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  #1  
Old 12-26-2012
TimCarpenter TimCarpenter is offline
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Default Had my first bottom experience last night

Last night with a girl and a strap on. 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.
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  #2  
Old 12-27-2012
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Default Congrats

Sounds fun!!
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Old 12-28-2012
TimCarpenter TimCarpenter is offline
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It was intense! Cant wait for round 2 or to find a real girl with a beautiful cock!
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Old 12-31-2012
testbed testbed is offline
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Congratulations, but a real cock is far better than a dildo.
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Old 01-02-2013
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Florian Florian is offline
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Sounds like you were (almost) made for each other. You obviously don't like the "fake" in "fake tits", but who knows how this is going to develop? she seems to have everything you need.
Thanks for telling us - one of the most erotic experiences I've ever read. Don't lose her number!
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Old 01-02-2013
TimCarpenter TimCarpenter is offline
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Quote:
Originally Posted by Florian View Post
Sounds like you were (almost) made for each other. You obviously don't like the "fake" in "fake tits", but who knows how this is going to develop? she seems to have everything you need.
Thanks for telling us - one of the most erotic experiences I've ever read. Don't lose her number!


It really was erotic and intense. I was totally lost in the moment than after kept asking myself "did that really just happen!?" haha. Not too get too graphic but my bottom was sore enough to let me know it did just happen! haha
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Old 01-07-2013
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Quote:
Originally Posted by TimCarpenter View Post
It really was erotic and intense. I was totally lost in the moment than after kept asking myself "did that really just happen!?" haha. Not too get too graphic but my bottom was sore enough to let me know it did just happen! haha
I've always found it weird, but being in a little pain after sex just makes the memory more intense. I don't mean serious S&M, just if my balls ache half the day I know I've done my job.
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Old 01-07-2013
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Default You Go Boy!

Congrats! The second-best sex ever, right? Just wait until you get 'the real thing', that's number one! Oh so beautiful, a nice stiff one up the bum hun!
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Old 02-02-2013
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georgedemesa georgedemesa is offline
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My girlfriend tongue fuck my ass and i ilove it but never tried a strap on .nothing beats a real ladyboy cock
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Old 02-02-2013
londonkangaroo londonkangaroo is offline
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Well done ! Next time try a real she-cock. Nothing turn me more on than my tgirlfriend's cock splashing her sperm in my ass. Jerking off when being fucked is wicked !
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Old 02-20-2013
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Had my first experience 2 days ago. I'm in the middle of farm country in northern Japan, so there are little to no T-girls in the area. I decided a pro would be the best option and found a place online that was about 200 miles away. Ended up taking a bullet train to get there. Upon arrival, I called the establishment and was directed to an apartment in a multi-story building.

The girl that greeted me at the door was one whom I immediately recognized from the photos in their online 'line-up'...and that only increased my excitement level! I was shown a catalogue of the available girls, some with balls and some castrated. The gal made sure she was clear about who had balls and who didn't. I chose a compact, cute, but fully equipped model. By that point, I was nearly trembling with excitement. I chose the 'Premium' package, which include 'AF' (anal fuck, you deliver) and 'Gyaku AF' (She delivers).

I was led to a room, told to have seat and that the girl would arrive shortly. About a minute later, I heard a knock at the door and in came a perky little gal with about a 'D' cup and nice ass. She told me to disrobe while she took a shower and changed. When she came back to the room she saw my 'fun meter' was alread halfway pegged, but I had to wait, it was my turn for a shower.

I was led to the bathroom where I showered and brused my teeth. When I finished, the girl dried me off then led me back to the room. We sat down on the bed and commenced to kissing, followed by mild foreply then engadged in a 69. She asked all of the right questions and found out it was my first time receiving anal sex. She went to work on me like, yes, a pro.

First, she pulled out 3 sizes of penis-shaped sexual toys ranging from very small to one that was a hair smaller than what she was hung with. As she progressively inserted each size, I was wondering if the real thing would feel the same (sensation of taking an uncommanded crap when pulling out!). While she had the largest one in, she turned the vibes on, which gave me a very small hint that things would change for the better. Little did I know HOW MUCH better!

We chose missionary style. She rolled on a condom and applied generous amounts lube to my ass and her cock. As she started to slip it in, I felt a wonderful warmth radiating from her cock that simply wasn't present in the sex toys. Even better, I felt no pain at all. She worked her way in until she reached the hilt, asking me how I felt the whole way in. I felt great! Once she started the stroking action, things went from great, to 10X better! I started breathing heavily with a warm sensation all over my body and a mild sweat. That's about all I can put into words because the rest was indescribably awesome! I came close to shooting a hands-free load several times. Then it was my turn to give. I took her in a variety of positions, finally shooting my load into her (with condom) doggie style.

This was not a thrifty excursion, but I definitely will be back. The trip was worth it because, as pleasurable as the anal sex was, having a dude on the delivering end would totally kill it for me. I never understood how receiving anal sex could feel so good, but now I totally understand, and can empathize with gay men in that respect.

Last edited by Transation; 02-20-2013 at 04:28 AM.
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Old 03-05-2013
sebation13901 sebation13901 is offline
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That story sounds freakin awesome. I have never given or received anal but I want to for sure.
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