Lost my anal cherry

[TimCarpenter]

The girl is a friend of mine, well more of a former co worker who I keep in touch with for the past 2 yrs. Hot blonde about 5'7 120, tight ass, athletic, fake D cup breasts. She used to joke around with me and tell me she liked to fuck guys in the ass with a strapon and its how she got off. She liked to be dominant over a guy and be the boss. I didnt know what to think of her, most of our friends thought she was a lesbian and we had never seen her intimate with guys or girls. She was a big question mark and it turned me on.

I always laughed it off and thought she was joking or just talking a good game. Well long story short, we were having some drinks last night at a local bar and as she got more intoxicated she kept saying what a nice ass I had, etc. I had a few drinks of my own and started to smack talk back with her. After about an hour she invites me over to her place so I leave with her. Let me tell you, she was NOT joking or playing games. From the time we got into her place it was go time. She pushed me against the wall and immediately dropped down and started sucking my cock as I played with her fake tits. She led me over to the couch and straddled me riding my dick until I came inside her. ( I regret not wearing a condom but it all happened so fast and the alcohol clouded my judgement)

Now she said it was her turn to fuck me. My heart was in my throat, i got nervous because I knew this girl was not playing. I was scared but wanted it at the same time. She goes into her closet and pulls out a box of sex toys. This was obviously not her first rodeo! She pulls out a mid size strap on as I tell her it was my first time. Im judging it was bout 6 inches in length and average thickness. She pushes me back on the bed and straddled my face making me lick her pussy (which I just came in by the way). She eventually cums all over my face as eating pussy is one of my best skills. It was so wet I couldnt tell if it was her cum or mine but at this point I didnt give a shit. Then she turns facing my ankles and spreads her ass telling me she wants to lick it clean. I didnt go this far to stop now so she basically smothers me and I lick her asshole for about 5-10 minutes and just get lost in the moment. I had no problem with this because I have a big time ass fetish and she has a tight bubbly butt.

Next thing I know she breaks out lube and has me lie face down. She lubes up her tool and my ass with her fingers. She was very good at loosening me up with her fingers for about 10 minutes and just helping me relax. I am twice this girls size but she is the boss now and i am pretty much powerless. Luckily for me I was pretty relaxed from the alcohol and didnt tense up much when she inserted the cock. It was the weirdest feeling in the world with her fake tits agaisnt my back and her hips pushing into my cheeks. I was getting owned by a hot chick. I felt vunerable and weak. She went super slow and really opened me up. I had a weird feeling like I had to poop but I didnt. My dick which was hard also went semi soft. It was a strange feeling. Hard to describe if you havent done it. We were literally in this position for about 15 minutes until she picked up the pace a bit and added more lube. She was talking dirty to me the whole time calling me her slut and asking me what it felt like to be dominated by her hard dick. She told me it was her ass now and I could only have it back when she was through with it. She alternated between pushing the back of my head into the pillow and wrapping her hand around my throat and mouth.

We kind of role played the whole time this was happening. She made me answer questions like "Who's ass is this?" and "Who's slut are you?". She basically pinned my calves down on the bed with her instep/shins and flattened me out. All of the sudden my dick started getting more erect again.

Eventually we switched positions and she put me on my back and lifted my legs up. She placed a pillow under my ass to raise me up a bit to make entry easier. I found it much easier to take her strapon from the missionary position (not sure why). There was something about her looking into my eyes while she was fucking me that made me hard as hell. She had sexy brown/hazel eyes. Her fake tits where in my view now also which was hot as hell. She used her hand on me from this position also. Literally within about 7 minutes of putting me on my back I spurted a weak load immediately followed by a blast that literally almost hit me in the face. I have never had a multiple orgasm before but this had to be one. I had an orgasm feeling with a small amt of fluid released then like a 2 second pause then a big eruption that could have taken someones eye out literally.

After it was over, we cleaned up and just hung out and had another drink at her place. It was not weird at all. I felt strange but she did a great job of making me feel normal. I was almost in a trance state where i kept thinking "i cannot believe this just happened" It was a fantasy of mine for quite some time but making it a reality was a whole different ballgame. When I finally went home to go to bed she said we should hang out again sometime and I totally agreed.

This was the best yet strangest sexual experience of my life. I loved the feeling of her cock inside me but even more so I loved the fact she was so feminine and sexy body with big tits. I can only imagine how much better it would be with a shemale/ts with a real dick who's hard cock I could make orgasm. This was my first experience and i am hooked. I think I will be seeing her again on a regular basis until I complete my next fantasy of a real life sexy shemale.

On a side note one thing I can say is when you dont tense up and actually relax you can fully enjoy the experience. My ass is very sore today as this was my first time, almost a burny feeling but I can say it was definitely worth it. I still can't believe I finally went through with it.

[zerokool]

Congratulations. Let's just hope you didn't get her pregnant.

[TimCarpenter]

She is on birth control, I was more regretting the situation because of the chance of STD but I am planning on getting tested again soon.

[Rusty Eldora]

It takes a while for results to show up, I recall 6 weeks min for HIV to be found in a test. If you are going to be playing regularly with her (why not?) it may be good for both of you to test.

About 2 months prior to my first TS, I experienced a strap on, the real thing was much better. It felt quite amazing.

Have fun

[Westheangelino]

You've got nothing to worry about as far as HIV is concerned. However, you might develop a bad hemmoroid or two

[Dino Velvet]

However, you might develop a bad hemmoroid or two

Just call Raymond then...

[giovanni_hotel]

I think this is what they call consensual rape.

[TimCarpenter]

Thanks for the replies friends!

[TimCarpenter]

I am planning on losing my "real" virginity with a ts while visiting Vegas. Does anyone have suggestions for me on who I should see that is good with first timers. Karen Cummings sounds great but there is no way I could "accomadate" her. How about Alexxa Gray or Brooke Bangs? They seem to stand out to me!

[Dino Velvet]

Is Foxxy around? She's got a good rep.