of relief.
"It wouldn't be the first time Holly and I have had our way with a cute boy like you together,"
she giggled, "It's always fun when we do too."
"Awesome," I said happily, just then, I heard a car horn outside beeping and I cleared my throat,
"Well, I should go, Rob is here with Annie and we're going out to lunch and hanging out for a few hours. So I'll see you tonight?"
"Definitely,"
She sounded just as excited about our second encounter as I was, and we hung up the phone on a good note. I quickly put on my shoes and made my way downstairs and outside, getting in the back seat of Rob's car. He and Annie both greeted me and we headed off to a nearby burger shop for lunch. As we sat and ate, I told Rob and Annie that I had called Lisa before they picked me up.
I told them things seemed to be going great and I was excited to go back there tonight.
"So she's cool with you hanging with the other girls," Rob asked.
"Yeah, she even agreed to her and Holly possibly having a threesome sometime."
Annie laughed, "Yeah, those two love threesomes. You're going to get lucky all the time as long as the both of them are your friends Jay."
I knew she was right, and just the thought made my cock twitch in my pants. I could not wait to get back there tonight.
We left the restaurant together and drove back to my place to hang out, and watch TV for a couple of hours before heading out that night. It was probably around 7:00, like the previous night, when we made our way out the door and to Rob's car. We arrived at The Raven by about 7:30 and I made my way inside behind Rob and Annie who went straight for the bar.
I followed, not knowing for sure if Lisa was here yet, and took a seat with my two friends. I ordered a Jack and Coke. Since Rob was driving me home tonight, I could have a couple drinks if I really wanted to. I felt a hand on my shoulder, and turned expecting to find Lisa, but it was actually Holly and Jen.
"Hey," they both greeted me together, looking happy to see me.
"Hey, how's it going," I answered just as excited to see the both of them.
"Back again huh," asked Holly.
"Yeah, I couldn't stay away," I replied, "I had way too much fun last night."
"I bet you did," Jen winked and we all started laughing. Both girls sat down, joining us at the bar, and I treated them each to a drink on my tab.
We talked for a while and before I knew it, it was getting close to 9:00 at night... I wondered if Lisa was going to show up tonight or not. She said she would be here, but maybe something else had happened and she could not make it.
No sooner had the thought crossed my mind, than my cell phone started to ring in my pocket. I pulled it out and looked at the caller ID and sure enough, it was Lisa. Nervously, I picked up and placed it to my ear.
"Hello?"
"Jay... hey, it's me."
"Hey, where are you?"
"I can't make it tonight," she said, as I noted how she actually did sound rather disappointed herself at this sudden turn of events, "My car broke down, and I wound up having to stay late at work too, and I'm really tired. I could catch a cab but I am absolutely exhausted."
"That's okay," I said, really wishing it had not turned out this way.
"Stay home and get some sleep, I'll be here again next weekend and we can get together and have some fun again then, sound good?"
"Absolutely, and Jay... listen... if you want, you could spend some time with Holly or one of the other girls instead tonight. Like I said, she's wanted a chance to have some fun with you as well anyway."
I looked over at Holly, and she winked at me and I laughed slightly. I thanked Lisa for calling me and told her that I hoped everything worked out with the car before next weekend, and if she needed anything to call me. We hung up, I set the phone down on the bar counter, and Holly glanced over at me.
"That was Lisa? She on her way yet or no?" She asked.
"She can't make it... her car broke down and she's really tired."
"Awe, what a shame," she said trying to sound disappointed, and I laughed at how easy it was to see through her little act. She giggled and scooted closer to me and began flirting a bit more heavily than before.
"No, but really... I love Lisa. She's my best friend, and she wouldn't mind."
"No, she wouldn't actually," I agreed, "She told me to go ahead and hang out with you tonight instead."
Holly's eyes lit up and she started to laugh.
"I told you she was my best friend," she said and I smiled. We continued talking for a while longer, the night wearing on and I could see the whole time that Holly kept checking me out.
Eventually, Jen got up and walked off to the dance floor, leaving Holly and I alone. Holly then looked over at me and winked. I knew what she wanted, and I wanted it just as much, I was feeling the alcohol, and when I get drunk or even a little close to drunk I usually get horny.
So when Holly stood up and took me by the hand, I offered no resistance, sliding off the bar stool and following her towards the winding staircase. Down into the basement we went and took one of the first rooms on the left hand corner of the long hallway. This room was different from the one Lisa and I had shared the night before; it was a little smaller and instead of a couch, chair and mattress, there was only a mattress.
Holly shut the door and locked it. I sat down on the edge of the bed and she walked over to me smiling as she then did a nice little sexy dance for me. She was showing off all the sexiest parts of her body as she danced. She was wearing just the right clothes to show me the right amount of cleavage. Her legs looked smooth and beautiful, and she brushed a strand of her hot pink hair out of her face before sitting down on my lap.
I held her close, and she pressed her lips to mine, sliding her tongue into my mouth. I kissed back as we embraced one another in a heated make out session. That lasted about a minute and a half, before she slid off my lap and on to her knees. She undid my pants, and I leaned back on the mattress as she pulled them down around my ankles, my throbbing erection sprang free. Holly wasted no time, wrapping her lips around my member and swallowing me whole.
She bobbed her head, sucking, slurping and stroking and I groaned... she was just as good at this as Lisa had been. She cradled my balls, massaging them with one hand as she sucked me hard, and rubbing my inner thigh with her other hand. She used that same hand to slide up my stomach to my chest, lightly pinching and squeezing my nipples.
"Oh fuck," I moaned, "You're so good at this, suck my cock!"
I was running a hand through her pink hair and she responded by picking up her pace, bobbing her head faster, and then deep throating me. I could feel myself getting closer and closer to the edge of an orgasm, and when it finally overcame me I swore so loud that I was certain whoever was in one of the rooms next to us would be able to hear. Not that it mattered, anyone next-door would be doing the same.
I fired off several ropes of hot sticky cum down her throat, she swallowed all of them with excitement and vigorously licked the head of my shaft and the shaft itself clean. Then she moved up, getting off her knees and kissing me on the lips again. I could taste myself on her breath, and I moaned into her passionate kiss as she took my hand and led it to her crotch.
I rubbed her through her denim skirt and she sighed, breaking the kiss and leaning her head back as I massaged her.
"Jay," she whispered, "I want you to take my skirt off."
I quickly obliged, moving both hands to the hem of her skirt and hooking my thumbs under the edges. I slowly pulled it down over her smooth legs. She lifted one foot and then the other slipping out of it all together. I threw it to the floor and watched as she stepped back and hooked her thumbs under her pink panties. She slipped out of them as well, threw them aside and turned to face me again.
Now I could see her cock, and she was actually pretty big. She must have been about seven or eight inches, and she was already fully erect and ready to go with a tiny bead of pre-cum leaking from the head of her shaft.
"So... Jay,"
"Yeah,"
"Have you ever sucked a cock before?"
Oh boy, I thought, here we go. I should have seen that question coming along without any trouble, but it still had come out of nowhere. Holly definitely seemed a bit more determined to get what she wanted then Lisa was, and I was positive if I made it clear I did not want to do this, she would back off.
However, I was also sure she would do everything she could to convince me before I got to the point where I did make it clear I was not interested. As she took her huge cock in her hand and started stroking it though, something came over me and I found myself wondering... did I want to say no?
"Uh... n-no,"
"No? Well, I think it's something everybody should try at least once."
As she said that, she inched closer to me, and I just sat there completely frozen in place. Her dick was huge this close up and rather fat too. She stopped right in front of me, her member just an inch away from my mouth. She started to stroke my cheek, holding my gaze, and then ran her hand through my hair before probing my lips with her cock.
As she poked my lips with her throbbing member, I inhaled the musky aroma of her genitals and found my own dick growing hard once again. I had come to this club with no intentions of submitting to anyone, and yet here I was, giving in to temptations, about to suck a dick.
What the hell, I figured, it was not as if I was taking it in the ass. I could perform oral sex on her or most women I might hook up with in this club, it did not mean that I absolutely had to bend over and let them fuck me just because I sucked their cock.
Giving in, I opened my mouth and she pushed her erection between my lips. She tasted a bit salty, but it was not very bad of a taste to be honest. I almost felt like I actually enjoyed it as I closed my mouth around her and she took a handful of my hair and lightly pulled at it. As she pulled my hair, she started thrusting her pelvis, pushing her cock in and out of my mouth. It was as if she was fucking my mouth. It was an odd feeling, but I was enjoying it still.
"Mm, yeah, that feels so good, you sure you've never done this before Jay? Because you are too damn good at it to have never sucked dick,"
"Mmmf," was all I could get out with her huge dick rammed down my throat. She giggled and that is when she started to pull my hair a little harder and as she did, she started pushing deeper into my gullet trying to get me to deep throat her.
I choked and gagged as she touched the back of my throat, and after a minute of forcing herself down my throat, I felt saliva running down my chin. She moaned, pushing her cock all the way in and holding that position, I could feel her big, warm balls against my chin.
"Oh fuck, I have to stop or I'm going to cum," she moaned. She pulled out of my mouth and I gasped for air, breathing heavily.
Holly smiled and laughed a little handing me a tissue to wipe away the spit.
"Your really good at that," she repeated her earlier compliment, with great satisfaction in her voice.
"It's a shame your not interested in being fucked, if your that great of a cock sucker, I can only imagine how good it would feel to shove my dick up that tight little virgin ass of yours."
"Thanks," I said my voice a little scratchy, "But I don't think so... maybe someday, but I'm not interested at the moment."
"That's okay, I'm not pushy. So what do you want to do next?"
To be honest, I had my eyes on her ass almost the whole night and as they drifted back to that part of her body, I felt my cock grow rock hard again.
"Why don't you come ride my dick," I suggested.
"Ooh, sounds fun to me baby," she replied. She reached into her purse and pulled out a bottle of Astro-Glide and a condom, handing me the condom. I lay back on the soft mattress, my throat sore. I tore open the package and prepared myself while Holly was busy lubing her asshole up nice and good. Once we were both ready to go, the bed shifted as she climbed on to it and straddled me.
I could hardly wait until I was inside of her...oh fuck, she was so tight, Just like I had imagined, as she lowered herself down onto me, my cock pushing into her hole, I practically came right then and there.
She must have known how much control she had over me, because she seemed to be slowly inching her way down my pole with a big sexy grin sprawled across her face, it was as if she was trying to torture me by slowly applying herself to me rather than diving right in as I wanted.
"You're so big,"
"And you're so tight... fuck... your ass feels so good Holly."
"Why thank you baby," And with that I got my wish, as she slammed herself all the way down onto my cock until I was buried deep inside of her. I grabbed her by the hips and she started bouncing up and down on me, my dick sliding in and out, her tits jiggling, the bed shaking underneath of us.
The room was filled with the smell of sex and the sounds of passion, as we both moaned and sighed in pleasure. Soon, she was begging me to fuck her, and I had flipped her over into missionary so we could look each other in the eyes as I started to pound her with long, hard powerful strokes.
Her own cock was resting against her belly, leaking pre-cum and every time that I slammed into her, it would shake; it was a sexy view. One that fueled my aggression, and I picked up the pace fucking her harder and harder.
She dug her nails into my back, screaming my name and I felt myself building up towards the end. She was already there, I could tell judging by her passionate moaning and how her body kept trembling like a leaf underneath of me. A few more powerful thrusts and she cried out, her cock jerking, shooting a massive load of hot, sticky cum all over her own belly and her tits.
I lifted her legs up all the way and started pushing as deep into her as I could get without harming her. Finally, about a minute later, I howled in pleasure as I exploded deep inside, trying to fill her with my own cum. When it was over, I collapsed onto her and she wrapped her arms around me and held me, as though she were actually my lover. It was a comfortable feeling, and I found that I really enjoyed it, almost more than the sex itself. (Continue)
I pulled out finally, my cock had gone limp. I removed the condom and tossed it before lying down beside her. Holly snuggled closer to me and we simply stayed like that for a few minutes, our sweaty bodies pressed together.
"That was a lot of fun," she was finally able to say.
"Yeah... I'm so fucking tired now," I laughed and so did she. We finally got up and started to dress, and I looked at the clock on my phone... it was almost 1:00 in the morning and I had missed three calls from Rob and one from Annie.
"Shit," I swore under my breath.
"Everything okay?" Holly asked.
"Yeah, I just didn't realize Rob was trying to call me. I hope he didn't leave without me... I didn't bring my car tonight and I'm screwed if he did leave."
"Well, let's hurry up and go find him."
We left the basement and thankfully, after some searching, I found Rob and Annie outside smoking a cigarette. Rob was drunk, but Annie was sober enough to drive in his place. I gave Holly a hug and a kiss, said goodbye and the three of us left, getting into Rob's car with Annie driving me home.
The next day was Sunday. I woke early, around 9:30 am or so and got up to start doing my wash and some other Sunday activities. I took a shower, packed my laundry bag and made my way out to the Laundromat.
The whole day that I spent there, I spent it thinking about everything I had done the last two days, I'd had a lot of fun with Lisa on Friday, but I almost felt like I had even more fun with Holly last night. Not that I liked Holly more than Lisa, or Lisa more than Holly, truth be told, I could have probably had almost as much fun with Lisa if I had said yes when she asked me to suck her cock.
I told her I would think about it and maybe do it the next time, which would have been last night, but her car broke down and so I wound up doing it with Holly instead. Although, I had never originally intended on sucking her cock... I just planned to have sex with her. But stuff happens sometimes.
I got home from the Laundromat around 7:30, put everything away and made dinner before going to bed around 10:30 that night. I had work in the morning and I was really hoping that this week would go by as fast as possible. Then I could get back to The Raven on Friday and hang out with both girls this time.
I got my wish, the week went by fast. By Thursday night though, I realized I had not spoken with Lisa since Saturday when she called to tell me she could not make it to the club. I decided to give her a call Thursday night and ask her if she wanted to come over, spend some time together and have dinner. I called and she picked up, sounding happy to hear from me.
"I was wondering if you would want to come have dinner at my place."
"Tonight? I would love to, but I have work in the morning. I will be at the club tomorrow night for sure though, my car is fixed, see you there?"
I hung up feeling a bit disappointed, and went to bed early, I just wanted tomorrow night to get here as fast as it possibly could. Friday morning I woke up and took a shower, got dressed for work and was out the door by 8 am.
Work flew by, lunch break came before I knew it, and when I sat down and checked my phone I saw that I had a voicemail from Lisa. I punched in my voicemail password and put the phone to my ear.
"So you little cock sucker... I heard all about what you and Holly did last Saturday. Call me back when you get this, okay?"
"Shit," I thought nervously, "Is she pissed off at me? I thought she was okay with me hooking up with Holly, she said it herself that it was okay."
I thought that maybe I had misunderstood her or something... I only hoped she was not too angry with me, as I did not want to lose her friendship. I dialed her number and the phone rang three times before the click of someone picking up signaled that I was about to find out for sure if she was pissed.
"Hello?"
"L-Lisa... its Jay,"
"Hey there you," she said. She definitely did not sound too pissed off, but I was still a little paranoid because of the voice mail she had left me, "How's it going?"
"It's... okay. Listen, I got your voice mail... I'm really sorry."
"Sorry? No, its okay, I'm not angry with you," Lisa said.
I let out a heavy sigh of relief and leaned back in the chair I was sitting in. I was definitely very happy to hear that she was not pissed off at me as I had assumed she might be, "That's great, because I was pretty worried you were."
"Of course not Jay, I told you it was okay for you to have some fun. I just didn't expect you to be willing to do anything like that with her."
"Yeah...it was kind of a spur of the moment decision," I said laughing nervously.
It was not a lie, I had not gone into the basement with the intention of sucking Holly's cock. Sure, I had enjoyed it, but it was not planned.
"Did you have fun?"
"Well... yeah, it was cool, I liked it."
"Good... because tonight, I want you to show me what Holly taught you, got it?"
I laughed and quietly hinted that it was okay with me, and a few minutes later we hung up so that I could return to work. I was happy to know I was off the hook, that Lisa was not mad at me, as I imagined she was. The only thing she expected was for me to do for her what I had done for Holly.
In spite of the fact that I had already done it once, and even enjoyed it to a point, I was still nervous about doing it again and this time with Lisa. It was only fair though, I had promised her I would think about it and wound up doing it the first time with Holly when it should have been Lisa who got the first chance.
The rest of the workday went by quickly, and before I knew it, and the day was over with, thankfully. I clocked out and made my way home to get ready for what I was sure was going to be another exciting and fun night at The Raven.
When I arrived home, I stripped out of my work clothes and went straight for the shower making sure to clean up real good. I brushed my teeth, put on some fresh clothes and sprayed some cologne to add to the style. When it was all said and done' I waited for Rob to show up with Annie.
When they finally got to the apartment, I met them outside and we decided to go to a restaurant and get something to eat before heading to The Raven.
An hour and a half later and we had parked the car up the street from the club like usual and were making our way towards the front entrance. Rob and Annie were all over each other like they normally seemed to be, and I was very excited to get inside and meet with Lisa.
I found her at the front door with Holly and Jen smoking a cigarette. She smiled and waved at me as I got closer to the door with Rob and his girl, and she put out her cigarette and met me halfway with a big hug and a kiss on the lips.
"I'm glad to see you, I missed you," she said giggling.
"Likewise," I replied. Holly looked over at me and winked, and I blushed. Lisa laughed and gave me a nudge towards Holly who proceeded to pull me into her arms and give me a hug as well.
"I heard you were convinced Lisa was going to be pissed at you?"
"Yeah... I guess I was wrong though, what a relief."
"Lisa rarely ever gets mad," Holly said, laughing,
"And besides, we've always enjoyed sharing our men equally so of course she wouldn't mind."
"No, I didn't mind," Lisa chimed in innocently. "I just want to see if you're as good at sucking dick as Holly claims you are."
I blushed as she took me by the hand and led me into the club. We sat down at the bar and ordered a couple of drinks. No rush, Lisa said. It was only 8:30 at night so it was easy to sit back and have a few drinks before heading off to the basement to have fun together.
"So how've you been," she asked, completely skipping over the topic we had been on just a few short minutes ago. That made me feel a little less anxious to be talking about something unrelated to what we were going to be doing in an hour or two.
"I've been okay, I just really missed you. I'm glad you made it tonight."
"You're so sweet," she teased me.
"You know it occurred to me recently, that I don't know much about you. So, tell me about yourself Lisa."
"About me, what do you want to know?"
I told her to tell me whatever she wanted, and she smiled and started to tell me her life story. Apparently, she had grown up in New Jersey, right across the bridge. When she was a boy, her name was Joseph; she lived her life as a man until she was eighteen years old when she moved out on her own. From there, she started dressing as a woman and eventually started doing it full-time...now at twenty five years old herself, she had been living full-time as a woman for the last seven years, quite happily too.
When she was done explaining, I felt happy to know more about her then just the sexual side. I hoped to get to know some of the other girls as well... I enjoyed being here, but I did not like the idea of just having random sex. I liked to know that these people were my friends as much as they were my sexual partners. And I wanted them to know that I was their friend too.
Eventually though, it came to the point where Lisa wanted to get to the point. She had moved off her bar stool at some point, and was now resting on my lap, flirting with me. That turned into us making out together and she took me by the hand and guided it down to her leg.
I ran my hand up her smooth leg and under her skirt to find she was wearing no panties, and damn was her cock hard as a rock. I stroked it slowly at first, then a little faster and she moaned biting me on the neck.
"C'mon lover boy," she whispered in my ear. "Show me what Holly taught you."
We made our way into the basement and picked a room and once inside, Lisa pushed me against the wall and crushed my lips with her own. Her tongue slid into my mouth in a passionate French kiss, and I held her close to me. I could feel her cock poking me even through our clothes.
I decided it was time for me to take control, I still was not very good at this, but I was eager to please. I broke the kiss and guided her towards the mattress, where she sat down at the foot of it and I got down on my knees.
Excited, she lifted her skirt and there was her raging hard cock. She leaned back on both hands and watched lustfully as I took her in my hand and started stroking. "Mm," she moaned. "Nice way to start off, I suppose."
"Don't worry, it'll get even better," I assured her.
"I'm sure it will," she said in a seductive voice smirking at me.
That was my cue, I thought, as I leaned in close and started off by giving the head of her shaft a lick. She tasted like strawberry body wash, it was great to know she had cleaned up before coming here, and had even used a type of soap that would taste good. I continued teasing, licking the head of her shaft, before I started licking up and down her shaft and over her balls.
I started focusing on her balls, licking them each one at a time, before taking one in my mouth and sucking on it. Lisa moaned louder this time, and as I sucked on her one ball I stroked her cock as well. I released her left ball, and then moved to her right one sucking on that one for a few moments.
"Oh god," she muttered, "So far I'm not disappointed Jay... but please, get to the damn point already," she laughed.
I released her right ball and moved back up a little to the tip of her shaft before finally sealing my lips around her. She gasped as I did, and I took her as far down my throat as I could before I started to gag.
I pulled back some, then moved back down a little further choking once again. I kept pulling back and moving back down every few seconds and each time I managed to take more of her to the back of my throat.
Soon enough, I had all seven inches of her raging hard-on in my mouth, deep throating her with slight difficulty. Every couple of seconds I would choke or gag, but I was certainly beginning to get the hang of this I thought.
Lisa seemed very impressed at my efforts as well. She was now running her hand through my hair, her head leaned back, her other hand pulling at the silk sheets and groaning as I continued sucking her cock as best I could. She tightened her grip on my hair eventually, and began moving my head up and down on her shaft as though she were guiding me. The realization that she was taking control of the situation seemed to turn me on more.
"That's good Jay, I like that, just like that baby."
Hearing her approval, I began moving up and down faster, and also added a hand to cup and massage her balls for a few moments. I moved that same hand up her belly to her breasts and began to massage her left breast, pinching and squeezing her nipple. Her breathing started to get heavier and she started thrusting her hips upwards, pushing her cock in and out of my mouth now.
"Fuck baby, keep that up and I'm going to cum real soon,"
That's exactly what I wanted to happen, and so I did indeed keep it up and as I did I noticed her reaction increasing. She was moaning louder now, her breathing heavier and faster and pulling on my hair.
"Fuck, yeah, oh god I'm going to cum," she warned me, "Pull off, I'm going to cum!"
I did not back off though, if she was anything like me I was pretty sure she would enjoy the idea of being able to cum in my mouth. So I kept my lips firmly wrapped around her took and within moments I felt her entire body begin to shudder.
"Oh shit, here it comes," she cried out in pleasure.
I felt her erection begin to pulsate, and then I felt the hot sticky cum flowing into my mouth.
This was the second time I had sucked cock, but it was the first I had actually tasted cum. When I went down on Holly, we had stopped before she reached her orgasm and so I had not had that experience at all until just now.
To be honest though, there was not much to it. It did not have any notable flavor that I found enjoyable. But it was not disgusting either, nevertheless, I enjoyed the idea that I had allowed her to cum in my mouth, and I swallowed every drop to further satisfy her.
"Oh wow," she sighed feeling relieved, then teased me as I licked the head clean, "That was hot, and you swallowed it all too, such a good boy!"
I pulled away and she pulled me up to eye level kissing me on the lips, sliding her tongue into my mouth.
"Want to fuck me," she asked seductively.
"That shouldn't even be a question, of course I'd love to."
I flipped her over onto her back and she cried out in shock, and then started laughing. I fumbled with my belt and zipper, sliding out of my jeans and boxers. I did not bother to remove my shirt right away, and likewise, Lisa remained in her clothing simply lifting her skirt further since she had no panties.
I lifted her legs and moved between them, kissing her passionately and probing her asshole with my raging hard cock.
We both moaned, and I pushed forward, my dick slipping into her hole, which surprisingly was not very tight. She must have been playing with herself before she came here tonight in an effort to loosen herself up in advance.
I still swore though that her ass was tighter than any pussy I had ever fucked, and it felt just as great as last time and just as great as Holly's ass felt.
"Oh god, fuck me," she cried out. I started pounding her ass, legs wrapped around my waist, the bed shaking underneath of us and the both of us were moaning in pleasure and gasping for air
She moved both hands up under my t-shirt over my back, racking my skin with her nails and biting my neck. In and out of her ass I thrust, building myself ever closer to the inevitable orgasm I wanted so badly. She reached down between us and started stroking her own dick as I fucked her, and soon we were both right on the edge.
"Are you going to cum," she asked, breathing heavy.
"Oh shit, I'm almost there."
"Pull out," she said desperately, "I want you to cum in my mouth."
I wanted to finish in her asshole, but I could tell she really wanted it and so I figured I would give her what she wanted. I withdrew from her ass and moved up some so that I was right up in her face. I started stroking my cock, but she slapped my hand away and instead pulled me to her wrapping her lips around me. I bit my lip, moaning, and then I felt something I had not quite expected to feel.
I felt her finger probing my asshole; and then I felt it slip into me. It was not painful, a little strange at first but once she found that spot, the right spot; the prostate gland...there was no turning back for me.
Keeping my dick in her warm wet mouth, and her finger pressed firmly against my prostate, Lisa had me right where she wanted me. I felt my body tense up, my dick begin to swell, and finally I burst inside of her mouth. Huge globs of semen blew from the tip of my member shooting right down her throat and I sighed as I felt the tension leaving my body.
After she had swallowed it all, Lisa released my cock from my mouth and I felt myself begin to go limp. My whole body loosened up, including my backside and I felt her finger slip a little deeper into me.
"You like that baby?"
"Mm... it's not bad," I replied truthfully. It was not the greatest feeling in the world either, but I could not deny that it did feel good. It had certainly added to the intensive orgasm I had just experienced, which would have been great even without stimulating my prostate, but I was not complaining.
She continued rubbing that spot for a few moments and then started moving her finger in and out of me. I moaned softly and she flipped me over onto my back, I snapped out of the post-orgasm state I was in and realized the awkward position that she had me in now. I was in the same position she had been in just a few minutes ago while I was fucking her, and on top of that she still had her finger in my ass.
"H-Hold on," I said.
"Shh," she pressed her other hand to my lips. "It's okay... I won't take it that far if you don't want me to. I'm just giving you a little massage is all,"
I trusted her enough to know she was serious when she said she would not go too far unless I wanted it to go that far. There was nothing wrong with what she was doing right now as long as it stayed where it was.
Plenty of guys out there enjoyed prostate massages, I had read up on it a few times in the past. It did not mean you were gay or bisexual even, it was just another way of getting off and a lot of' men felt like it was worth it too.
Hell, I had had a girl a few years ago offer to do it for me, a genetic girl. I had been too much of a chicken shit at the time to approve it, but now I was wondering why I had not gone through with her offer, because this did feel pretty good.
I noticed my cock was hard again, sticking straight up at full attention as she continued to massage my inner spot.
With her other hand she started rubbing my nipples for a few moments before replacing her hand with her lips. Sucking, licking and biting my nipples, she had me writhing underneath of her in pleasure as pre-cum began to leak from the tip of my cock.
As I felt myself building up to yet another and possibly stronger orgasm, I realized that Lisa was not even touching my dick; she was simply focusing on the prostate massage and using her lips to lick my nipples and now my neck as well. Then it hit me with overwhelming force as she sped up her hand motions and started sucking on the left side of my neck hard.
My whole body locked up and I gasped for air as a hot burning sensation shot through my cock and I spewed another hot load from the edge of my member, this time all over my chest. I had certainly come that much in the past, but never so hard; I let off at least six or seven straight shots.
They went high up into the air to before falling back down onto my chest. As she continued biting and sucking my neck, I heard Lisa giggle' before backing away from me. (continue)
"I think you enjoyed that one too, huh?"
"Yeah... it felt good."
She pulled her finger from my ass and gave me a soft kiss, before climbing off the bed and I sat up, my legs shaking. My ass was a little sore, but nothing serious. She had used her index finger and I suppose it was not that big, which was probably why the pain was so light.
"You okay," she asked looking at me concerned. I had not moved or spoken since she got off the mattress, and she was beginning to worry a little.
"Yeah, yeah I'm fine," I said trying to calm her fears, "I'm just... trying to register how that actually felt so good, you know? It was a new experience for me and I guess I just didn't expect it to be so fun."
"I'm glad you enjoyed it, because I know I did."
I laughed, standing up finally on my wobbly legs and stretching a little.
"Don't get me wrong," I said. "It's not like I'm going to bend over and let you fuck me or anything. It's just that one finger felt pretty nice I guess."
She laughed, "Well, I'm not expecting you to baby. Like I said, it wasn't about getting you to let me do anything your not interested in. If I were a genetic women and I tried to do that, it would have probably felt just as good."
"Most likely," I laughed slipping back into my boxers and jeans.
Once we were both situated, we made our way back upstairs to the bar and I bought myself a beer to try to take the edge off a little. Not that I was regretting it or anything, but I was still feeling a little shaky and surprised at my own bodies reaction, As I sat down at the bar with Lisa sitting to the left of me, Holly came over and sat down to the right of me.
"So," she said looking over past me at Lisa, "Was I right, or was I right?"
"Oh god, were you right," she said and both girls started cracking up. I blushed and laughed as well, taking a swig of my beer.
"So Jay... what are you doing tomorrow," Holly asked suddenly.
"Oh... uh, nothing that I know of, do you want to meet up here again?"
"Actually," she said, "I was thinking maybe the three of us could meet up and hang out somewhere else for the day. Might be a nice change from our usual surroundings here."
I noticed a certain look Holly was giving Lisa, and that Lisa seemed to fully acknowledge whatever the other girl's eyes were trying to suggest. They were both smiling at each other, then they both looked at me in a rather lustful manner and I chuckled, shaking my head, and catching the drift.
"If you're up for it, there might be something extra fun in it for you," Lisa said seductively.
She grinned evilly, and I started laughing harder now and leaned back in the bar stool.
"Now why would I say no," I asked trying to sound serious, "I would hang with you girls whether it was here, or on the other side of the world.
Even if there were no sex involved, I'd still enjoy your company."
"Awe," they both said in unison and reached over on both sides of me to give me a giant hug, "We enjoy your company too," Holly said giving me a peck on the cheek.
"So it's a deal," Lisa asked.
"Sounds good to me, I'll pick you girls up tomorrow around 11:00 or 12:00 if you want and we'll go spend the day together someplace. Maybe a movie or something like that... sound good?"
They both agreed, and the plans were made. I finished off my beer, said goodbye to them both and once again was on my way home with Rob and Annie giving me a lift.
I was definitely looking forward to tomorrow, whether Holly and Lisa did intend on having a threesome with me, or they just said that jokingly I did not know. It did not matter really though.
Sure, the idea of it turned me on, but I would love to hang with them both if we were having sex or just hanging out. Either way, I was certain tomorrow would be a lot of fun.
Good story! Wish I was Jay!
Amazing story, extremely well written and I got horny as fuck reading it.
Great stuff.......are we due for another installment this week? This is almost better then doing it!Quote:
Originally Posted by SW91
Thanks for your time
You're just stealing this guy's work you loser:
https://www.literotica.com/stories/m...ge=submissions
Thanks HerrGunderson .Quote:
Originally Posted by HerrGunderson
Wow, hell of a story. Well done!
nice one!
great