From our 1999 archives:
Teaching him to like it by Hulka
My first boyfriend was predisposed to cross-dressing. Evidently, he played dress-up with his sister and cousins when he was young, according to his Mom, so I don't feel so guilty about what I did to him later on, because it was obvious that he was happier being a girl. We had an emotional connection and he was there for me when I needed someone who cared. I loved him very much.
This is our story.
I had met Scottie in the most innocuous of ways...at the shopping mall. I was browsing in a record store, and saw him staring at me. I smiled at him and he smiled back. I asked him what kind of music he was buying and he nervously showed me a Pet Shop Boys Album. I said I had never heard of them, but they looked interesting. I asked him a little about Minneapolis, and he and I talked about the terrible winters, and the parks and lakes. I made a move to leave and he said wait he would go with me. He purchased his tape, and he followed me out into the mall. We walked around the mall, and he just sort of hung with me. I was hungry and said I wanted to go get a hamburger, and would he like to go with. He said YES, and we had lunch, followed by me taking him home.
The next day he wandered by my house, and invited himself in. We ended up spending several weeks with him coming over on weekends, helping me with chores and running errands.
I was new to the Twin Cities, recently divorced and appreciated the company. He was very appreciative of the fact that I listened to what he had to say, and that I was very happy to take him with me to run errands, grab something to eat and so.
After a while his appearances were very routine, and he was staying over to eat dinner and watch television. His parents didn't seem to mind and didn't seem too interested in him. I learned that he was not a very good student, and I began helping him with some compositions for English, and going over his math homework before he handed it in.
It occured to me it was inappropriate for a young man of 18 to be spending so much time with a middle aged divorced man aged 35. But he was very enthusiastic and appreciative about the time we spent together. And I was lonely and knew no-one in the Twin Cities. And he was pleasant to be around.
Of course it was more than just companionship and at the time I didn't understand it..but I enjoyed looking at him. He was very good looking. He had the most amazing dark blue eyes. His hair was dark honey blonde, but he did a lot with it..including highlights and wearing it semi-long all brushed out and wild looking. He was relatively small for a young man of 18...about 5'6", and was slender and healthy looking.
He was also very well groomed and vain about his appearance. It was very unusual for a 18 year old guy in high school to be so facetious about his appearance. I found it amusing, and mysteriously attractive. He had an effeminate quality, but very subtle and not in any way disturbing or offensive...what they sometimes refer to as 'nellie'. Because of this I was never uncomfortable taking him with me to the neighborhood hardware store, or walking in the neighborhood, or taking him to a local resturant.
He was always dressed very fashionably and expensively for a teenaged boy too. He loved GUEST jeans and high fashion shirts. I was endless fascinated with his shoes which were always the slip-ons with little tassels...he called them "Pimp Shoes." He had several pairs including one pair that was gray but I always was taken with his habit of wearing white socks with his "pimp" shoes. And they were not athletic tube socks either, but very nice white cotton stockings.
But most of all he was young, he was energetic, was always smiling and laughing. Most importantly, he wanted to spend time with me. I was lonely and I appreciated his company. I knew that I had a sexual attraction but it was 'unspoken' secret that I tried to deny.
One evening he was sitting on the bed in his stocking feet, helping me fold laundry in my bedroom. He was yaking aimlessly about a bunch of nonsense concerning school, his overweight girlfriend's diet trauma, his sister and so on. His leg was touching mine and he was staring directly at me with those deep blue eyes. Suddenly he leaned over and kissed me on the lips, looking directly into my eyes as he did it. I immediately pushed him on the bed, and began kissing him deeply. He kissed back enthusiastically. He put his hand on my legs and the other on my crotch and rubbed. I began to unbutton his shirt and undo his belt. He did the same to me. We were kissing deeply all the while.
I unzipped his jeans, and was shocked to see him wearing a pair of red satin thongs underneath his jeans. I looked at him and he smiled back. So I continued to undress him.
Before long I had him naked. I turned him over and stared at his butt. It was round and muscular and actually very large for a guy. I went on top of him and rubbed my dic-k between his legs. He made little crying sounds that made me want to continue. I wet my dic-k with some spit and he took it in his hand and guided it into his ass. It obviously hurt him as he cried out in pain, but I didn't know what I was doing and just pushed it in. After a while Scottie began making little "whews" and "awes" that definitely were not expressions of pain anymore. I was freaked, cause this was plainly wrong for an older guy to be sticking his dic-k into an 18 year old kid. But Scottie didn't think so. He turned his head to look up at me, and he was smiling. So I just continued to fuc-k him. It felt so great, and I hadn't fuc-ked a girl for over a year.
After that our relationship became increasingly sexual, and we experimented with different lubrications and ways of fuc-king. I never knew how wonderful it felt to fuc-k a guy.
He was so open and free about the sex too...no guilt trips like with girls. And fuc-king a guy was also a big ego thrill for me that such a handsome guy could be made to be so soft and submissive by what I was doing to him. I become fascinated with the idea of shaping Scottie's sexuality into being totally like a girl. I studied up on male anatomy and gay sex. I learned that about the prostate and how important it was in gay sex. I learned a lot about making the experience a pleasure for both of us. It was great.
As our sexual relationship grew my guilt about being gay was beginning to be a problem. But it was partially overcome by the fact that Scottie began to look more and more female to me in his physique and his mannerisms. Especially while we were alone. It was like we shared a special intimacy that was hidden from the rest of the world. This was an endless fascination to me for some reason. I thought he was amazing because he was always eager for a sex unlike the girls I had known, and he was completely uninhibited and participated enthusiastically without any judgment when I made mistakes (and I made a lot of them). I was particularly aware of how he began to walk and became intimately aware of his legs and his butt which were shapely, but no mushy soft like most women. He seemed to become an amazing hybrid of boy and girl...the best of both worlds I told myself.
When I suggested he wear a dress, he enthusiastically came over to my house with about 6 dresses his sister wore. He was only an inch or two taller than his sister, and her dresses seemed to fit him fine. So we spent the afternoon celebrating his body and how it looked in women's clothes.
Later on we began to get him his own clothing. As a reward when he was thoughtful or was especially helpful in doing housework or cooking dinner for me, or something positive occurred in either of our lives---like a raise or good grade at school---I brought home an outfit for him to wear. He got his own high heels---he had a pair of white pumps and a pair of black pumps. But I picked out many of his outfits. We also started going to gay bars and special events with him dressed up. It was easy for he and I to fit in at a gay bar. The Twin Cities has a large gay community, and lots of gay fundraisers and special events. Scottie went to all of them dressed up with me as a his lover.
We did it all---garter belts, hose, bras or corsets or Basques or Nighties. He would dress up and apply his make-up. I would watch and prepare champagne. And we would make love for hours in front of a mirror I rigged up. We made major use of mirrors. We would watch how his body looked in the lace and satin. He would arch his back and throw up his hands out and his head up. He was very good at arching his back and offering me his ass. And we would watch as my body connected to his. I was very oral in rewarding him for being passive and effeminate. The more effeminate and passive he would be--the more oral sex he would get from me.
We also fuc-ked like bunnies. We loved to fuc-k. But I would never allow him to c-um unless I was inside of him. That was the rule. He only could c-um with my dic-k inside of him while I jacked him off. It was my goal to change his sexuality so that he required a dic-k inside him to c-um. It seemed to work, cause after the first year, he was asking me to fuc-k him so he could c-um. He would beg me to fuc-k him so that he could c-um. During the entire three years together, it was very rare for him to c-um without my dic-k inside him.
Our lovemaking would last for hours. I would orally service him watching my mouth along the curves of his body. I would prepare him for fuc-king with my lips and tongue. Most of the time, I made him turn over on his stomach while I fuc-ked him and had my way. He was only allowed to c-um after I was done. I thrust hard and deep as I could so as to get a big load off and make him warm and wet inside. After I would c-um, I would turn him over with his feet in the air and on my shoulders, with his knees against his chest. In his stockings and high heels and his feet in the air with his faced flushed and his pen-is in full erection---he was so sexual.
In the back of my mind was the fantasy of making Scottie into a total girl as far as his sexual preferences were concerned. So I paid strict attention to making sure that he was serviced like a girl. I would try so hard to time my thrusts inside him with the strokes up and down on his coc-k to maximize his orgasm. I made him hold out for a long time. I knew that anything I could do to delay the ejacuation was pleasurable and I wanted Scottie to relish and experience the time he was being fuc-ked for as long as possible. When he started to c-um, I would slow down for a minute and then begin again so that he wouldn't c-um right away. When he finally came it spurted up in the air. The higher the spurt--the better I liked it. Sometimes he would spurt a foot in the air. That would make feel very proud that I had made him mine to c-um so hard. The other rule was that he had to kiss me just after he came. He automatically would pucker up and reach up to me for a kiss after he came. If he didn't I would get mad.
Another thrill was to watch my c-um drip out of his ass and down his leg as he got up from the bed. We felt we belonged to each other because our feelings were so intimate. I was so in love and in lust also. He was the only one for me. I was totally happy.
One particular time he found a box in my basement with the hat and lace veil my ex-wife had worn at our wedding. He put on a white lacy Basque and white lace hose and then put on the veil and surprised me. He, off course, had red lipstick and great makeup on. He did not wear wigs, but had beautiful hair that he curled and fixed up. He didn't have long hair, but somehow he made it effeminate. He wore pearls around his neck. It was such a sexy exciting thing to do and what a way to get back at my ex-wife--the bitch.
As I got to know his family it became apparent to me that crossdressing was not new with Scottie. He was obviously comfortable with it, and he seemed to apply his makeup and make up his hair so effortlessly, that it was like he had been doing it for years. I later learned from his mother that Scottie had been playing with dolls and dressing up with his sister and girl cousins when he was younger. She had not punished him for it, and just chalked it up to a "phase" he was going through. Also, I learned that her bother, Scottie's Uncle, was gay, and at one time was pretty flamboyant. But I had to admire his family that they loved Scottie enough to accept him as he was.
When I look back at those years, I am not sure who was dominant or in control.
While I was ostensibly the one who played the guy and he was passive-submissive and effeminate, I became so addicted to him, to his body and to his sexuality---that he was probably the one who controlled me. When we broke up, it was extremely difficult for me. I almost committed suicide. His breaking up with me was my coming out experience. I had never considered myself "gay" because Scottie was so effeminate and our relationship seemed to natural to me. I was forced to c-um to grips with who I was and what I wanted. I have never been the same.
The story became very sad, though. In the end the age difference was a bigger obstacle than we had realized. One of worst or our disagreements centered around the fact that Scottie did not seem to be interested in College or any career other than the job as "host" at the Denny's restaurant where he worked for many years. I was adamant that he get a job with Northwest Airlines to be a flight attendant.
I knew that the best thing for both of us was to be independent financially, travel and so on. But Scottie thought I was rejecting him. His mom wanted him to move out of the house, and I didn't want him moving in with me unless he applied himself in getting the job at Northwest Airlines.
He ended up leaving me. The guy he ended up with liked the "All-American Boy" look. The new boyfriend was a bartender at the local gay bar. He hated the cross-dressing and while he was a pretty good lover, I am sure that cross-dressing was never again part of Scottie's sex life. But he was very generous and got Scott a job at a gay bar. He bought a house for them and provided Scottie with the security that he wanted. Scottie was allowed to dress up a couple of times a year, but his new lover never accompanied him or supported him.
It was so sad to watch Scottie going out by himself to drag bars or parties. But by that time I was into another relationship with an older and more mature guy. And Scottie is still with this guy and is a coc-ktail waiter at a gay bar in the Midwest. This is 8 years ago. Scottie is beginning to get fat and get some lines on his face. I know he is not happy. His lover is older and is beginning to get sick. I feel sad to watch and think about what he has missed. I loved him so much.
A love like Scottie comes only once in a lifetime. Don't you think?
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Betty Pearl's Sissy Stories 20.1
Topic: Teaching him to like it by Hulka (Read 16907 times)
