My Story Pt. 01

I was recently reading the comments left by readers for "A Cuckold Made" by Everyonesavoyeur, which is very well written by the way. I like reading the comments because this is where you find tidbits of people's real stories, which I find extremely hot. As I was reading the comments of this particular story, I found many comments that I could relate to. I would actually say to myself, "that is me" or "I do that" after reading a comment. As I really get off on reading real life stories, these comments inspired me to write my own story based on real events. See I'm a cuckold sissy. There, I said it aloud, well sort of. I might add I'm a very happily married cuckold sissy and I love my life. It is perfect for me as I get to live out my fantasies and explore all my sexual desires.

But how to tell the story of how I went from a normal teenage boy to become a cuckold sissy. As I thought about it, I determined that my life is best explained in phases. Now, some of these phases overlap, but they are generally consecutive. The first phase was my "normal" phase of growing up as a perfectly normal heterosexual male prior to the age of 18, which I will not cover as a separate phase. Any background information that I think is needed to tell the story from this first phase will be provided in the appropriate phase.

As this is a story of my life, it may not be as well written as some of the fantasy stories, but I will attempt to write enough detail to convey my emotions, feelings and arousal as I recall my memories. The later phases have more detail because; A) they have occurred more recently than the early phases and one tends to forget details as time passes; B) The later phases have much stronger emotions associated with them, and these emotions make memories easier to recall - like when you hear a song that was popular when you were in high school, you remember things you haven't thought about in years.

The Awakening Phase:

My awakening phase took place shortly after I turned 18 while still a senior in high school. The name of this phase has a double meaning that you may pick up on later, if I have to explain it to you, it just loses something. I grew up on a farm in the Midwest, and as with many Midwest families, mine was a rather big family. I had a very normal life growing up. Well normal for a farm boy who went to catholic school, that started with church every day. That just makes my "fall" from "grace" all that much further, and less probable than one would think. My best friend growing up was a kid that lived on the farm just a little way down the road from me. He was a lot like me, my age, came from a big family and went to the same school as me, and he just so happens to be my cousin. He will play a pivotal role in this phase.

When I was a junior in high school, my family took the big step and moved from the farm to a city several hours away. When I was a senior in high school, I went back to visit my old school and my best friend, whom I stayed with. The first night we were up talking about girls, like guys do. Neither one of us had much experience, other than some making out and heavy petting. But he did tell me our cousin, who was hotter than hell and also a senior at his school, was pregnant. Apparently, she had more experience than we did.

We went to bed that night, sharing the same bed, which was very normal when you grew up in large families, you were always sharing your bed with a brother or friend. Shortly after I fell asleep, I woke up. I had been sleeping on my back and my friend had his hand in my shorts and was playing with my cock. I was already hard. I didn't know what to do, but since I was apparently somewhat enjoying it, I just pretended to be asleep. He really like playing with my pubic hair and would run his fingers through it as he was stroking me. He eventually pulled my underwear down and I noticed he had pulled his underwear down also and he would rub his hard cock up against me. He then put his mouth on my cock. He never kept it there long, but he would tentatively suck it a bit. I can't explain why I wasn't freaked out, but instead I was actually enjoying it and had no intent on stopping him. This went on for some time until he eventually pulled my underwear back up and we both went to sleep. Not sure how I went back to sleep after that, but I think I did so rather quickly.

The next day I accompanied my friend to school to see my old classmates. I had a great time reconnecting with my friends. The day was pretty normal, and I never let on to my friend that anything had happened between us the night before.

We went to bed the second night, just like the night before. I can't recall if I thought about what might happen once I did go to sleep, or if I wanted something to happen or not, but went to sleep I did. Once again, shortly after falling asleep, I was awakened by my friend playing with my cock. As the night before I was rock hard and feigned sleep. He pretty much repeated to me what he had done with me the night before. I was "asleep" on my back again, and at one point he whispered in my ear, "roll over honey". Him calling me honey really turned me on, and being the submissive person I am, I rolled over on my side and put my back to him. He then proceeded to stick his cock in the crack of my ass and rub it up and down. He would also point the tip of his cock at my rosebud and hold it there.

I was so hot and horny at this time that I couldn't feign sleep any longer. I reached around and grabbed his cock and my hand and started stroking him. He froze for a minute, but as I kept stroking him, he relaxed. It was my turn to tell him to rollover and he rolled over on his stomach. I immediately mounted him and let my cock slide up and down the crack of his ass. I dry fucked him for a minute or two until I came in the crack of his ass. I then rolled off him and I heard him pull up his underwear, my cum still in crack of his ass. Not a word was said and we went to sleep.

The one regret I have to this day is that I never got my friend off. I wish I had sucked his cock or jerked him off to an orgasm, but I didn't. I wish I had done so much more with him that night. I never imagined that my first "sexual" experience with another person would be with a guy and not a girl, but it turned out that way.

Nothing was said the next day about what we did the night before. In fact, nothing was ever said between the two of us of what happened that night. I'm sure my friend doesn't realize that experience "turned me into" being bisexual. I'm actually glad it did, as it has opened up a whole new avenue of sexual pleasure to me. I'm sure there are many others out there like me, who were exposed to a bisexual experience that made them bisexual in return. I remember chatting with a guy in a chat room once, he had considered himself to be straight, but after a drunken night when a bisexual friend of his talked him into letting him suck his cock, he was hooked. Said it was the best sexual experience of his life. So, I'm sure there are many other straight guys out there that are still straight, only because they haven't become awakened, yet.

My interest in men at the start was purely sexual, not romantic. I was not interested in making out with a guy or cuddling with them, it was all about their cock. I wanted to suck it or have them fuck me with it. But as the years went on, that slowly changed. I started thinking of being with a man, having him kiss me, being in his arms as we slept together, him making love to me, not just fucking me. By the time I had my first actual sexual experience with a man, I was all in. It would be quite a few years after this before I this would occur, but I will cover that later. I still have a couple of phases to go through before I get there.

The Cross-Dressing Phase:

I'm not sure how this phase of my life started or why. It could be that as I started to explore my bisexual feelings, I started introducing anal play into my masturbation sessions. I liked the feeling of a make-shift dildo inside of me. I also realized I saw myself as a submissive bottom. I wanted to suck the guy's cock and I wanted the guy to fuck me. As a submissive bottom, I guess the next logical step was to cross-dress like a girl, it was for me anyways. I remember the first time I did I was house sitting for the neighbors across the street. I got daring one day and rummaged through the wife's lingerie drawer and found a silk teddy. I stripped and slipped the teddy on and got hard immediately. I had a wonderful masturbation session and got myself off quickly. That is all it took to hook me on cross-dressing, much like becoming bisexual, one time is all it took. I eventually stole that teddy and it became the first piece in my pleasure trove.

As the years went on, I bought more and more of my own lingerie. I loved buying panties, the sexier and more feminine the better. If I walk by the panties section in a dept store and see a sexy pair of panties, I have to have them. I have way more panties than any one person needs, but panties are a fetish of mine. I eventually added bras, hosiery, nighties, dresses, skirts, blouses (silky ones of course) and shoes to my collection. It was slow at first, but it gained momentum as I got older and braver.

This phase could also have been called the cross-dressing cum-eating phase, as it was during this phase that I gained a liking for eating/drinking my own cum. At first I was only attracted to eating my cum when I was in the height of sexual arousal, right before I was about to cum or when I was cumming. After I came, I no longer was interested in eating my cum. So, I would get inventive on how I could have my cum and eat it too. Sometimes I would cum in a shot glass or condom on my first session of the night, then an hour or so later, I would masturbate again, then during the peak arousal period, I would drink the cum from the shot glass or suck it out of the condom. Other times I would bend my legs way behind me while on my back and point my cock at my mouth as I came. It was so hot eating my own cum, I absolutely loved it, and the anticipation of eating my cum always added to the strength of my orgasms. As time went on, I developed the taste for cum at any time. I eventually would enjoy eating my cum as soon as I was done with my orgasm.

I still hadn't had my first experience with a guy yet, but I knew I wanted him to cum in my mouth when I did. I've never understood women you don't swallow cum. I never let an ounce of good cum go to waste, and all cum is good.

Dating and Marriage Phase:

It is important to remember, during my dating and early marriage phase, I was 67% heterosexual and 33% bisexual. My interest in men was not romantic, it was purely sexual at this time. I was attracted to women both sexually and romantically. Pretty women turned my head, not good-looking guys. So, I dated girls in high school and college like any other "normal" person. I didn't lose my virginity with a girl until my freshman year in college. I had a long term on-again off-again relationship with a good catholic girl late in my sophomore year of college through the remaining of my college years. So, I wasn't getting much sex there, but during a couple of the off-again periods I hooked up with one of the girls in my fraternity's sister sorority.

I met the woman that I would eventually marry my third year out of college. I had taken some MBA classes mainly to meet women and I saw her in the class. My roommate at the time went to college with her and we met her at a bar, along with one of her friends. We started dating shortly afterwards. Once we started dating, we spent every day together. Within six months we were engaged, and a year later we were married.

A little side note about the two of us. I realize I haven't told you my name yet, or anything physically about me. I'm Roland and I'm 5' 10" and weigh 140 lbs. My wife's name is Maria and is 5' 6" and has weighed 115 lbs since she was in high school. We are both on the smaller frame size. I definitely married up, and all my friends agree. My wife is better looking than me, and although we made about the same amount of money when we got married, she started to climb the corporate ladder and was making more than double what I made within a few short years.

Our sex life was good, but I would not say it was great. I am average in the cock size, both length and width. Do I wish my cock was bigger, of course I do, I think every guy wishes his cock size was a bit bigger. Maria has what I call barely B size breast, which I'm sure she would like to be bigger, but my motto is more than a handful (or mouthful) is just waste, so I am fine with her breast size.

My more pressing problem was I am a premature ejaculator, especially in my younger years. Once I enter a woman, I'm ejaculating within the first minute. Something about that warm, wet, soft tunnel engulfing my cock sets my off. Luckily for me back then, I would stay hard after cumming. I would have to slow down for a bit, as the tip of my dick is very sensitive at this point, but I could continue to have sex and then cum again. I don't think most women I was with realized I had orgasmed that fast. I had one girl I dated comment on how long I lasted before I came. In reality, I came in her two or three times during that timeframe.

Maria on the other hand confided in me early that she usually cannot reach orgasm with a man inside her. She had only dated one person that could make her cum while inside her. For her to orgasm she needed the cock rubbing on the outside her, on her clitoris. So much of our sex was what I came to know as outercourse, vs intercourse. I enjoyed that also, as I could last a bit longer this way, but on the downside, there was no way to hide when I did orgasm. I did learn that masturbating in-between our love making sessions did allow me to last longer.

The upside of outercourse was the pressure and friction on my cock caused by our two bodies felt good and produced some powerful orgasms on both our parts. Sometimes, if I was at a slight angle on top of my wife, the tip of my cock would be poking out between our bodies, and when I came, my cum with shoot and hit her tits and sometimes in the face. My wife always claimed size didn't matter to her, but when I asked her about the guy that could make her orgasm while inside her, she did admit he was thicker than anyone else she had been with, which wasn't a lot of guys. So, length didn't matter to her, but width apparently did. She probably needed the extra thickness to stimulate her clitoris.

At the time we got married, I had only amassed a small collection of women lingerie and panties. I kept these hid away and out of site. But now that my heterosexual side was satisfied, by bisexual side started to get stronger, this is when I started buying more and more women apparel, bras, dresses, skirts, silk blouses, nighties and panties of course. I even bought my first dildo. As my collection increased, I stored them away in a locked trunk in a crawl space off the master closet. When Maria was out of town I would bring out the lingerie and start fantasizing about being with a man. I would practice giving head to the dildo and even learned to deep throat it. The act of giving head, even to a dildo, made me hard as a rock. And when I would put the dildo in my ass, I would cum very quickly. I would try to control myself, as I liked the feeling of the dildo inside me, but apparently having a cock in my warm, wet, soft tunnel had the same effect on me as if I was inside a woman.

Cuckhold Phase:

So how did I start fantasizing of becoming a cuckhold, as it was all me at first that wanted to be a cuckold. Like everything else in my life up until now, it came down to exposure. I used to read Penthouse Letters as my porn of choice. I'm not much into pictures or video porn, to me it is all cerebral, I like stories, hence why I'm now a Literotica fan. And the stories I found that I liked the most, other than the few gay stories they would throw in, were in the categories they called "Someone's Watching", which was usually the husband hiding in the closet watching his wife being taken, and the other was "Take her, She's mine", which were the more open cuckold stories. For some reason I was really drawn to these stories. I usually could get through only one story before cumming. Some of the longer stories I would cum multiple times before I could get through it. The stories that I particularly liked, I would tear out of the magazine and put into the before mentioned trunk with my cross-dressing apparel.

A couple of years into our marriage, I started bringing my cuckold fantasies into our love making. I started talking to her as if she was fucking someone else and not me. I would ask her what she liked about the guy that was fucking her. Or when she came home late from work, or being out with the girls, I would ask her to tell me about her date with her lover and what they did. We always ended up in bed with her going into great detail describing how her lover fucked her as we were having sex. She eventually got into it and would instigate it by saying we had to hurry, her husband was going to home soon, which always got me off quickly.

If we happened to be doing intercourse, and not outercourse, she would tell me (as her lover) I had to pull out, that I couldn't cum inside her, that she only allowed her husband to cum inside her. I would then tell her I was going to cum inside her, and she would feign trying to keep me from cumming inside of her. This really got us going when I came inside her she would actually get off too, as this played into her rape fantasy that we would occasionally act out (and you thought I was kinky).

I tried not to overdue the cuckold fantasy play with her, but I couldn't help myself sometimes, it just got me going like there was no tomorrow. One day she called me out on it. She wanted to know if it was just bedroom banter, or was I really wanting her to take a lover. I came clean (on this anyways, I still had not told her about my bisexual side or my cross-dressing) and told her it was more than just a fantasy for me, that I actually would find it exciting if she had a lover or lovers.

Now that I look back on it, we didn't hardly discuss it. She did ask about whether I would be jealous or not. I told her I would be way too aroused to be jealous. I told her I had one request though, that she tell me every time she was with another guy and every detail of their encounter when she came back to me. That was it, she asked, I said yes, the decision had been made. I was a bit selfish; I didn't ask her what she wanted, I only cared she was willing. And I have to say, I was pleasantly surprised that she was willing, and that we reached an understanding so quickly.

Although the decision was made quickly, it didn't happen quickly. Being out of the dating seen for several years, my wife had to get back into it. She did some looking online, something she had not done before, she started hanging out with her single friends who she would accompany to bars (she was there to meet potential guys that she could contact later when her friends weren't around). It was a bit weird watching my wife trying to find guys to date. I made sure she knew I was excited that she was pursuing this, but let her pursue it in her own way.

She eventually got comfortable with a few men she met online and had met at the bar that she accepted dates with several of them. I would talk with her as she was getting ready to go out. She would even ask me what I thought the outfit she had on; was it appropriately sexy, without being slutty. I freely gave her my advice. I liked how we were into this together. Then she would go off on her date. Luckily, we lived in a large enough city that she wasn't going to run into someone we knew when she was out.