A Night with a Sexy Shemale

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down so I am a new man this is about the man I was before I matured and settled down.

After I got out of the Army I kind of stayed at a motel in Georgia to unwind after a long time in the Army basically waiting to start my college time but in the meantime I didn't see why I shouldn't explore my sexuality the first thing I wanted was to get to know some women that I could kind of get to know maybe fool around with I never intended to be with a lot of women because I do have a lot more respect for the female species than some of my male brothers.

Well for some reason at one point or another after I had my first blowjob from a guy and after that started having regular sex with a local girl that was three years my senior and a teacher at the local elementary school we had a very open relationship it was the perfect situation for a twenty three year old man. I wanted to know what the experience of being with a man or with a shemale would be like so I started to join dating sites for gay men but I made sure they all knew I was labelled as Bi Curious I had to be open and upfront because I didn't want any person I would meet to think I was interested in a relationship when I was in no way shape or form familiar with my sexuality or if I could even perform with a shemale or a gay male.

I seemed to always hit a brick wall when it came to meeting gay males they seemed to live too far away or would be only interested in me if I was a confirmed gay male I was not really even sure what I would do if I was with a gay male I had an older guy offer me his bottom but he lived all the way in Florida I did consider it a possibility but for some reason every time I thought about it, it just made me uncomfortable so I decided because of that I need a shemale or crossdresser so I started watching the porn to see if it excited me and it absolutely did and I enjoyed the thought of a male dressed up like a woman being fucked by my cock and moaning like a woman.

One night like somebody upstairs was reading my mind I get a knock on the door I look through the peephole it was a black woman very tall but attractive. I opened the door with my boxers on to see if she was interested or just looking for directions in any case she looked straight at my crotch and invited herself in and so she sat down I sat on the bed she wanted a cigarette and I gave it to her she introduced herself I can't quite remember what her name was but she was definitely turned on by this and so was I she told me about herself she kept looking at me and looking at my crotch. She said she could really use some extra money for gas to get home if I could spare some this was in no way shape or form a transaction.

When I gave her some tiny amounts of money she looked at me with a smile and said "let me taste that cock" I immediately pulled down my boxers out sprang my white cock she took it in and started devouring it and moaning as she sucked it like an expert. She stopped and said we have all night darling why don't you suck my tits so I did I kissed at them flicked her nipple with my tongue she moaned and grabbed my chin kissed me on the lips pulled her tongue in my mouth massaged the tip of my tongue with hers. At this point I honestly thought she was a woman until I felt her crotch and found a big cock! I felt it and rubbed it I didn't know what to do I just kept going kissed her neck and just sat there as she talked to me and then after maybe an hour she asked me what I would like to do next I told her shyly well I have been wanting to explore my sexuality I asked could I suck your cock.

I couldn't believe these were my own words I am a straight man and I just asked a post op shemale to suck her cock so she got on the bed she laid there revealing her giant cock I took it in my hand and stroked it like I knew I liked and she moaned I knew exactly what she liked because I had a few blowjobs that I enjoyed I started to suck her cock she really started to enjoy it putting her hand to my head as I sucked away like any woman I was with or any woman I had watched on porn. I knew I am straight I didn't know how to tell her I wasn't interested in going any further because it wasn't in me but I was appreciative as she was appreciative of the pleasure I had given her. So she started to jerk herself on the bed while she sucked my cock and she released her cum on her thigh I gave her a napkin to clean herself she kissed me and said thank you that was great baby,

Then she asked me to do something else for her she asked me to spit on her asshole so I did and then she rubbed it working herself over she looked at me smiling ok baby I want you to fuck me hard and cum inside me. I positioned myself behind her but I went limp and I told her I had a problem she worked with me she laid me on the edge of the bed and had the chair pulled up so she could work on my dick and get it hard again she just sucked my dick like it was never sucked before she went to town she enjoyed my cock very much. Then when it was hard a sloppy with her spit she turned around and put it in her ass worked it in slowly next thing I know she is riding my cock while jerking herself off. I could not believe I was watching my own cock go into her ass and it felt just like a pussy, I then told her to lean over so I fucked her doggystyle from behind she yelled in pleasure fuck me with the white cock cum in my pussy.

I fucked her like I did any woman and it was fun I was with her only a few more times but that was the only time I sucked her and fucked her the other times she just sucked my cock, and we talked she even wanted to get into a relationship with me as hot as that sounded I knew I could not do that it wouldn't be right at this time I knew I am straight and not bi sexual and definitely not gay but I can understand why they enjoy it and in as much I have a story to tell them that they may enjoy. Last time I saw her I kissed her good bye not realizing I was kissing a man it just seemed natural at the point it made me understand something that people are people and no matter what is between their legs we can feel intimate toward anybody all we have to do is let ourselves welcome them.