by Twisted and Lovin It

Gender: Male
Age: 43
Race/ethnicity: White
Location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Pot Farmer
Relationship status: Married
Religious affiliation: none
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? Hundreds and hundreds I don’t really know.
How many hookup stories have you here posted before? 0

Jumping the Fence

How long ago did this hookup happen? 5 years

How would you best classify this hookup? One Night Stand

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Very pretty, Transsexual male to female, shorter with long black hair. I had only the slightest idea that she was a male. I had no feelings before because I had not met her before. But when I saw her I wanted her and had very strong sexual feelings for her. I was at a bar and she approached me at the bar. She was very provocative and I was more than willing to touch and show my affection back toward her. I have never been shy about showing that I want to have sex. I don’t beat around the bush I let the women I meet that I want to fool around and if they don’t continue to come on to me and let me in then I usually move along pretty fast to the next person so I don’t waste time. I am usually out to meet and fuck.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in a bar looking around and taking in all the pretty people when she approached me. We had the normal small talk but she let me know that she was also interested by touching me on my leg and back and doing all the slutty flirty things that I love women to do. We also talked and I acknowledged that I knew she was a transsexual. I did not care and it was very hot how we were acting. I would say that it was both of us who wanted to hookup.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We were grabbing each others ass and kissing at the bar and then we just took it to the next level by her asking me to go with her to her house. I did not waste any time and we went right away. I had played around a little with men but not really. Only them giving me a blowjob or me doing anal to them but I have not really done a lot with men. I am straight but am willing to jump the fence if I know that I am going to get off and not have to do anything to the man. Selfish I know but such is life. Anyway, it was very much a traditional situation where I was the dominant male and she was the ever willing non dominant woman. We kissed and touched and then we got naked. She started sucking my dick and would stand up and face me while we kissed. She also had very nice breasts which were large and did not look fake. So I would kiss and suck on those while at the same time taking her penis in my hand. I did not even care that I just went down on her and started sucking her dick and it was the first time i ever did that. She said I was good at it whatever that meant. I just did it like I thought I liked it done to me and it was great. She then sucked me off some more and turned me around and started licking my ass from behind and then my taint and balls all from behind me. I thought she was going to fuck me but she did not. She laid me down and sucked me off some more before getting on top of me and putting my dick in her ass. It was as good as I knew it would be. I have had a lot of anal with women and several times with men and I really do enjoy and love anal and this was no different but it was totally hot. I was really loving it and she was too. We did not care at all that we had just met and that we really did not even know each others name. Just hot fun sex between two adults. However she was about half of my age which to me made it much more hot. I love hooking up with younger girls at my age because I love being able to make them have pleasure from an older dude when they most likely would not choose me. However after sex with me I usually change them. I am a sex master and really have made many women sad that I only want a one time deal with them as most of them fall madly in love with me after sex. I can go a long time without cumming so this was no different. We changed positions a few times before I mounted her missionary style for my final thrusts. I started jacking her off as i was fucking her and she came pretty hard and while she was cumming and her ass was tightening up from the convulsions she was having I also came inside her without the use of a condom. Stupid I know but sometimes it happens. She also did not say no. She asked if I wanted to stay the night but I did not. I usually don’t want to stay more than a minute after I cum and I put on my clothes gave her a hug and walked out into the San Francisco night with a smile and a chip on my shoulder looking for another hook up because it was still early.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not talk about it at all and we did not care it was just hot animal sex and all we wanted to do was fuck and cum.

What were your REASONS for having this hookup? I love sex and look for it almost all the time. I want it every day and usually can find someone if I really want it.

Were alcohol or drugs involved? If so, how much? We both had a few drinks and I also smoke Marijuana almost every day so I am sure I was smoking it then.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? If I saw her again and she wanted to fuck I would totally go with her again. I love hooking up and never regret it. The worst piece of ass I ever had was wonderful.

To whom did you talk about the hookup? How did they react? I don’t usually talk about my hook up with transsexuals or men with my friends. I usually don’t talk about any sexual stuff with friends. I just rack them up for my own experiences. I love it.

Was this a consensual and/or wanted experience for you? For your partner? Yes we both wanted this and we both got what we wanted.

Do you regret this hookup? If so, why? I have never regretted a hookup. I don’t regret this one. Sometimes I do want to go back and do it again but more than one time and most people expect you to start dating and really l love women more than men in regards to sex so I did not even think about trying to be with that person. It was just a great sexual experience.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was pinning her down missionary style and cumming in her ass it is a huge show of dominance and I love that part of it. I am in control of the other person totally at that moment. The worst part is that I get up and leave out the door and I want a woman because I still love pussy and need that too so if I did not get it I go right back out and find a woman to fuck. Experiences with men always open my mind up a little more to accepting people as they are. We are all sexual beings and we just need to act more on our sexual feelings.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? I am empty inside until I know that I am going to have sex with the person I am trying to have sex with. There comes a point in the conversation that you know it is going to happen or not. When I get that feeling I start these feelings inside me that I can not control and it overwhelms me. I will put aside everything just for the sexual release of cumming. Afterward I feel great and ready to take on the world. I only feel bad when I know that the other person would usually like more but I do not. It is easy to manipulate the situation after that to use the other person and I do use them often as I am pretty fucked up in the head but I am a master lover. So like all good artist I just keep crafting my art and move along in life. I have said many times and have found it to be true 99% of the time that if you have sex with me it will change your life and you will fall in love with me. But I will leave you and you can not change me.

You have a hookup story to share? Submit it here!