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Awkward Moments in Porn 14

Awkward Moments in Porn 14

Accidental Cum Shot

Accidental Cum Shot

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The Adorablest Camwhore

Prostitute Lasts Only 28 Seconds

Prostitute Lasts Only 28 Seconds

HARDER! Or I Cant Cum!

HARDER! Or I Cant Cum!

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5
Anonymous
@confessions
11 Aug 2015 2:33PM
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Finally had my first experience with a transexual woman (pre-op.) It's been a long time fantasy of mine, and I just decided it was time. Went on to backpage, and found a prostitute. Yeah, yeah I know, lame but believe me I've tried the old fashioned way, I'm a big guy, and in my experience transexual women tend to be more picky than natural born women. So I paid (sadly I had to pay more BECAUSE I'm a big guy, but no reason to get cold dick just because of another obstacle)

She was Asian, very passable, with and once I got to her place she was fairly understanding, and pleasant. We started slow since it was my first time, and kind of let her take the lead. She asked if I was comfortable with her taking off her bottoms, (I assumed that's what she assumed I was there for but I guess some guys are conflicted) and I might have betrayed my eagerness a little bit because once her cock was out it went straight into my mouth. I asked her to teach me what she liked, and that seemed to be her specialty because she made sure I didn't miss an inch. I've never been what you'd call submissive, but letting her take control was very freeing.

I think she noticed I responded well to that, so she didn't ask me to eat her ass, she just turned around and grabbed my hair. It was so clean back there, and she smelled nice I had no problems. Once she was tired of that, she sucked me off (intense!) and rode me until my soul came out.

I asked if it were possible that she could come for me, and she made me service her ass again while she jerked off. She told me she was coming and I caught it all. I understand now why women want to kiss after swallowing, but she wasn't too into that.

It was cool, and fun, and I definitely want to do it again. Maybe when I get my Christmas bonus XD

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Anonymous
@confessions
04 Oct 2011 12:03AM
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While some would consider this a confession, confession implies that I feel guilt about the subject. I feel no guilt, to me it is a fond memory that some will enjoy, I'm simply sharing.
In 1985, I was stationed in Korea, due to family assets and my paygrade, I was quite well supplied with funds. This was before the "Korean Economic miracle". Pretty much anything was available in Korea for a price. I had the price. I had become somewhat bored with the usual diversions available in the "ville", and decided to find something different. I roamed the bars and clubs for the unusual. had some interesting adventures, yet still hadn't quite found that "something special". However my search bore fruit, I realised one of the Korean bargirls wasn't quite what she seemed. Now this girl was quite lovely, and well known for never having actual sex with guys that picked her up. Her customers were usually young, drunk and horny, and she satisfied them orally. To put it bluntly, Miss Kim could suck the crome off a trailer hitch ball. Now I bided my time until the Team Spirit exercise was well underway, My unit was exempt from exercise activities, I took leave for the 10 days or so of Team Spirit and happily relaxed in my off base quarters. The "ville" was quite pleasant, not many troops running the bars, and the bargirls had cash flow problems, most paid their rent on a weekly basis, and with few customers they were having trouble making the rent.
Miss Kim was no exception. so one night I bought her several overpriced "juicies" and started negotiations. She quickly explained that she only did blowjobs, no sex, we agreed on $15.00 the going rate. Then I brought up the subject of extras. I am quite fond of bondage, nothing rough or painful, just bondage. She seemed less than thrilled, but rent was coming due. We went to my apartment, it was a cold night and she was quite happy about my budget allowing more heat than she could afford, We actually had a snack, she was rather shocked when I cooked a couple nice omeletes, apparently Korean men know there is a kitchen in their home, they just don't care where it is. Miss Kim stripped to the waist, nice breasts, small, but then Asian women aren't noted for having huge breasts. I tied her hands behind her, she knelt and nuzzled at my jeans, Then I surprised her, she wasn't expecting that I would tie her ankles and then connect them to her wrists. I rubbed her neck awhile, she relaxed, Then I really upset her, I pulled her jeans down, sure enough, there was a penis, She was a pre-op transexual. Kim was quietly freaking out now, but I rubbed her neck some more. Finally she nervously asked what I was going to do, I happily explained I wasn't going to hurt her, but I was going to get the blowjob I paid for and was going to take some pictures. I promised no one else would see the pictures, and her penis would be our little secret. We both knew that in Korean culture she would be outcast and fired at the very least if the club owners knew she was a pre-op. So she knew I had her right where I wanted her. It was an excellent blowjob, probably the best I've had. When she finished she asked when I was going to untie her, I said in the morning, I had been watching and while blowing me, Kim had become very erect, not a large penis, rather small actually, but quite erect. I asked what she intended to do with her hard-on, She wanted to masturbate and couldn't with bound hands. I had a perfect situation, a lovely "girl" bound and desperate for sexual release, and quite helpless. She tried to rub herself on the sheets, but I wouldn't allow it. I embraced her and explained that she needed to make me very happy that night, and that I might help her out if in a good mood. I think being revealed as a pre-op and being helpless combined to excite her. Her penis started twitching she was so excited, so I offered my cock to her lips again and I thought she would suck my balls through my uretha. I pulled out and shot a load all over her face. She was so excited she was trembling, being a nice guy in my own way, I took her penis and started slowly stroking her, she shot off in about 30 seconds. I offered her my semen covered hand and she licked it clean. I cut the cord attaching her ankles to her wrists but left her bound, we cuddled and rested awhile. Before long, she started licking me again, she was as aggressive as a bound person could be. We had a nice long talk on many topics, including anal sex, Kim was an anal virgin. and quite scared about anal, I told her I would never force anal on her, but with vibes and such we could prepare her for anal. Somewhere in the course of the night we agreed that she would quit the club job and move in with me, I had about two years left in country. There was a financial part to the arrangement of course, I had a very agreeable sex slave for about two years, and she had a nice little nest egg to pay for her operation. Now this was before don't ask don't tell, and of course we were very discret about her something extra, Kim was usually bound during sex, she seemed to enjoy being helpless, but safe, In fact sometimes I would get home and find she had cuffed herself and was kneeling in the living room. I was always careful to not bring friends and co-workers home unless she knew in advance. Now both of us are married to others now. I to my wife, who knows nothing of this period of my past, and Kim to a nice Korean man, who knows she wasn't born female. Other than Christmas cards we have no current contact, my wife thinks Kim was my secretary while I was in Korea. Upon reflection, I think I was attracted to Kim because I knew I could have a submissive lover, her penis never really interested me, other than a means of control. But considering that I do have a somewhat nice Motherless.com gallery of TG's I have to wonder. Just thought I would share this little story.

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