19biman61

When I was in my teens , in the 70's, I was as horny as any other male teen. I would jerk off to my older brother's porn magazines (some of them were hardcore). It was the hardcore mags that got me curious about having sex with men. Seeing women having sex got me instantly hard and me having sex with the single mother of two who lived next door helped to solidify my interest in women, but looking at the stiff cocks and the women getting fucked in their pussy and ass got me wondering what it would be like to get fucked and to suck a cock. Once in a while i would fake being sick so I could stay home from school. After everyone was gone I would dress in my mothers bra, panties, stockings and wig and jerk off!

After graduating from high school I spent four years in the army. During my time in the army I fucked a few women but didn't get into any serious relationships. With less than a year to go on my enlistment I would sometimes go to the local drive-in. They had three screens that were back to back in a triangle and you would drive around the perimeter until you got to the screen you wanted. One screen would sometimes have an x-rated movie showing. This one time the sign said the movie featured Sulka. I figured that Sulka must be someone special for her to be featured like that. I bought my ticket, drove to the appropriate screen, pulled out my dick and waited for Sulka to do her thing. When she appeared I figured that it was her by the kind of Asian facial features. She had a beautiful voluptuous body! Big tits, curvy body, ample ass and a big cock. I was not expecting the cock! I was mesmerized watching her! I shot my load three time while watching that movie!

I was soon out of the army and I moved back in with my parents until I got a job and saved enough money to get a place of my own. I would go to the local adult bookstore and go into the viewing booths to watch porn and jerk off. Sometimes it would be straight porn and other times it would be "tranny" or "shemale" porn as it was known as at that time. Most times while leaving the ABS I would look across the street at the lingere store and wonder what kind of good stuff they had in there. One night I went into the lingere store. I was the only customer at that time and I was greeted by a very pretty blonde woman named "Mandy". (not her real name) She was dressed in a white blouse, tan knee length skirt with pantyhose or stockings and white high heels. She asked me what I was interested in and I told her that I was more curious than anything. She smiled and said that she appreciated my honesty because most men that come in alone are simply curious but say that they are looking for something to get their girlfriend or wife. I told her that I was unattached and her smile got a little wider.

Mandy showed me the few things that they had for men. I decided to try on a pair of blue satin bikini briefs. As she was leading me to the dressing room she told me that the women's version were pink and that was the only difference. I stripped down and put on the underwear and they felt so good that I quickly had a raging hard-on. Mandy was just outside of the dressing room door telling me to "come on out so I can see how they look". I opened the door and stepped out. She told me to spin around and I did. She looked down at my crotch and said "they must feel really good". I know my face had to be red (I get embarrassed easily) and I said "yeah, they REALLY do". I got dressed, paid for the item and went home. When I got home it was a good thing that I looked at the receipt before throwing it away. Mandy wrote her name and phone number on it.

I called her the next morning. Mandy didn't have to work that night but I did. I told her that I worked from four until midnight as security at a local factory. I wanted to meet before I went to work but she had lots of errands to run. We agreed to meet at an all night diner near my job. I pulled into the parking lot and got out of my car and when she saw me she exited hers. She surprised me with a hug and kiss and we entered the diner. We were shown to a table in the corner by ourselves. I sat in the booth and she slid in next to me instead of across the table from me. Mandy looked great! She wore her hair up, a light blue blouse, a black skirt that was just above mid thigh, black stockings and heels. She asked about my day and I told her. I asked about hers and she told me about her errands then started talking about er job. She mentioned a man that would come in and purchase women's lingere for himself. She asked me what I thought about that. I think I surprised her when I said that could be sexy as hell if it was done the right way. She asked me what I meant and I told her that his hair should be styled like a woman or wear a wig, no facial hair, make up done tastefully, good taste in clothes and removal of body hair. Mandy looked around to make sure nobody could see and she took my hand and placed it in her thigh. she then pushed it up higher until my hand rested on her erect penis! She then asked me "What do you think of that"? I looked into her beautiful brown eyes, said "That is beautiful" and kissed her. I paid the check and we left. In the parking lot she asked "your place or mine"? I explained my situation and soon followed her to her place.

We got in her apartment and our clothes flew off! Up to that day I never had any sex with a man. Now here I was; kissing, stroking, sucking, licking and fucking with a full time crossdresser! I swallowed my first load of cum! She was the first person to lick and suck on my nipples. When she was clothed she looked completely female. When she was naked she looked like a flat chested woman with a penis. She even had a woman's voice. I found out later that she was nine years older than me and she started dressing shortly after high school. I asked her if she was taking hormones and she said no. Mandy explained that the guys she knew that were transitioning to female that were taking hormones either couldn't attain an erection or had difficulty getting it up. She liked her hard cock too much to give it up!

On the third occasion that we got together(at my new apartment) we had finished another round of mind blowing sex when I asked her if she wanted to fuck me. She explained that she was a bottom and that she was perfectly happy just getting fucked. She did start fingering my ass when giving me a blowjob though.

One day when we were both off work I was at Mandy's place and I was rubbing her thigh and I said that I liked that feel of her stockings. Mandy lead me into the bathroom where we took a shower. She kept her razor and shaving cream on a shelf in the shower. She shaved me from the neck down. We then dried off and she had me sit at her make-up table. She applied make-up and put a wig on me. She was maybe an inch shorter than me and our bodies were similar so her clothes fit me. My cock really got hard when I pulled the stockings on my freshly shaved legs! Mandy then proceeded to phone a friend of hers and invited that friend over for a threesome. I thought her friend was going to be another crossdresser but it was a regular man. Mandy introduced us and she started french kissing him. I got hard again watching them and she pulled "Joe" over to me. Mandy started french kissing me when I felt two hands on my ass, one was Mandy's and one was Joe's. I had never kissed a regular guy before but when I turned my head to look at Joe he dove right in. Mandy stepped back and watched us kissing and groping each other. I dropped to my knees and as I was pulling his pants down I was thinking that Mandy set this up so I could get fucked. I pulled his pants and underwear down together and was greeted with the biggest cock i had ever seen in my life! Mandy knelt down beside me and asked if I wanted that cock in my ass. I told her that I didn't want one that big to be my first. We both worked on his cock orally until Mandy had me lay down and she got on top of me in a 69 and we sucked each other while Joe fucked her!

Mandy and I slowly drifted apart. Joe moved in with her full time. They would call and invite me over for a threesome from time to time and I always went. I eventually hooked up with a man on an AOL chatroom and he fucked me for the first time!

Thanks to Sulka and Mandy I was able to get over any misgivings I had about engaging in sex with men!