What was your best / first time with a shemale like?

[colin3831]

I'm guessing that like most people who have ever been with a shemale, you don't tell any of your mates about; so why share the details of your first time(s) with this site - the more details the better!


My first time was with a dark haired escort, I phoned and had her to come to my place. She was South American, slim build, nice face and breasts, cute accent. I was really nervous and not sure what I wanted or what was safe, I had all sorts of thoughts running though my mind, anyway, I ended up asking her to do a striptease for me. I thought at least I could get to see a shemale for real, after a while she got down to her birthday suit and holding her tool. She waved it in my face, laughing, saying did I want to suck it, part of me did, (in fact part of me just wanted to bury my face on the end of it) but I just did not know what to do, so I said 'no' and asked her to wank off, which she did standing in front of me, she left a pool of cum on my wooden floor for me to clean up later.

The one good thing about this rather poor performance on my part was that it got me over my doubts, 'what will happen', 'will I be able to stop it', 'does it mean I’m gay if i suck cock', and worse of all ‘What if she tries to fuck me, am i prepared to be a bottom', etc. A week later I called the same girl, as she came in I could she her smiling and straight away she asked if I was now ready for more; so I just said yes and we both stripped got onto the bed. We played with each other for a while, I was mainly fondling and kissing her breast, I was still unsure about heading south but slipped my hand down there and started to play with it, she soon got hard, it was smooth and wet, but was quite small maybe 6 or 7 inches, it felt good to finally hold/touch a TS cock. She turned the pace up notch by turning round and going down on me, this left her cock in front of my face, it was uncovered but by this point I did not even think about it, I just put my head forward and sucked, it felt strange to have a cock in my mouth and I could feel it hit the back of my mouth as she pumped forward - face fucking me. After years of wondering what it would be like it was good to finally be doing for real.
After a while it was clear she wanted to do more, she had been steadily using one finger and then two up my arse as she was sucking away on my cock, which was more of a turn-on than I could possibly imagine. I thought that I may as well find out now, so I allowed her to slowly pull my legs up and over my shoulders as I lay on my back, she covered up and pushed forward, as I watched her slip into me, I had expected it to hurt but it was ok, she pumped away for a while and then came as she was pulling out. Having just been fucked up the arise for the first time in my life I was somewhat unsure what to feel but one thing I was sure of, was that I wanted to fuck her back, partly because I was horny, but also because I wanted to be ‘even’, now, I know its stupid but I did not want her to leave feeling I had been her bitch. So I pulled the duet off the bed and put it over a nearby table which was a just the right height, and asked her to bend over, she bent over face down, leaving her arse in the air, she said to go slowly as she had, At first I did, but then as I got more and more into it I went faster and deeper, I’m by no means superman but I am quite larger and thick and the thought / sight of her being fucked up the arse by me and her whole body slapping up against the table with every stroke I took was such a turn-on, I just could not hold back and fucked her arse for all I was worth. After a while I shot my load inside her, covered, and collapsed on her back panting and moaning.
She left shortly afterward looking slightly dazed and confused, as if to say what happened to the quite shy guy I met last time, I can’t say I blame her!

Overall it was a good time and although I normally go for girls, every once in a while I still find a stiff shemale to have some fun with.

:roll:

[colin3831]

Just to get going on this tread, my second time! (again not the real pic, but same type)

My first time with an escort in the red light district, anyway, I was looking in the windows during the day when I saw this girl, she was Arabic, tall and stunning, soft like brown skin, and dark eyes. When she noticed me eyeing her up and she smiled, I was not sure if she was or not, but then she briefly flashed her cock. So I thought, well its now the chance to try again, she was really cute and friendly, as I went into her room she asked me to sit down and offered me a beer, none of the real girls in the red light had done this. She chatted for a while and then asked me to strip and lay on the bed, which I did, she then proceeded to suck me uncovered. I moved my hand down and got a feel of her cock, it was completely soft and as I played with it it became hard and large, larger than mine! (maybe 8 or 9 inches). I could not wait to get it into my mouth and feel what it was like to suck it, so I moved off the bed leaving her half sitting on the side of the bed and me kneeling in front of her and put my mouth over the head, then started to suck it and tried to copy the movements she had used on me, she moved her hands to my head and guided me as to how she wanted me to suck, which was quite simply pushing it in as deeply as possible and then slowly pulling it out over my lips and face, as she looked down at me kneeling there between her legs with her cock in my mouth and her pre-cum on my face.

After a while she asked me to get back on the bed and told me she was going to play with me some more, she had me kneel on all fours, saying this would be the least painfully way to be entered (I had told her it was new at this). She played with my arse for a bit and then put a condom on, I was somewhat nervous about her size but she assured me it was fine, she would just go slowly. The wall to the side of the bed was a mirror so I could see what was going on, I saw her roll some spit out of her mouth and drop it on my arse to act as a lubricant. For some reason instead of being disgusted by this it turned me on to be treated in such a cheap way. (like I was some cheap slut who was about to be fucked for someone else pleasure/lust) She pushed forward and I could feel her head trying to get past my ring, it was painful, but I thought just hold on until its passed, once she is in it will be easier. After a few more goes she pushed the head in and I grasped, she paused for a moment while I got my breath, then she when on, pushing more and more of it into me. It was a relief when I could feel her balls up against my arse and knew there was no more to come. It was painful and uncomfortable but she worked away clearly enjoying herself, pumping my white virgin arse. After a while, she suggested I might prefer to sit on top of her, this way I could control how much was going up my arse, so we switched, she lay on her back and I sat on her, feeling beneath me for the cock and lining it up with my arse, as I guided it in, it felt completely different, I loved it, moving up and down and feeling it slide up and down my by now relaxed and wet arse.

She recommend that we finish with her on top (which was clearly where she liked to be, on top) and me laying on my back, we quickly switched, and just as quickly she had my legs up in the air and over my shoulders with her hands/arms behind my knees, (I knew this position from being with girls, this is when you are really turned on and intend to hold them steady whilst you do the final serious fucking).
She slipped into me and started to pump away, pushing deeper and harder all the time, then she changed pace and would slowly pull it out until the head was almost out and I could feel it going passed my ring, then in one quick movement she bang it all the way back in with a slap, she was (and I) was clearly getting more and more turned on, up until this point we had not kissed, but know as she came forward, holding me pinned to the bed, she would push her mouth down onto mine and french kiss, deliberately crudely covering me with her tongue. I was so turned on but also so shocked by the whole thing, and then right at the end she just went for it holding me down and fucking me. She came and then dropped down on top of me, I could still feel her cock inside me pumping away by itself, I pulled my arms out and put them around her and we lay there for a few minutes. She smiled and became softly spoken again, kissed my cheek and laughed that I was not an virgin arse anymore, I was laying there thinking you can say that again. I was sore, but without a doubt it was great sex.

[colin3831]

A few more great pics!!!!!!!!!!!!!

[colin3831]

even more great asian ts !!

[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[colin3831]

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[ricorusso]

I have to say that my most mind-blowing shemale experiences was one of the first. About three years ago when I first moved to New York I just decided that I would try one of the escorts in the back of the voice. I took a browse through and found one in Queens where I lived at the time.

I called and then took the train over there. She invited me in. She could tell I was very nervous. There was a king size white curtains sectioned off bed in the living room of her apartment. She escorted me to the bed and sat me down. She was very nice and beautiful in person. I have since seen her on Shemaleyum and a few other places.

Still in my coat and shaking she walked over the bed she gently spread my legs and nudged herself in between them. Her crotch moved inches from my face. I knew what to do and pulled her panties aside and let her chubby uncut cock fall out. I began sucking her as she moved from side to side up and down fucking my face.

She pushed me back on the bed and pulled my pants down. She was excited by and obviously surprised by the size of my cock. She started sucking me as she wiggled herself out of her panties. We had a really sweet fuck. Then when we were done I laid there naked. She got up and told me to relax. She offered my some juice and she disappeared into the kitchen. About that time I heard the bedroom door open. I could hear my girl and another talking loudly in Spanish and I could understand anything.

Next thing I know another girl peaks her head through the curtain. She sees me lying on the bed naked and walks into the room. Let me tell you she was fucking hot. She was wearing only a tight pair of gym shorts and a sports bra over her amazing tits. She was very dark Dominican girl. Imagine Eva Mendes with a dick. Anyway she comes over to the bed and sits down. It's obvious that she speaks no English. She starts talking to me in Spanish. I don't think I was able to respond I was too busy looking at her. I had never seen such a beautiful shemale in my life.

She moved in closer and grabs my cock. She started slapping it against her breast and then her face. I reached down to touch her tits and she smiled. Next thing I know we were in the middle of a long passionate kiss. Then suddenly she was taking off her bra and threw off her shorts. Her tiny little cock stood perfectly erect. She started sucking me and I was in heaven. Somehow she found a condom and threw it on me. Next thing I know she mounted herself atop my pulsing erection. She started grinding her ass on me. We kissed eachother so hungrily. All the while she speaking in Spanish and all I can hear is the word Poppy every few sentences.

He cock stayed erect the entire time. Finally she pushed her ass harder on me seemingly finding her spot. She started moving faster and faster until she blew a creamy load all over my belly. At the time I didn’t know that anyone could cum without touching themselves or being touched but she did.

She got up and ran into the bathroom like she was embarrassed. I got up and walked over to the bathroom and knocked on the door. A minute or so went by and she let me in. I threw her up against the bathroom wall and started kissing her some more. We were going at it then she said in her broken English “look” pointing to her cock which was erect again. I quickly bent down and started sucking her. We kissed some more and then we finally we got into the shower were we fooled around some more and she finally jerked me to orgasism.

I left that apartment a changed man. I had some other great experience with shemales but that day made me into a true lover. I never knew that I could have deep emotional love-making with a shemale the way I do with women until that day.

[LG]

Haven't been with many and haven't given or received anal yet- it's next on my list but I always chicken out at the last minute- afraid of catching something awful.

Two come into mind: One was one of my first- I received a blow job from a big black tranny until she complained her jaw was sore, so I asked to give her a blow job whilst I jerked off. I was shocked by the size of it- a good 7 1/2 or 8 inches of thick cock and I could only fit the tip in my mouth.

The best was also the most recent- a sweet looking ladyboy with a medium sized dick shaped like a banana. We 69ed each other on her bed. It was mindblowing, just laying there sucking each other for a good fifteen minutes until we both took our dicks in our hands and jerked until we came.

Since I don't live in a major city I can't seem to find any escorts. Honestly though, I'd rather meet a pretty t-girl I can care about. Then sex will actually mean something for both of us- I've never cared much for meaningless sex- call me a romantic. And then I'll no longer be afraid of cathing something. In fact, I'd love to give and receive both A and O bareback.

[colin3831]

Thanks for the great stories guys!

Here is a few pics you may like, your stories reminded me of a bj I also had from a black shemale.

It had been a while since doing anything real with a shemale, maybe a year, but had recently seen a few great pictures of well hung black shemales kept going through my mind. The idea of a cock that big, black, shinny, so i ended up looking one up on eros.com. She claimed to have ten inches and to be as stiff as a poker, i thought just the job. As few hours later I was nervously knocking on her door, when she came to the door she looked good, tall approx 6 foot, slim but not skinny and no attitude.

She quickly got her tool out, it was unbelievable, the biggest thickest cock I had ever seen. I told her i wanted to be topped, but she refused saying she would spilt me, but she suggested a 69. So we got down to the business both uncovered, her sucking me and me trying to suck her huge cock, all I could really do was lick her shaft and balls then suck on her wet head. She surprised me by rimming my hole, which was great and the first time for me, her rough tongue running around my arse hole felt great. It finished with me learning what it really means to be 'face-fucked', we both lay facing the same way, but with me half way down the bed, she lay on top off me, her cock right into my face and her strong black thighs either side of my head holding me down, whilst she would grind and pumped away at my face, getting faster and faster until with a moan and grunt it suddenly changed from a 'face-fuck' into a very wet and sloppy 'face-wash'.

A short but fun experience.

[colin3831]

anymore pictures of tops?

[Tanabata]

anymore pictures of tops?

[colin3831]

Do you have any more??

[dogwoodman]

colin3831 do you remember the shemale in NY.Her name and maybe phone number ?

[Hugh Jarrod]

anymore pictures of tops?


OK that's funny.

[Hugh Jarrod]

How did this turn into a picture thread. My first T was Susan Shah. The 1st to top me or take my virginity Vaniity.

[thehumanbehan]

Hugh Jarrod. Please tell us more about your experience with Vanity.
It sounds very interesting.