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I am in my 50's now, and have had plenty of women of all sizes, shapes, and from decent looking to outrageously beautiful. I've even had my share of men, and a couple of trannies as well (I'm very partial to fucking asses, female preferably - but any port in a storm). I am a leg/ass man, always have been, prefer darker haired women, black hair is the best. However; I can't stop thinking about an old girlfriend in college. She was doing her Masters program and was quite a bit older than me, 6 years. She graduated, taught for 4 years, then came back for her MA. We talked a lot after classes, hung out a bit and for some reason I was asking her out. She a dark brown haired brunette, good looking and had incredible legs, and a nice bubble ass. I was already hooked on ass fucking by then, but figured we'd better go slow. Then at dinner one night she announces that she is still a virgin. I can't believe that there are any 27 year old virgins anywhere, much less in a college, in a mid sized city. So I went slow, we started kissing and making out, she had a great body but was a little light in the tit department. She had full A cups at best. My two girlfriends (that I had together in those days) were both A cups, my main girl not even a full A, so I didn't care. I was kissing her, had her pants off, her panties down and was fingering her super bushy, thick thick haired pussy, I still to this day haven't seen a girl with that thick a batch of hair on her pussy. She kept not letting me move my hand up her blouse, so I kept it outside her blouse when squeezing her tits. I figured I was fingering a virgin pussy, eating a virgin pussy - I finally while eating her got to see her hymen, and was even fingering her asshole which was incredibly tight, and I'd have some virgin ass before. Eventually I get her to agree, and we go to a motel I turn off the lights at her request, and at my insistence I leave the TV on for some light as I wanted to see her face when I plunged my cock into her pussy and break that hymen. I get her bottoms off, then her blouse, and you can tell that she wants to keep the bra on, and I just reach over and pull it up over her tits. Except there were no tits. NONE. She was flatter than I was, she was like 12 year old boy flat. All she had was nickel size brown areolae and pencil eraser nipples on a totally flat chest.
I took off her bra and the tissue in it, and laid her down. Seeing that forest of pussy hair, I plunged in and took her cherry. She bled a little, gasped a bit, then put up with my pumping her until I shot my load without a rubber on at all. We fucked for about a year, she got very relaxed about her lack of tits with me, and didn't care anymore, I could suck them tweak them do anything to any part of her. Once in a car I was getting a suck from her and told her I needed to come and she wouldn't let up, so I shot in her mouth. She said I was the first she'd ever sucked, but I figure she was lying. To last 27 years without getting your pussy popped she had to be giving her dates something. Then another time in a car again I had her pants down and went to fuck her from behind. I was fucking her and went to rub her clit and realized I'd just taken her asshole. I was fucking her in the ass and she never said a word, then I inserted my finger in her cunt and moved both around till I shot my load up her asshole.
So after that I had a three hole bitch, with no tits, who felt grateful that I wasn't that into big tits. We kept up fucking for a while, then I left school (I was done, she was still playing around) and I went to work and traveled a lot. I hadn't seen her for over 6 months, only called her three time or so, and one of those made her get me off on the phone. I went to the university and we talked, she realized it was over. She married an older grad student, who was pretty darn fat, but I guess he liked anyone who would let him fuck her.
For some reason for the last couple of years, I'm super attracted to titless women, and can't help thinking about her. That totally flat chest and that super thick bush still stick in my mind. I've wanted to go to the small town she lives in and taught in, just to see if I can see her again. But I know better, what you see after this many years never turns out well.
I feel different now. It’s hard to explain but I’m 20 years old. I broke up with my ex a few weeks ago. We were together for 2 years and she was my first and only when it comes to sexual stuff. She’s very pretty but thin. I thought it was great until this last weekend. This girl that just started going to my gym came on to me at 1am when I was working out. She’s like 30 years old, not the best looking face but pretty good sized boobs but an amazing lower half. Thick thighs and a big butt. I wasn’t attracted to her personality but sexually I’ll admit I was into her. She told me she was looking for a casual partner. We slept together once and I couldn’t believe how good it felt. I never felt curves before. Just feeling a different body in bed was amazing but to feel all her thickness. I feel addicted. I feel guilty as well because I do still love and want my ex back. But I don’t know how I can go back to being sexually attracted to my ex when this girl made me finish twice in the same hour.
We were off the main flow of the party and just chatting. Then I started flirting and he was flirting. Not sure how or who started it. This was my dads friend who was complimenting me. And a little touching as he tickled me. It was fun, exciting, and arousing all at the same time. Then he kissed me. As I pushed off, he started rubbing my crotch. Now I was wanting and allowing him to kiss and touch me. Next his hand is down my pants. And am feeling emboldened, so I rubbed his pants. On the outside, his dick felt thick and hard. I didn't have the courage to reach down his pants and verify it it was really that big. We remained fully dressed except my shirt he had unbuttoned enough to expose my braless tits. The perfect ones he said he had always adored in so many ways. One hand was on my tits as he licked and sucked. His other was fingering my pussy making it noisy and slushy. This was the best sex I ever had. I was biting my lip trying to keep quiet. As soon as I was about to come, we heard someone approaching. We quickly broke off and parted. He returned to the party and I went to my room. For at least an hour that night I fantasized and masturbated having multiple orgasms.
Now he wants more and I tell him it was a mistake. I said in case you didn't know, I am only 16, a virgin, and I don't act that way. And that he should just consider himself lucky to catch me at that time and place. But now we must move on and pretend it never happened.
If he's around for my 18th birthday party, I want to pickup where we left off. He's very attractive and obviously turns me on.
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I'm in talks with a ftm pornstar. We are planning on him fucking me in the ass. He chose me because of how thick I am. Not really a confession more bragging.
My roommate knew I was stressed so he asked me if he could do anything to take the load off my shoulders. I told him if he released his load in my butt I'd feel much better.
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