Jen and Me


It started innocently enough for me, I guess. In fact, at the time, I was not really aware of what was happening. I must admit that, knowing what I know now, I would not have put a stop to it. Of course, had you told me at the start about Jen's little plan, I probably would have balked. Hell, I would have run away screaming.

Jen and I had been dating a little over a year. I had just turned 18 when we met. She was much older than I. Jen had been through an awful marriage to a violently abusive man. She was thirty when we met. The divorce was, at the time, just under two years behind her. All that was left to remind her of "him" was a crescent shaped scar, barely visible, on her back just below her shoulder. That it was caused by a broken bottle was all she would say. She has not been more forthcoming. I had not pushed the matter. I knew she would tell me when the time was right for her.

I guess, if one were to look at me and Jen together, you would wonder what the hell she is doing with me. She is statuesque at six feet. She has the lithe, tanned body of a Victoria Secret model. I am, of course, prejudiced as to anything about her, but she turns heads everywhere we go. It matters not whether she wears sweats or cashmere. It seems that everyone notices a tall, honey blonde with the long, shapely legs and an hourglass figure.

Then they see me. Mousey is an abject overstatement of my presence. If I stretch myself, I am just a little over five-three. If I dumped five pounds, I could be a jockey. My dad, I am told, though he died when I was small, had experienced a growth spurt when he was 16. That was the harshest cruelty of my youth, as I kept expecting to shoot up to at least nominal height in my teens. The spurt never arrived.

I have been told that I look fourteen. I have also been made aware, when I was fifteen, by a forty year-old perv, that I would make a stunning girl. The phrase the old guy used was "Boy, you look good enough to kiss." He said this and offered his lap to me. I would like to say that I decked him, but I never was going to be a tough guy. I just left as quickly as I could.

Ironically, I have come to believe that Jen would have never been interested in me, if I was anything but what I am. Her ex, at least what I have gathered in our time together, was one of those big, burly athletic types. Apparently, he was a professional football player, but not a big name. Again, Jen has never mentioned him by anything other than a pronoun. I have not pried. It is not my way.

With that background in mind, one might guess correctly that Jen is the dominant person in our relationship. After all, I was in my teens, and Jen was just past thirty. Many mistake me for her son, which has brought some stares when we are in public. These stares used to make us uncomfortable. Now they sometimes excite us.

It is not that I am some little slave to my Jen. We have lived together for just over three years now, and except for this one little thing, I have as much say in our relationship as I want and need.

It's that one little thing that snuck up on me. It was ungodly slow. It started when Jen took a night cosmetology class. Jen is a successful businesswoman, but she enjoys taking night classes just for the sake of learning.

One night, Jen asked me if I would help her with her school work. Even though there was an evil gleam in Jen's green eyes, or perhaps it was more because such a gleam usually ends with us in bed, I said I would help. "Help" was letting her apply makeup to my face and a feminine style to my then shoulder-length mop of hair. Even after it was explained to me, I was okay with it. I was not the most macho guy on the planet anyway. It was not as if it would cause me to doubt my masculinity any more than that perv did when he suggested I would look good on his lap.

My transformation from boyish man to what I thought was going to be boyish-man-made-up-to-be-a-boyish-man-in-women's-makeup took about two hours. I have to admit that I at least enjoyed the fact that Jen washed my hair while we in the shower together. Being five foot three has its advantages in that I am at just about boob level to Jen. As she washed and stroked my hair, I suckled and played. It probably added half an hour to the process, but it was damned well worth it.

Finally, when she had completed her artistry, Jen sat back and assessed her work. Just from the look in her eyes, I could tell she was more than a little pleased. In fact, she had this look in her lovely eyes that I adored. It was her "come hither" look. She just looked at me in silence for several moments, until I was beginning to get a tad uncomfortable.

"What?" I asked, as I sat there nude, except a pair of gray gym shorts.

Finally, blinking away her fugue, Jen replied, "Terry, you look so fucking hot."

"Yeah, right," I replied and waited for the punch line.

"No really, honey. You look, well, beautiful." Sensing my growing discomfort, Jen placed a hand gently on my shoulder, and picked up a small mirror from the table. "You have got to see this, baby."

I admit that looking at my face in that mirror was much like looking at someone else. Terry was gone and a very pretty girl had emerged. It was not like Jen had covered my face in make up at all. She had merely used just the right amount of mascara, base and blush to highlight my facial features. She had been generous with the lip gloss on my full lips, and she had given my light blonde, almost white hair a swept look that was ultimately feminine; however, all in all, she had been quite conservative. The effect was truly extraordinary.

I was kind of embarrassed about the whole thing at the time. I remember wanting to go wash my face and even shower the "do" out of my hair. As I was rising to do so, Jen took my arm.

"Wait, please," she said. "I want a picture of you." I started to protest, but just then the robe she was wearing opened a little. I decided then that this little episode might work to my distinct advantage, so I relented.

"Okay, but this pic better not end up on a webpage." I said this jokingly, but believe me, I was serious.

Laughing lightly, Jen replied, "Baby, you know I would never do anything to hurt you."

Jen had me stand with the powder blue walls of the spare bedroom at my back, while she took a handful of photos of my "new face". I might add that we were both nude as these photos were taken. With each flash, my formerly flaccid cock became more and more erect. Until, by the time the impromptu shoot was done, my cock was fully engorged and pointing stiffly and accusingly at Jen.

After setting her digital camera on the bed behind her, Jen stepped toward me. Her painted lips met my painted lips. After kissing me as passionately as she had ever done, she looked deeply into my eyes and whispered softly, almost inaudibly, "I love you, Terry."

Before I could reply, her lips returned to mine. Our tongues swirled together, as she held me tightly in my arms. Her face tilted down to mine. Mine tilted up to hers. Slowly she kissed her way down my body, as she knelt before me. Her green eyes looked longingly up into mine. Jen brushed the precum covered head of my cock with her face. The slick, transparent nectar gleamed on her cheeks.

Instinctively, my hands reached to Jen's hair and guided her lips down the shaft of my throbbing cock. Jen eagerly sucked up and down the length of my shaft. I felt her tongue slathering the underside, as she moaned around my manhood. In what seemed like seconds, I came in a shuddering orgasm with Jen's nails pushing into the flesh of my smooth ass, as she milked each drop from my cock. Pleased that I had given her the last of my seed, Jen stood and brought her lips to mine once more. As our lips met, she pushed much of my load into my mouth. I had tasted myself on her lips in the past but never to this degree. She had held much of the semen especially for our kiss. As she had taken it from me, I took it from her—willingly and gladly. In that moment, we had never been more in love. We would spend the rest of the day in bed.

Slowly, but surely, our little pastime went from once every so often to once every couple of weeks and then to a weekly thing. Eventually, Jen started laying out clothing for me. At first, it was just a thong or maybe a pair of stockings. I would always be rewarded with a good hard fucking. No red-blooded male can resist a good fucking by a beautiful woman. I knew I could not resist, even if the woman wanted me to dress like a woman, myself.

Looking back, I guess I was starting to get into it. Truth be told, I might have even been looking forward to where all this would go. As the months passed, my wardrobe increased. Soon, Jen was bringing home entire outfits for me to wear. I had gotten into the practice of shaving my legs and pits. I have no hair on my chest. In fact, even my pubic hair was no more than a wispy patch. Eventually, it was removed, as well.

By the end of a year, I was spending entire weekends dressed as "Teri"; though I had balked at leaving the house as her. It was after a couple of drinks and some very good hydro that Jen talked "Teri" into going for a late night drive. For the drive, Jen had dressed me in a little black, sleeveless dress that was terriblely short. I wore black, four-inch spiked heels to which I had grown accustomed on our "weekends in", thigh-high, black stockings and an ankle bracelet. Underneath it all, she had chosen for me a black padded bra and matching thong.

By this time, my hair was well beyond my shoulders. Jen has styled it straight for that night. It hung to the middle of my back. As we headed for the door, my heels clicking seductively with each step, Jen handed me a small clutch purse that completed my ensemble.

Jen, for her part, was a knock out, as usual, in her tight jeans and mid-rift barring black tee. She wore knee length, stiletto boots. She often went braless, and this night was no exception. Jen's firm, full breasts strained at the cotton. The bottom of her tee barely covered her round orbs. As the chilly air hit us, I saw that her nipples hardened to points. The sight caused a more than slight discomfort for me, as I was tucked tightly into my tiny thong. It was moments like these that I was forever thankful to be "nominally endowed", for I can only imagine my discomfort were I much larger.

The plan had been to just take a spin around our sprawling city. I was still much too timid to have others really look at me, so I agreed to only that. I would basically be seen only from the shoulders up and then only as we passed by other cars at the speed limit.

We drove for about half an hour when Jen said, "I want a drink. How about you, Teri?"

"I don't know about that, Jen," I stammered. I had learned, at Jen's insistence, raise and soften my voice to sound more feminine, but I guess I had forgotten in the moment.

"If we are going to make this work, Teri," Jen answered, "You might want to watch your voice. Sounding like a man might give you away. That would be bad, you know."

Her tone set me back a bit. It was no longer the loving, soft tone of the woman I had fallen in love with and adored. Instead it was matter-of-fact tone of voice that sent a shiver up my spine. Perhaps sensing my growing discomfort, Jen placed a warm, reassuring hand on my thigh.

"Babygirl, I won't let anything happen to you that you don't want. You do know that, don't you?" Her voice had returned to that which I knew best. Reassured or not, I knew that whatever was about to happen was beyond my control. I sat silently and stared out at traffic. We proceeded to a little bar downtown.

We pulled into the lot at the back of the little place. I had never been there, but I had the feeling Jen had probably frequented the place before we met. She took my hand, as we walked to the doorway. We passed a couple on the street, as we made our way the few paces to the entrance. I saw the man glance over at us. His eyes stayed on me, and I just knew he was aware that I was a man in drag. Yet, when I glanced back at him, he was smiling at me before turning back to his date. It was not a look of discovery; it was a leering look of lust. Strangely, it made me feel safer more than just creeped out.

"Ready, babygirl?" Jen asked, as she pulled the door open.

Clutching her hand tightly in my left and my purse with my right, I barely remembered to adjust my voice when I replied, "I guess so."

My legs were more than a tad unsteady upon entering the bar. Everything I recall about that moment feels so surreal; it was like stepping into another world. Only it was not the world which had changed. It was I who had been altered.

I had hoped to go unnoticed, but that was not in the offing. My suspicions about Jen having been there in the past were confirmed immediately. Even the girl taking the cover charge and the bouncer checking IDs greeted her warmly. The cover charge girl even stepped from around her small counter and hugged Jen. I was introduced to both as Jen's "girl", Teri. Neither of them seemed to pay me much attention. Both had their jobs to do, and the place was staring to fill up. I took that as a good sign. I relaxed but only a bit.

Except for the dance floor and bar areas, the place was quite dark. I was grateful for that and assumed that Jen had chosen this place for that reason. Though, she might have chosen it because it had been one of her haunts, before she and I met. Whatever the reason, we made it to a booth along a wall not far from the dance floor. I was relieved that Jen had not chosen a table closer, because I really did not need to be sitting in anything but near-pitch darkness. The only light, at our table, was a small, dim lamp above us on the wall.

Even then, I was scared to death. I had done this, at least in the beginning, just to please Jen. Yes, I had come to enjoy the feel of "dressing pretty", as I had come to think of it, but I did not want to get my ass kicked for it. My mind kept churning over the possibilities. The most likely scenario I imagined was a gruff, decidedly male voice shouting "queer" at me, just as a boot strikes my already bloody and bruised face.

Jen bought us a couple of cocktails from the bar. My eyes did not leave her. I was going to run to her, if needed. I only hoped that she would have her bouncer friend keep my imagined future attackers at bay, as we ran to Jen's car in the lot. As she made her way to the bar and then back, she laughed and spoke with several people. She was obviously a former regular. I sighed softly. I began to believe that I might survive the night.

When she returned with the drinks, mine a Vodka Collins, hers a Crown and soda, I began to survey the crowd. The dance floor was starting to fill up, I saw. One thing caught my eye. Not only were there a good many male-female couples dancing, but there were also several same sex couples on the dance floor.

Jen had slid over beside me in the circular booth. Her soft hand was stroking up and down my stocking-clad left thigh. I leaned to her and whispered, "This is a gay bar, isn't it?" Squeezing my thigh gently and softly brushing my lips with hers before speaking, Jen answered, "Not 'gay' exactly, but pretty much anything goes here, baby." She let her hand locate the soft flesh just beneath the hem of my skirt and just above the top of my stocking and added, "Babygirl, I told you I would take good care of you. I love you far too much to ever hurt you."

I was emboldened by what she had said. I pressed my lips to hers and kissed her passionately. She returned my kiss with an ardor equal to mine. I began to finally relax. I no longer feared for my safety.

Indeed, as I studied the crowd in more detail, I saw that there were others like me. In fact, they were, at least in my opinion, much more obviously men in drag than I. There were a few who looked fairly ridiculous in women's clothing. One "girl" was just over six-five. Unlike me, "her" facial features did not tend toward the feminine to any degree. If "she" could pull it off, and it looked like "she" was having no problems, I figured I was quite safe. Not only had I not over done it (by now, I was applying much of my own makeup); my frame and face were very feminine. I even took out my compact and reapplied my lip gloss, having lost much of it kissing my girlfriend.

We had a few drinks. I'd had a few more than Jen. She was driving, so she was taking it easy on the alcohol. After a couple, she had foregone the Crown and sipped soda most of the night. I was feeling no pain when Jen asked me to dance. Even three-sheets-to-the-wind as I was, I hesitated, until she smiled and said, "It's okay. Everyone thinks you are my girlfriend. They'll be nice, baby."

Rubbing my crotch as she spoke did not hurt her argument, either. Soon we were on the floor dancing to a hip-hop tune. I had always been drawn more towards classic rock, but somehow "Teri" seemed to get into R&B and more dance-oriented music. It took me a little bit to get my bearings on the heels. While Jen had me dance for her a few times at home, I had mostly stood in one place and had shaken my ass for her. Dancing on a slick dance floor in spiked heels was a new thing for me.

When the first song ended, a slower song came on. I was about to leave the floor, but Jen pulled me close to her. As I leaned my head on her ample chest, she held me close with her hands sliding down to my ass. At first, her hands were on top of my skirt. Then, leaning down and kissing me in a long soul kiss, Jen lifted the back of my skirt and placed her hands onto the bare cheeks of my smooth, round ass. My cock hardened. Even though it hurt, since it was tucked in and odd position, the pain somehow made it more erotic.

Somewhere in the midst of the kiss and our slow, swaying dance, we were joined by a man with whom I had seen Jen talking earlier. Jen's hands slid to my hips, and I could feel him position himself at my back. With Jen pulling me forward a bit, I felt his crotch rubbing at my ass. I tensed a bit, both because it startled me and because it also felt very nice. "It's okay, baby. Jim's a friend. He's cool," Jen whispered softly in my ear.

I relaxed, and in spite of the fact that I had never been touched by another man before, I pressed back into him. He was so hard that I could feel the ridge his cock made in his trousers, as he pressed hard to me. He was literally humping me amid the throng of people dancing on the floor. When the song was over, Jim joined us at our table.

"I suppose I should introduce you two properly," Jen laughed. I had slid in and crossed my legs under the table. "Teri, this is Jim. We have known each other for ages." Turning to Jim, she added, "Jim, this is my girl, Teri."

Jim smiled brightly and took my hand in his. His hand was enormous and very nearly swallowed mine. "It's very nice meeting you, Teri," he said, his smile never fading. I nodded politely. I was at a loss for words, at the moment.

Jen leaned towards me and whispered that Jim was into girls like me. In proof of that, Jim, who had not yet released my hand, placed it on his bulging crotch. It was so big in my hand.

Instinctively, I gripped it and began to massage it. Jen was kissing my neck, by this time. Jim released my hand and reached down to stroke my inner thigh, his own lips pressed to the other side of my neck. I began breathing heavily. I had never felt so desired in my life.

Sometime during all the petting, Jim had somehow unzipped and released his long, thick member from his pants. My thumb brushed over the tip, smearing a generous amount of precum over the head. It was almost like an out of body experience. I was stroking the cock of another male. I was enjoying him kissing me. It was then that I heard Jen say, "Go ahead, babygirl. I know you want to. Suck him."

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bybarry_nine© 15 comments/ 117201 views/ 34 favorites

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