Falling for Tammy By Sniffme Cioc Copyright 2008. For posting to Nifty Archive. All other rights reserved.
I was the world's biggest nerd in high school. At 16 I was a virgin, desperate for physical contact, but completely unable to do anything about it. Every conversation with a girl ended with her either yawning uncontrollably or backing away nervously. I think that impossible gulf between me and all things feminine contributed to the almost constant hardon I carried around between my legs. I was always reaching into my pocket to adjust my prick and I know the girls often saw me doing it because I would hear them giggle and see them whispering to each other.
Looking back, while I wasn't Brad Pitt, I wasn't a bad looking guy. I was 6 feet tall, very thin, pale, dark brown hair, pink nipples and a circumcised 6 inch penis. I had a few friends who were at least as nerdy as me. We used to work on experiments together while quoting entire scenes, word for word from Star Trek. It is not hard now to understand why the girls stayed away in droves.
My one other friend was named Tommy and lived in my neighborhood. He was two years younger than me but just as strange. While we didn't have much in common, he lived close and his parents never seemed to be home so we hung out pretty often. He had an interesting face; almost pretty with full red lips and sandy blonde hair that was always long and shaggy. There was something vaguely feminine about him that put most people off, but it didn't really bother me.
At some point I guess he discovered masturbation because he started asking questions about how I did it and what I fantasized about. All this made me pretty uncomfortable and I would usually just change the subject to something safer. At the same time I noticed that he had started dressing a little differently. It was hard to put my finger on at first, but colors were suddenly more vivid, fabrics a little softer, shorts a little tighter and shorter and tops cut a bit lower. He also seemed to be wearing a little makeup and sometimes I was sure I got a whiff of perfume.
I didn't think much about his gradual shift until the day of his 15th birthday. As I was his only friend, he didn't bother to have a party, but invited me over, saying that he had a big surprise for me. I knocked on his door and when he answered I was shocked to see him dressed completely as a girl. What I saw was a beautiful girl who looked familiar, but not quite. I stammered asking if Tommy was home, then realized it was him.
"Dude, what the hell are you doing?" I said as he dragged me into the house and shut the door. He leaned back on the door with his arms behind him seductively and asked, "I'm Tammy. So what do you think?" It took a moment to absorb it all. The transformation was complete and amazing. He was a knockout, at least as pretty as all those girls I masturbated over constantly. He was wearing little white sandals that showed off his pretty feet with red toenails. His legs were shaved and perfectly shaped. He was wearing a tight short pink skirt and a low cut yellow sleeveless top that showed off his little breasts. The look was completed by a gold necklace and little dangly earrings. His lips shined with gloss and his eye makeup really brought out his sparkling blue eyes. It was just too confusing. My penis immediately hardened looking at her, then softened as I remembered that this was my slightly weird friend, Tommy.
"Tommy, this is just too weird for me. I gotta go," I said walking to the door. He placed his hand on my arm and rubbing his other hand across his chest he seductively asked, "come on, don't you think I am pretty?" I jerked my hand away and shouted, "Dude, are you serious? You are a fucking guy! This is the weirdest thing I have ever seen in my life. What are you, some kind of a fucking fag!?" The effect was immediate and terrible. He was crushed. I guess he thought I would love the look and he immediately broke down and cried, but it didn't stop there. He slumped down onto the floor, leaning against the door, with his head in his hands, sobbing so hard that his whole body was shaking and I wondered if he could breathe.
Between sobs he apologized over and over telling me that he did not know what had gotten into him. That he was so sorry he had offended me. That he would never do it again. I felt terrible and knelt in front of him asking him to stop crying. Telling him it was ok. That I didn't mean to be so harsh. He looked up at me with tears and mascara running down his pink cheeks and said, "I am so sorry. I will never do this again." I reached up with my thumbs and wiped the tears away and said, "let's talk a little."
I asked what was going on and he said that he loved dressing and acting as a girl. I asked how long he had been doing it and he said since he was 9. He told me that he had been wearing girl's underwear and nightgowns exclusively for a year and that when he was alone he usually dressed completely as a girl. He showed me his closet with all sorts of girl clothes and opened a secret drawer and showed me all his underwear. It was filled with beautiful lacy, silky things and I couldn't resist reaching my hand out to touch them. He reached for a pair if red satin panties and handed them to me saying, "feel them. They feel wonderful don't they?" As I touched them I had to admit that they did and added that they felt really sexy. He smiled knowingly.
He told me that in all those conversations about masturbation, when he was talking about girls, he was actually thinking about guys. "really?" I asked. Wow, that is strange. "have you ever had sex with a guy?" I asked.
"No, no. Not yet at least," he replied.
"But you want to?" I asked.
He looked down and fiddled with the panties in his hand and looked back up into my eyes and said, "maybe. I think I do...but only with the right boy."
At that moment he looked so vulnerable and pretty I actually wanted to kiss him, but I didn't and the moment passed. We talked a bit more and eventually I went home with my head spinning.
For the next few times we were together Tommy was back to normal, but the femininity was definitely there and growing. He didn't wear dresses or overtly girly clothing, but there was always just a bit of eye makeup, his hair was always nice and he almost always had on those tight short shorts. He was usually just my pal Tommy, but occasionally, when he sat just right I would catch my eyes following those lovely legs all the way up to where they disappeared into those red silk panties and I would have to look away to get myself back together. When we were apart, I thought of sex all the time as usual, but occasionally my mind would wander to Tommy. An image would pass through my mind of his thighs or his butt or his mouth or cheek. At first I fought it, but more and more I just went with it. It was feeling less and less gay as I found myself thinking of Tommy more and more as Tammy.
One Saturday morning I dropped by and he had the house to himself as usual. He asked if I wanted a glass of wine. This was new. I had never tasted alcohol and while I was a bit nervous about it, I decided to give it a taste. He went to the refrigerator to get the bottle. As he did I noticed for the first time what a sexy butt he had. It was round and protruded sexily. The short pants showed his crack off so deliciously that I had to reach down and make a quick adjustment in my pants. As he turned around I know he saw me adjusting, but said nothing as he poured the glasses.
The wine was nice. Better than I expected and we finished a glass quickly as we talked. Tommy refilled the glasses and suggested that we go to his room. When we got there he said he had a surprise for me, then seeing the sudden look of horror on my face shouted "don't worry! It isn't like the last surprise!" We both burst out laughing so hard that we fell against each other spilling wine all over the place. My head was spinning and warm. He brushed the wine off my chest and I remember thinking how nice it felt having his hand on me.
I said, "ok, let's see this surprise." He took me by the hand into his parent's room and opened the closet. He took down a box from the top shelf and turned to look at me with a smile. "treasure," he said with an impish smile and led the way to his room. He opened the box and inside was a stack of porn magazines. I had seen porn a few times on the internet, but my parents kept the computer pretty locked so this was indeed a treasure trove. We sat on the bed cross legged with the box between us and each took out a magazine.
The first one I saw was about girls with huge sloppy boobs. It was cool, but the girls looked harsh and old and I put it down pretty quickly reaching for another one. The second one was a gay magazine showing guys sucking each other off and having anal sex. I looked at it a moment and laughed, handing it to Tommy saying, "here bro. this one has YOU written all over it." He looked for a moment and said, "not quite," which actually surprised me.
Tommy looked into my eyes shyly and pointed to the next one on the stack and said, "try that one. It is more my speed." On the cover were sexy young girls but when I opened it I was shocked to see that these pretty young girls all had penises. Oh my god. I was immediately hard as a rock and couldn't do a think about it. "wow," I said. "Is this real? This is amazing. " The girls were truly pretty. They were young with warm soft skin, perky small breasts, absolutely luscious asses, and, well, cute little penises. And they were very very sexy.
I was captivated as I scanned the picture, drinking in every detail. The girl's nipples were little rounded cones on top of little cone shaped mounds. Her stomach was flat and sexy with a gold ring in her navel. She had a patch of dark pubic hair and there, between her sexy thighs hung her small penis that could only be described as intensely sexy. Her little cock was surrounded by a slight mound of what looked like creamy soft skin and I found myself imagining what it would be like to kiss him/her right there.
I looked up to meet Tommy's seductive eyes. "pretty sexy aren't they?" he said. I wasn't sure what to say, but gulped and said, "Yea. I never thought I would say this, but I guess they are." We sat there staring at one another.
After a long silence Tommy finally whispered, "do you ever think about Tammy?"
"sometimes," I croaked.
"she thinks about you all the time." She said My hands were shaking, my mind was reeling and my cock was rock hard as she whispered, "would you like to see her, now?"
I blinked, trying to think of a way to say no, but my mouth got there first saying, "yes. I would like to see her very much."
He leaned forward ever so slowly and brushed his lips against mine. In that moment everything changed. Tommy was now Tammy in my mind and I wanted to be as close to her as possible. I kissed her back awkwardly as we gazed into each other's eyes. Her perfume was intoxicating.. I couldn't take my eyes off of her. As we kissed again I felt her tongue pressing against my lips and I opened my mouth to allow her in. Her tongue felt warm and exciting and alive. I could taste her saliva, smell her breath and feel the warmth of her face against mine. As we kissed the thought came into my head that I was about to make love for the first time in my life.
She whispered in my ear, "Stay here. I will be right. She jumped up and ran to the bathroom and I caught a glimpse of her pretty ass as she looked back blowing a kiss just before closing the door. I was suddenly alone sitting on my friend's bed surrounded by porn, terribly confused. I wasn't sure how this worked. What was I supposed to do?
In just a moment the door opened and out came Tammy in all her glory. She was wearing a blue teddy that matched her eyes. It was very short, coming down even with the bottom of her blue silk panties. Her bra matched the panties. She was barefoot and I was struck by how feminine she looked as she walked toward me slowly like we were both dreaming. She stopped and turned slowly then looked into my eyes for a moment. "You are so beautiful." I exclaimed and her eyes filled with tears.
"I am going to make you so happy." She responded. She swept the magazines onto the floor and climbed onto the bed on her knees. She took my cheeks in her hands and kissed me long and deep, exploring my mouth with her tongue. I was in heaven. This was truly the woman of my dreams and here she was, in the flesh, wanting me as much as I wanted her. It was almost too much to comprehend.
As I sat there dumbly she took the lead and pulled my t-shirt up over my head and cast it aside. She pushed me back on the bed and removed my shoes, socks and pants, leaving my underwear. She leaned down again with her face near my crotch and looked up at me saying, "I have never done this, so be patient." I watched her as she touched me through my underwear, outlining my hard penis with her finger. She placed her fingers around it as though she was gauging its size. She looked at me and reached for the elastic of my wasteband and slowly pulled them down, lifting them to clear my throbbing member.
She looked up at me, her face only a couple of inches from my penis and said, "it is even more beautiful than I imagined." Then caressed it so softly and lovingly for a moment then she kissed it softly. It jumped in response which made her smile. She opened her mouth and licked it with the tip of her tongue saying, "mmm. tasty." I noted that her tongue was exactly the same color as the head of my penis and reveled in the delicious feeling of her slippery tongue against my sensitive skin.
My penis rose higher and she reached out with her hand and lifted it into her mouth. With our eyes locked together she kissed the precum covered tip and let it slip between her full red lips, for a moment. "mmm" she muttered as she swished her tongue around the head. I felt so tightly connected to her as we both explored amazing sensations for the first time. "oh god Tammy." I whispered, unable to even speak. I saw the corners of her mouth smile a bit then she started sliding down my penis ever so slowly. Truly, that was and remains the single most exciting thing I have ever experienced in my life.
I felt dizzy like I would faint. I could feel the warmth of her body draped across my thighs and could see my very wet cock sliding in and out of her mouth. I reached out and stroked her cheeks as I moaned loudly and thrust my hips to go deeper into her mouth which was locked around my penis. It was such a wonderful site. We continued that way for maybe a minute before I realized that I was about to explode. I tried to pull out of her mouth, saying, "I am coming!" but she held on and just replied, "mmmmmm." Hearing that I let go and blasted what felt like ten shots of cum into her mouth and she swallowed it all, continuing to slowly slide up and down. As I softened she slid her mouth off me and squeezed my penis between her thumb and fingers, milking out the last drop out onto the tip which she rubbed onto her soft lips like lipstick which made us both giggle.
She slid up my body and lay on top of me, her legs spread, her thighs gripping me, our crotches touching. I felt the small mounds of her breasts and a hard bulge in her panties against my soft cock. She kissed me softly with her slippery wet lips and I smelled my sperm on her breath. It was intoxicating. I grabbed her and kissed her as hard as I could, licking all around inside her mouth. With my right hand I reached down and felt her perfect soft, satin covered ass. It felt so good and I felt my cock start to rise again. I squeezed her butt cheeks and slipped both hands under the fabric of her panties to feel the warm flesh. We moaned into each other's mouths as I explored, running my fingers up and down the crack. As I touched her little hole she moaned loudly so I did it again and felt her rise to meet my fingers. I pressed a bit and my finger slipped inside. I realize now that she had lubed herself, but at the time I was just amazed at how hot she felt inside.
"I want you inside me, my love." She whispered slowly pushing her butt against my probing fingers. I was confused, "in here?" I asked. She smiled and nodded yes and before I could think about it too much she raised up enough to remove her panties then straddled me on her knees. My cock was fully hard again and she slid it back and forth along her butt crack which felt amazing. It was so slippery and it felt like it belonged there. Each time it could cross her tight little hole it would slip inside just a bit, deeper and deeper with each pass until she stopped and slowly sank down on my hard cock. She gasped as it entered her and I think it hit us both simultaneously that we had just become one in some crazy spiritual way. She placed her hands on my chest and I caressed her forearms as she rose up and down on me.
It was wonderful. After a moment she pulled the teddy up and off, tossing it aside and I saw this beautiful girl, wearing only a blue silk bra, looking lovingly into my eyes, fucking me like crazy. I could feel her butt cheeks against the sides of my penis as she rose up and the softness of those globes against my thighs as she came down each time. After a few strokes I became aware for the first time that her penis was rubbing against my stomach each time she lowered herself.. I looked at it and was amazed at its beauty. Unlike mine, hers was uncut, with a soft covering over it coming to a point with soft wrinkly skin at the tip. The tip was dribbling precum. I reached out for it and it felt strange. Like mine, but different. I slid my hand all over it enjoying the warmth. I cupped her balls in my other hand and caressed the soft skin. As I jacked her penis up and down it started to rise, feeling alive and exciting, its head peeking out of its little foreskin hiding place. I continued to jack it as she continued to rise and fall on my cock. As her pace intensified I matched it with my hand and could feel the intensity building in both or us until she screamed and started shooting hot semen onto my hand and stomach. I think it was the wonderfully sexy smell of her cum that pushed me over the edge and I came into her butt with almost as much intensity as the first cum.
She slowed her pace then stopped and leaned down to kiss my mouth. I let go of her penis and put my arms around her, pulling her close to me. Our hearts were pounding together. I slid my hand down and played with her slippery asshole that was oozing my cum. As I did she slid her body along mine slowly, lubricated by her cum that was between us. As we fell asleep that way I realized we were both changed forever.
I spent more and more time with her making love for hours, exploring every possible position and style and falling deeply in love with her...
Copyright 2008 sniffmecioc@yahoo.com
Posted on Nifty by permission. All rights reserved.
Comments welcome.
xoxo -sniffme