How Nathan became Natalie Ch. 01

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wife turned me into a feminine crossdressing cuckold husband and her "sister" and then later helped me transform into a woman.

My wife Jennifer and I grew up together and had been around each other since we were born only two months apart. Our parents were best friends and Jennifer's parents were my Godfather and Godmother and my parents were her Godparents. We grew up in a small town that was very tight nit and almost cultish in a way and was very suspicious to outsiders. We were both homeschooled by Jennifer's mother who was a former teacher and she was my best friend and I was hers. We never argued at all; not once did we fight or raise our voices in anger to one another as we grew up and it was just common knowledge in our small town that she and I would marry and no one thought otherwise including us.

As we grew older, went through puberty and adolescence or bodies naturally changed and developed. Jennifer grew into a very lovely young woman. She had natural dirty blonde hair that came down to the middle of her back, natural light tan skin tone, a well-shaped body with perfect 32c cup breasts, a very well-shaped butt, and nice long legs. Jennifer was also very athletic and loved sports and competition and had natural leadership ability. Even though we were homeschooled due to state law Jennifer was able to play softball and soccer for the counties public school system and due to her friendly nature and leadership qualities and competitive nature she was named captain of both teams her senior year. She often bossed me around and we normally ended up doing things she enjoyed more than things I did growing up, but I never complained. She was not a bitch about it nor would she get mad or angry if I declined but she would more "lead" me into the direction of what she wanted to do.

Me, I developed differently. I was always a pretty boy type. Not to brag but I was. Not handsome in a masculine way but pretty in a feminine way. I grew up or lack of growing up to stand only five nine, Jennifer was five seven; thin body that by the time I was eighteen and going to college I only weighed one hundred and thirty pounds and Jennifer weighed one hundred and fifteen pounds. My body would be described as feminine looking also including my butt, which was small but shaped like a girl's. I have black hair that by eighteen came down just past my ears on the side and just below the collar in the back and was fuller on the top. I was not into sports at all and actually sucked at them but did enjoy watching sports and seeing Jennifer play so I went to all her games, even the away ones with her parents or alone when I was able to drive. Due to my looks and body type kids my own age I met not from the small town where I grew up called me a twink, a sissy, a femboy, and even more cruelly a "faggot". But I was not or at that time did not think I was. By age eighteen Jennifer and I had kissed, which she initiated, and had more heavy make out sessions and she gave me a blow job when were both seventeen and I got aroused from it all. We had not had sex but I knew that was just a matter of time for us when she was ready because I wanted to.

After we graduated we both went to college, the same college. It was a smaller but well recognized university for academics in the same state where we grew up. The college had sports teams that played in a very low division and conference and did not have scholarship athletes. Jennifer made both the softball and soccer teams. At college Jennifer was the more popular one and started to develop friendships with the other students, both male and female, while I remained much more reserved and still very shy and once again I was "classified" as a twink or sissy gay male but at college it was different in the fact I was not called such by most people to "bully" me. Instead it was more that some of my fellow students seemed to well...appreciate that they thought I was a twink gay male? I don't know how to phrase the way they looked at me but I had more friends who were girls than male friends because the girls liked to confide in me and think of me as their stereotypical gay male friend and the girls I was friends with would often tease in a friendly manner that I was prettier than they were. I was even asked out on dates by some of the gay male students and even hit on from one of my male professors. Most people did not believe me when I told them I was not gay and some even tried to tell me it was ok to "come out of the closet" in today's society. Then when I told them I was Jennifer's boyfriend that got a huge laugh. No one believed that a girl as pretty would date a feminine looking and acting boy such as me; that was until Jennifer confirmed the fact that yes I was her boyfriend.

Jennifer had developed into a truly lovely young lady. She grew her dirty blonde hair out to where it came to the middle of her back and it was naturally wavy, her face had that innocent girl next door look but her green eyes and perfect smile gave off a hint of mischievousness and she could look at you in a way when she gave her flirtatious smile that read "I am not as innocent as I look", her body was about as perfectly formed as a girl could get with well-formed 34c sized breasts that had no sag in them, a thin waist, and what the boys and even some of the girls on campus called a "perfect" ass. My best friend and girlfriend had not only the looks but she also had sex appeal and could appear sexy just talking to someone. Jennifer had a lot of friends on campus, both male and female, socialized much more than I did, would often have to "force" me to go to parties with her since I spent most nights studying, and if I would not go she went with her friends or by herself. I was never jealous of the attention she got from the male students, some female ones, or even a few of the professors; I just counted myself lucky to be dating the prettiest girl on campus and I trusted her completely. After all we had grown up together, were best friends, and made a pact when we were younger we would never lie to each other or have secrets between us. I knew if she ever felt she wanted to date someone else she would tell me. That was our life at college and it was not until our junior year that I learned our pact of not having secrets between us or lying to one another was not as easy as I thought, and the secret and lie was mine and not hers and was also when I discovered that everyone was right about me...I may be gay or at least bi sexual.

Kevin was a senior when I was a junior and he played a defensive safety on our college's football team. Our college had only recently started a football program five years ago and they did not have the facilities to separate the football players from the other students like most major universities so the players were assigned to dorms with other students so Kevin became my dorm mate my junior year. Kevin was black, stood five eleven, his hair was braided in short dread locks that came down to touch the back of his neck and just over his ears, his body was well toned and athletic and muscular but not the bulging muscles of a body builder but more like a very well-toned swimmer. Kevin was very good looking and even a straight guy like me had to appreciate his looks and well-toned body.

Kevin was also very nice and while nervous at first at having a good looking, athletic, masculine roommate and me being on the feminine side and thin and short he put me at ease quickly. He never teased me about my girlish looks or mannerisms or even the way I giggle like a girl at his jokes or comments even when I would blush but listen intensely to the stores he told me of his sexual adventures while at college. Kevin had no problem getting girls but never brought any to the dorm. We became even closer after the football season when he was in the dorm more often and I helped him with the classes he struggled a little in. We even double dated often and Kevin dated two different girls as he accompanied me and Jennifer to dinner or the movies. It was easy to see he was not into being committed with either of them. Jennifer liked Kevin also and enjoyed his company and thought he was a nice young man she would tell me. Kevin would tell me how lucky was to have a girlfriend as pretty and sexy as Jennifer and seemed very shocked when I confided in him that Jennifer and I had not had sex even after so many years of being her boyfriend. Jennifer had given me many blow jobs over the years since we first became sexually active with one another but we had yet to go take it to the next level; her telling me she wanted to wait until we got married after college. We were not officially engaged but we both knew we were going to marry one another after we graduated and started careers.

Kevin would masturbate at times during the night when he thought I was asleep, heck that was not odd I mean I masturbated also but just not with Kevin in the bed next to me only a few feet away. What was really odd at least in my eyes was I would watch him. I would pretend to be asleep as he pulled the sheets off his body, pull down his underwear, and jerk off using his own saliva as a lubricant and watch him. The dimmed light from our window through the curtains gave me a perfect view of his cock. The first time I saw him I was surprised at his size.

In surprise I mean it was not as large as I would have expected. I was not much into watching porn but like all guys yes I had been curious about pornography and seen some and it was so easy to access on the internet; what would have surprised most of mine and Jennifer's friends was that the majority of the porn I watched was with her. It was not like we watched porn constantly but on occasion when alone in her dorm room or in mine and after making out for a long period of time she would suggest we watch a little to get more aroused before she gave me a blow job and the majority of the porn she put into the search engine was interracial porn with black men fucking white girls. So watching that genre of porn I bought into the stereotype that black men had very large penises. That was not to say Kevin was not largely endowed, but not as large as I expected even though he was certainly larger than my six inch, thin penis. Kevin's cock looked to be about eight inches long and thick.

I would watch Kevin masturbate and it turned me on a great deal seeing his larger penis, listening to his masculine grunts he tried his best to muffle, and then watching his cum explode from his cock. My own small penis would be rock hard by the time he was done and I would wait until I thought he was asleep, go into the bathroom we had in our dorm room, and masturbate myself. I would always start with imagining Jennifer standing in front of me in just her panties, which was as far as I had even seen her naked, but my thoughts always uncontrollably turn back to Kevin's cock and I would have an orgasm with the image of him jerking off in my head.

It was one night after our winter break and football season was over and once again I was watching Kevin masturbate when he suddenly stopped and turned his head to my bed.

"Nate." Kevin said in an almost whisper.

I shut my eyes and pretended to be asleep. I thought he may have thought he was caught and I did not want to embarrass him.

"Nate." Kevin said again, this time louder. "Nate." He repeated even louder.

I slowly opened my eyes and looked over and saw he was now sitting up in his bed on the side and his feet on the floor but he had not pulled up his underwear and his cock was standing up between his legs.

"Ummm...Kevin...what's wrong?" I asked as I feigned just waking up.

Kevin chuckled, "You can stop pretending. I know you were watching me."

"Wa...wa...watching you? What do you mean? You just woke me up." I stammered out embarrassed.

Kevin chuckled, "Cut the bull shit, Nate. I have known for some time you like watching me jerk off."

"I...I...I don't know what you mean." I said in a scared voice.

I was frightened, not that Kevin would hurt me, but that he would tell people and it word would spread over campus Jennifer would find out.

"I don't care if you watch, Nate." Kevin added in a kind deep voice. "I don't care at all and I like that you watch me. Turns me on actually. Matter of fact what don't you come here so you can get a better view."

"Kevin!" I cried out softly. "I...no...I...well...no...I just can't." I protested weakly and found myself staring at his muscular chest and down to his larger, well-shaped penis.

Kevin smiled, "Yes you can. I won't tell anyone and I know you won't. Get out of bed and come sit next to me." He patted the bed to the left of his body. "Plus you know you want to get a better look at my cock."

"Just...just...promise you won't tell anyone?" I asked.

Kevin was right, I wanted to get a closer view of his penis and watching him masturbate and my own small penis was very hard as I admired his body. Kevin nodded his head in promise not to tell anyone.

While Kevin slept in just his boxer briefs I slept in a tee shirt and men's brief underwear and when I got out of bed my hands dropped down to cover my erect penis pressing against the cotton on my briefs. Kevin smiled at me.

"Come sit here." He said and once again patted the bed and then reached over and turned on the small lamp on his nightstand.

I swallowed hard, my eyes still on his body and penis, and walked slowly to his bed and sat down next to him. Kevin grinned and put his arm around my thin shoulders and pulled me closer to him and now my skinny, alabaster toned thigh was touching his black muscular thighs. I felt a sudden surge of lust and desire pass through me when we touched.

"Don't sit so far away." He said when he pulled me close and kept his arms around me.

Kevin reached over and put his other hand on my upper thigh and started to caress it gentle but with a masculine touch. I once again swallowed hard but this time not in nervousness but in sexual desire. My eyes kept darting between his hand caressing my thigh to his hard penis, which seemed larger up close. Kevin was talking as my head seemed to become dizzy and I had to make myself focus on his words.

"...I like both men and women, Nate." Kevin was telling me. "I like white girls and white boys, but I only like sissy twink gay guys like you."

"I...I...I am not gay." I protested softly.

Kevin chuckled, "Well you certainly are at least bi sexual by the way you are reacting to sitting this close to me and looking at my cock."

Kevin moved his hand off my thigh and put it gently on my chin and moved my head so I was looking into his eyes causing me to give a girlish whimper.

"Fuck you are pretty. You are by far the prettiest twink I ever saw...damn you are prettier than most girls on campus. The sexiest femboy I ever met."

"Tha...thanks I guess." I stammered out looking into his dark eyes and handsome face. I knew what the term "twink" and "femboy" meant' I had been called those names often. Yes I knew I was an effeminate young man and had feminine looks and body type and been teased about it for years, but the way Kevin called me those names it was not in insult but as a compliment and for the first time being called twink and femboy made me feel good.

Kevin then leaned in and I knew he was going to kiss me and I surprised myself by not pulling back but instead closed my eyes, parted my lips slightly and leaned in to meet his mouth with mine. When our lips met I made a girlish whimper as Kevin's tongue found its way pas my lips and I replied by opening my mouth wider to allow him access and ran my own tongue over his. I was surprised how gentle his kissing as; masculine most definitely but also gentle. I guess I expected his kissing to be rough and furious or something; I really did not know what to expect since he was the first male I ever kissed. What I did know was how kissing him and feeling his hand run and down my thigh as he caressed me when we kissed; it was very arousing and exciting and like being shocked with a lasting pleasant jolt of electricity. I got very aroused when Jennifer and I made out but nothing like this. Kissing him and being held in his strong arm as he caressed my thigh made me feel so weak and feminine and I found the feeling extremely pleasant. When I made out with Jennifer it aroused me and I got sexual excited but the excitement I felt having Kevin kiss me and caress me and the feel of his strong arm around me was incredible; I wanted him to push me back on the bed, get on top of me, and kiss me more so I could wrap my thin arms around his larger body and feel him grind against my pelvis and very hard penis as he kissed me. That however was not what he wanted.

Kevin brought his hand to my face and gently caressed my cheek as he brushed my black hair behind my ear and started kissing my neck causing me to moan out loudly. My hair was cut medium length for a boy, the sides came down over my ears, the back past the nape of my neck, and my bands were long and styles to swoop to the side giving me an "emo" look. It was a hair style Jennifer suggested I have while I thought it gave me even more of a feminine look she liked it a great deal. I even told her I was trying to lose the girlish look and she just smiled kindly and kissed me and told me she liked that I was a pretty feminine looking boy and would not have it any other way. Naturally I conceded to her as I always did.

As Kevin kissed my neck and even ran his tongue over my ear I wrapped one arm around his waist and was whimpering and moaning in desire and then Kevin took my hand and moved it to his crotch.

"Touch my cock, Nate." He whispered in my ear.

I did not resist or try to pull away but instead placed my small hand around his cock and gave it a gentle squeeze to feel the size and hardness of him. Kevin moaned out as I started to stroke his cock slowly and his masculine moans aroused me even more. As he continued to kiss my neck I opened my eyes and watched as I ran my hand up and down his thick shaft and the sight of my small hand on his large penis was amazing. I never felt such sexual excitement as I did while Kevin kissed my neck passionately as I stroked his wonderful penis.

"Suck it, Nate." Kevin whispered in my ear once more. "Put your mouth on it."

I pulled back and looked into his eyes but still hand my small hand wrapped around his penis and seemed to not be able to let go of it.

"I...I never done anything like that, Kevin. I...I don't know how." I said in a whisper, my natural falsetto voice came out. I normally tried to talk in a deeper more masculine voice, well as much as I was able to; but my natural voice was much more feminine than it should be for a male. Due to my excited state my natural voice came out.

"It's easy." Kevin said in a reassuring voice. "Just do what Jennifer does to you when she sucks your cock. You will get the hang of it soon enough."

I looked at his penis again as my hand still moved up and down the shaft slowly and I could see the small amount of clear pre-cum on the head; I never felt the urge to protest and tell Kevin I did not want to give him a blow job because that would be a lie. I did want to feel him in my mouth and my nervousness came from not knowing how to do it and the thought if I could since he was much larger than me. When Jennifer gave me oral sex she said sometimes it was difficult for her to put all of me in her mouth and Kevin was much larger than me. I wanted to please him in that manner but was nervous that I could not.