Joanna kissed her way down his sculpted and perspiring torso, stealing a taste from each of his six abs, while gently caressing his hard throbbing cock through his faded Levi's…  Joanna is Rob’s better half. Unfortunately, Joanna is trapped within Rob and can never fully express herself the way he or she wants. She is a beautiful brunette with the perfect hourglass figure. She has an angelic face, not overly large up top, but definitely noticeable with wide childbearing hips and a nice bubble butt. Her legs are long and slender.   

Rob on the other hand is shy with average looks. He sees himself as being undesirable so he doesn’t put himself out there. While looking in a mirror all he can see is someone who will never know what it is like to love or be loved.  

When he looks at himself, on the inside all he sees is Joanna.

I have been cross dressing pretty much my whole life, but up until this story takes place, I hadn’t known that I would like anyone who wasn’t a female. This story takes place back when I was 18 and was a freshman in college.

Stating myself as being a cross dresser doesn’t really tell you who I am, it is much more than clothing. My first time with cross dressing is a story in itself. From the inside I feel like a cross dresser when I wear guy clothes.

Upon entering college, which was a couple of hours south of where I grew up, I began by getting enrolled to live in one of the on Campus Dorms. It was in the dorm that I became friends with Thomas. He was 6'9", a sophomore, and very good looking.

Thomas was outgoing, always taking the chance to talk to others. He was the complete opposite to me.

I was shy, tended to crawl into a shell and kept to myself. Being the loner in the dorm seemed to put a target on my back for harassment from upper classmen.

One day I was climbing the stairs to get up to my room, and Todd and his two goons came running down the steps and knocked my books and notepads out of my hands down the stairs.

This really tall guy saw what had happened, picked up parts of my things for me and handed them to me. Thomas introduced himself, and told me he hoped to see me around later. I didn’t run into him again until a week later.

I hated living in the dormitory; my room that I shared was on the fourth level, at the east end of the corridor. The outside of the dormitory was the typical old historical brick building, with a spacious green lawn with tall oak trees to provide shady areas. The inside was not much to speak about, twenty four rooms on each of the five floors and two students per room.

My room was a twenty-by-twenty foot box with two twin beds, two chest of drawers, two small desks, two small closets, and one common bath room. Well make that a half bath, a sink and a toilet. For showers, those were on the West end of the corridor. One large room with twelve shower heads, six on each side.

Being picked on constantly, I tended to get up early and shower before anyone else woke up. One morning I woke up late and had to shower with others. While washing my face, someone poured a large pool of shampoo directly below my feet. Of course I stepped in it and fell. I landed hard bumping my head on the floor. It hurt, but what hurt worse was being picked on, embarrassed, humiliated…

I couldn’t help it and began to cry. It was Thomas who came in and saw what transpired, helped me up and pretty much ran the others off. I rinsed off, and spent the day in my room skipping classes.

Thomas came to check on me after his classes, he could tell I had cried most of the day. He invited me to dinner, I declined. Then he pretty much dragged me out of the room and forced me to go to dinner with him. At dinner, he told me I would not have to worry about Todd or his friends as they would not be bothering me again.

That first semester, I damn near flunked out of college.

The reasons for my awkwardness and being in a shell, I never felt comfortable socially. Back in High School I was the tallest person in the school at 6’4", and the closest anyone was to me was around 5’10”. This made me feel very awkward, as I didn’t feel like I fit in with any of the groups. Another reason for my awkwardness was that I felt like I was a girl.

I didn’t like hanging out with the guys and I was jealous of the girls.

Thomas being taller than me, made me feel like I was average in height, when we were out I felt like I was part of the group and some of my awkwardness disappeared. I was still somewhat awkward, due to being a girl and all.

It was with Thomas that I discovered porn magazines and videos. It was after being in the adult store with Thomas that I went back one night by myself. I ended up in the video arcade, watching those twenty channel TV screens. I was scanning through the channels, when I noticed a she-male who was sucking a large cock. I was mesmerized and excited and it made me really horny. I also saw a video with two girls and another with two guys. I knew there were gay people, but it was the first time I saw it and it looked so hot to me.

Back at the dorm, that night I was laying in bed, I started thinking about how hot it looked with the two guys, it was really a middle aged man and young man, and how pleased the submissive man looked as he was giving head and later on the receiving anal.

I feel asleep thinking about what it would be like to be the submissive guy in a gay relationship or what it would feel like being a woman.

After the first semester, Thomas asked me if I wanted to find a two bedroom apartment and split the rent. A long story short that is what we did. Thomas took the master suite as he had a better job than I did, and he paid a little more than half.

When school settled in again, we got into a routine. I would normally take care of most of the cleaning, although cleaning the toilet we split it where he would do it one week, and then I would the next time. We each also had to keep our own room clean. I would clean the kitchen and the rest of the apartment. I really didn’t mind, as I love having a clean home and it gives me satisfaction whenever I would come home and the place smells good.

Living with Thomas in a private setting; I became a much happier person. Thomas and I became close friends, spending a lot of time together.

Now that I had my own room, I started collecting a few female items of clothing that I kept stored in a plastic bin beneath the bed. Whenever I was in my room studying, I would have on panties, a bra, stockings and a garter belt, under my male clothes. I would go further if Thomas was on a date or just out studying. Being able to dress more was giving me good feelings, but at the time I still never connected that I was much happier when wearing female garments.

Sometime around mid-term, I was in the living room studying on a Friday night. I had on a pair of light blue nylon panties, underneath my sweatpants. I was in a very girlish mood as I was getting caught up reading some poems that I had to study and answer questions about.

I love poetry; I just wish that I could write them. Anyway, Thomas was in the shower and we were planning on going out that night. We were getting to be very comfortable around each other, and he came down the hallway with a towel around his waist to get a drink. I happened to look up at just that moment….

Thomas’ towel came undone and fell to the floor just as I was looking. It was the first time I ever really took notice of another guy’s penis. I think I bit my bottom lip as I was looking at him. I could not stop looking either. It was lovely, about 6 inches soft and hanging there pointing to the floor.

The difference between Thomas and myself, I have a thingy at least that is what I called it back then. Thomas had a cock. When mine is flaccid it actually goes into hiding. At this point all I knew was his flaccid was longer than mine hard. It is really okay with me, as I really wish that I didn’t have what I have.

Well Thomas left the room, and went to get dressed, I couldn’t concentrate, my face was flushed, and I was embarrassed. I sat there for a bit, then decided to go shower.

When we left, not much was said between us until we arrived at the 1 st bar of the night and had a couple of drinks. Luckily for me the talk went nowhere around the subject of what had happened. After an hour or so, the first bar nothing was happening so we decided to try another one.

At the second bar we ran into some guys we know and partied for a bit. Thomas ended up dancing with a couple of girls, I never did ask anyone. My mind was still on the same topic that I was thinking of ever since that 1 st time of seeing the gay porn, and also what I had seen earlier.

As I sat there and watched Thomas dancing with a girl, I started feeling jealous of the girl and wishing I could be in her shoes. What would it feel like to be in his arms, or with him hugging me, or kissing me?

A while later we were both sitting at a table and drinking but had seemed to run out of things to chat about. Thomas spoke, “You seemed like you wanted my dick earlier”.

Wow, talk about an opening to a conversation. I immediately felt that flushed feeling again, my face must have turned ten different shades of red from the embarrassment, and I felt like I could feint at any second.

I wanted to say to him, “God, yes I want it and you." I couldn’t speak. If I had tried, I am sure gibberish would have come out. I was wishing he would just pick me up in his arms and carry me home, but I sat there like a paralyzed mute. Thomas even said he was open to trying some things if I was.

I was scared to say yes. In the back of my mind, I was wondering if he was trying to get me to say something and then use it against me. Like guys do all the time, to joke around with other guys. I ran through a quick scenario. Yes I would like that. Then the next time we were sitting around with others he could put it out there…

Hey everyone, Rob wants my dick; he told me that the other day.

I should have known better, that we were really good friends and that I could have trusted him, but I continued to try and swallow my tongue every time I wanted to speak. Thomas changed the subject and after another drink I found I could speak again, but we were on to another subject.

We ended up back at the apartment, retiring to our own rooms. That night I slept in a yellow nylon tricot nightgown and thought about what it would be like to be in Thomas’ arms being made love to.

The next day nothing about the topic was mentioned by either of us, but I did notice my eyes always went to his crotch trying to catch a glimpse of the outline of his cock. I think Thomas noticed me looking a few times, but had the decent demeanor not to embarrass me.

That night, being a Saturday we went out again on the premise of partying and to pick up girls. The first bar was pretty good, some really good looking girls, but neither of us seemed to be interested. At least I wasn’t.

We made small talk for awhile, talking about our schools sports teams etc. I played sports when I was in high school, but only because it was expected of me. I really didn’t care a lot for it, especially the grueling practice sessions and having to get all sweaty. But growing up in a small town, you were in the sports group, or you were alone or you’d be included in the smoking and drug users group.

Okay, I got off topic there again. A little bit later, Thomas suggested that we try out a different bar. I agreed, so we left.

At the next bar, there was a good mixture of boys and girls. Thomas ended up hooking up with one of the girls, and after a bit he left with her. Hey great for him, I thought. Myself I finished my drink then left and walked around a bit till I ended up back in the adult theatre.

I watched some more of the gay porn and even ended up purchasing a gay novel. Then it was back to the apartment.

Thomas must have gone to her place I thought, so I striped out of my clothes. I grabbed some fresh panties, bra, nightgown, and some scented bubble bath soap and went to soak in the tub.

After my bath and getting my sleeping clothes on, I went to the kitchen and got a soda, then went to my bedroom. Just as I closed my bedroom door, Thomas and his girl came into the apartment, he laughing and her giggling.

Breathing a huge sigh of relief, I was relieved that I didn’t get discovered. I got into bed, covering up in case someone came in and lay in bed reading the gay novel I had purchased.

Thomas and his girl retired to his bedroom and keep me up most of the night. Hearing her moaning was beginning to upset me as my mind was again on the topic of me being in her shoes, wondering what it was like to be penetrated by Thomas.

It was a little weird to me, that I could only think of myself being with Thomas, and not just any faceless guy with a cock. I was like that though; I needed to feel some kind of connection with the person that my fantasy and desires were about.

Well sometime around 4am or so, with Thomas’ headboard banging against the wall, I started crying and finally cried myself to sleep.

On Sunday, I spent the day in the library, and during the week we studied. It was about three weeks later, that we were going out to party and just looking for whatever we could find.

We were walking down the strip, (6th Street, famous party street for the school I attended) a lot of the readers will know exactly what school it was. Anyhow, I wasn’t paying attention as my mind was still on Thomas. He suggested we try the place we were next to, so we went in.

It was dark, loud and people were dancing and having a very good time. I was so busy talking with Thomas and concentrating on our conversation that I didn’t notice the others around us. When our first drinks arrived, and we started drinking I started to look around and noticed girls dancing with girls and guy with guys, obviously we were in a gay night club.

I watched the different couples both girls and boys and noticed how happy they seemed to be. I wondered if I’d be just as happy if I were to be dancing with Thomas.

Once, Thomas and I were looking into each others’ eyes, me feeling like I was falling in love, he smiled. It was beginning to sink in; Thomas was having some of the same desires as I was.

Thomas spoke, “I know you want to make love to me."

For once, I surprised myself and smarted off with “I would never make love to someone before they danced with me."

I felt good about myself in that instance; I had finally stood up for myself and put the ball back into his court.

The ball didn’t stay there for long, sort of like one of those pitching nets you had when you were a kid and you didn’t have anyone to play catch with. You throw the ball hit the net and it immediately is coming back at you.

Well I must have been pretty close to that net because as soon as the ball left my hand it was back in my lap. Thomas had got up, came to my side of the table held out his hand and asked for my hand for a dance. I hesitantly gave it to him and he led me to the floor.

It was a slow song, and he immediately pulled me in close and there I was in the middle of a crowed dance floor, in the arms of the guy I wanted to be with. The more I thought of what was happening, we could have been at any other bar and Thomas could dance with any girl he wanted, instead he chose me. I lay my head on his chest and tears started flowing.

We danced to two more slow songs, and he never once took his arms from around me. We were slowly swaying turning every now and then, but we never really moved from the spot. I remember opening my eyes, a tear rolling down my cheek, and my eyes met with a girl, her head was on the shoulder of her girlfriend, and she smiled at me.

At the end of the third slow song, the band started playing some rock music, but we stayed in our embrace and continued to dance to the slow tune that I was still hearing in my head. In that moment, I truly felt like a girl dancing with her guy.

I don’t remember how long we danced; eventually Thomas parted from me slightly, with his hand lifted my head till I was looking in his eyes, leaned in and gave me a kiss. I felt all tingly inside, as if my legs were going to fail me. The first kiss was just a peck, then when were looking at each other, his eyes were saying beautiful things to me then he really kissed me. It felt like we French kissed for forever.

Once we broke off, he asked if I was ready to leave, and I was. I told him I wanted to go to the restroom. I was in such a daze, that I went directly into…

Yup, the ladies room. I didn’t notice the three girls at the mirror and dreamily went into a stall, sat down and relieved myself.

I had been peeing sitting like a girl ever since childhood. I never did like the urinals, they are gross. The only times I use urinals is when the men’s room is really messy and I don’t want to sit on the toilet other guys have peed on all night. Anyway I finished and went to the sink to wash, two of the girls were still there looking at me. I froze; I asked if it was me or them in the wrong room. They laughed and told me to finish and not to worry.

One of the girls happened to be the one who smiled at me when I was dancing. She made some small talk, introduced herself as Wendy. Her girlfriend was Trisha. Wendy asked me if that was my first time dancing with a guy. I told her yes. She told me I had the look of being in-love. She gave me her phone number and asked me to give her a call. I took it and put it in my pocket.

I met Thomas at the front door and we left. As we were walking he said he had to also go, but didn’t see me. I told him somehow I walked in and used the ladies room. We had a good laugh.

Once we had left 6th Street , and were walking back to the apartment, Thomas reached for and held my hand. He didn’t let go until we were inside our apartment.

Once the front door was closed we were back to kissing. This time he pulled me in close and his hands around my back, my hands behind his neck. It felt so good to be in this position, almost like being trapped, being trapped made me feel good, safe, and secure.

Thomas’s hands inched their way down to feel my butt which just caused my tongue to try and find his tonsils. Thomas broke the kiss and he took my hand and led me to his bedroom.

Once in the bedroom, he asked me if I was sure I wanted to do this, I nodded my head and he embraced me again and we kissed some more.

While kissing, he pulled my shirttail out of my pants, lifted my shirt breaking our kiss to remove it. He then began to play with my nipples while resuming the French kissing.

Thomas then unbuckled my belt and pants and pushed them and they fell to the floor. When his hand began to rub my butt, I remembered I had on a pair of rose colored nylon panties. It didn’t seem to faze him a bit. I was a little embarrassed, but what could I do. I stepped out of my pants and kicked them out of the way

Thomas removed his shirt and we went back to kissing and hugging. His warm chest against mine felt marvelous. The only thing that would have made it better would be if my tits were squashed up against his chest, but I didn’t have any so I got over it.

Thomas was never pushy with me, he never urged me to go down on him, letting me go about things at my own snails pace. I was just lost in dream land while we were kissing, with not a single care in the world.

I have no clue how long we had been there making out and all, but I finally broke away from kissing his mouth, and beginning to copy what and how Tracy proceeded.

Tracy is a girl from High School who I had a lot of first times with. She was beautiful and had given me my first kiss less than a year before. She was the first to fondle me down below, causing a volcano to erupt as soon as her fingers wrapped themselves around it.

She and I had lost our virginity to one another and I credit her for bringing me a little ways out of my shell. She was the first girl I ever loved, and the times with her could be a short novel.

Tracy gave me my first blowjob the summer before I left for college. I was sad that we didn’t have more time together, but she was younger than me and still had to finish high school.

I placed kisses on his neck using the tip of my tongue and lips. Then slowly made my way down stopping to suck and nibble on his nipples, then continued to kiss my way down his stomach until I was on my knees before him.

I love that position, like I am in complete submission to the man and am willing to do anything to please him.

I was kissing the crotch of his jeans as I was unbuckling his Levis . Once done with that chore I spread the crotch of the jeans and kissed his underwear as I slid his pants to the floor. Not once stopping the kissing until his jeans were off and it was time for his underwear. He was so sexy standing there before me in his white briefs and white socks.

I lowered his briefs, and was in awe of his penis. It was the most glorious and loveliest thing I had ever seen. Earlier I mentioned that flaccid he was 6” well not anymore he was hard as a steal bar and was at least 8” maybe more. I never measured it so who knows, but I do know it was over twice the size of mine.

I was thinking to myself, now how should I go about this. Well remembering Tracy again, I just did as she did on our first time doing this. I reached for his cock; softly wrapping my fingers around it. It felt hard and silky smooth and soft all at the same time.

I guess when you hold your own you don’t notice these things as all you feel is the hand touching your penis and not what the penis feels like.

I raised his cock up to his stomach, leaned in and breathed in his musky and manly scent. I became intoxicated with his smell.

Then I kissed each testicle and licked all over his balls for awhile, then traced my tongue upwards to the underside of the base of his cock. I lowered his cock letting go of it and placed my hands on his legs and slowly ran my tongue down the length all the way to the crown. I slowly made my way back to the base of his cock, wetting my tongue again and repeated the process on each side, top and bottom.

I backed away just enough to get right in front of his cock, leaned in slightly and placed a kiss right on the end of it. I placed several more of those kisses with each one getting longer until I opened my lips just to allow the head in, then right back out. I repeated that a second time while looking up into his eyes. He had a look of total submission to me.

I could not drag it out any longer, Tracy had continued the slow sensual blowjob for a long time, and I just gave in to my own lust, as I had to get as much of him into my mouth as possible.

I got him in till I started to gag, thinking, "Oh my God, I am going to ruin this moment."

Of all the porn I had watched, and when Tracy did this to me, I was the only one to gag. Little did I know the sound of a little gagging would actual sound hot to him. Tracy didn’t gag because mine didn’t reach her throat, the porn stars didn’t cause they have learned to control it. I didn’t know that and it worried me. Thomas eventually told me it sounded hot when I gagged and relaxing some I continued.

His cock felt hard, soft, spongy, smooth and silky all at the same time. After a few minutes I started to get a bitter and slightly salty taste, as his pre-cum started flowing. It didn’t taste too bad so I just continued. I had to pull off a few times as my jaw actually got a little sore, probably due to me trying to suck his balls out through the cock.

When I pulled off his cock a thin line of pre-cum and saliva went from the tip of his cock out to my lips. Thomas looked down and told me it looked very hot.

When I resumed sucking, it got better as I started to figure out you don’t have to suck so hard, and you can taste and feel more sensations in the mouth when not sucking so strongly.

He didn’t last much longer and before I knew it, before I had realized where this was leading, a blast of warm sticky cum hit the back of my throat. It happened so fast, I wasn’t expecting it; it surprised me to say the least.

I had never considered what I would do once it happened. The second shot was from me as my penis erupted in my panties as I had been rubbing myself.

As I continued erupting, I pulled off his cock just as a second stream came out, most going in, some getting on my lips, the third went across my nose into my left eye, the forth on my forehead and in my hair, and the fifth just under my nose and in my mouth and I figured out put the damn thing back in the mouth before this get out of hand.

That shit went everywhere! The one in the eye at first just blinded me, but it started to burn really bad. I ended up swallowing what was in my mouth, being as thick as it was; I had a difficult time getting it down.

I won’t tell you I fell in love with cum getting in my mouth, as I do think it is an acquired taste, but it wasn’t so bad that I didn’t want to do it again.

It all happened so fast that I could not comprehend what the taste was like in that moment, but I did feel pride that I was able to give Thomas so much satisfaction.

Thomas had me stand, and using a finger he wiped as much cum from my eye as he could, wiped cum from other areas, then led me to the bathroom and washed my face with a washcloth.

He then used close to a full bottle of Visine before the hurting stopped. We went back to his bed got in and laid side by side. As he was looking at me, we began to kiss some more. That is all we did, kiss and cuddle then he asked me what my feelings were about what had happened.

Other than cum in my eye, I had loved it all. I fell asleep in his arms.

The next morning, we woke up about the same time and he had the biggest morning boner. I went down on him for my second blowjob. I didn’t do the prolonged one like the night before, just got down there and took care of it. When he came I swallowed as it happened.

He got up and went to the bathroom, and I lay there thinking that I really like the feminine role, and no matter what happened with us, I’d never stop giving blowjobs.

I must have fallen asleep, as Thomas woke me and presented me with breakfast in bed. He couldn’t cook, so it was a bowl of Cereal, a peeled orange, and a glass of chocolate milk. I didn’t care what it was, just that he thought of me, and my eyes had tears again. He asked what was wrong and I told him nothing, that he had made me so happy.

After eating I went and showered, brushed my teeth and when I came out Thomas was lying on the bed naked. I joined him. We talked for a while; he asked me if I thought I was gay now and I told him probably bi-sexual, as I still like girls. I did mention though, that right now, and ever since the day I had seen him naked, he was the only one on my mind. With him, I was definitely gay.

Thomas kissed me, then made his way down, removed my panties and went down on me. I didn’t last long at all and it was over in about five minutes. When I came, he didn’t catch it in his mouth; he caught it in his hand and rubbed it on his penis. I remember thinking that it was cool that he wanted something from within me to be on his most intimate place.

He asked me if I trusted him, to which I replied absolutely. He lifted my legs to his shoulders, leaned down squashing my knees into my chest, and began to rub his cum lubricated cock on my anus, as we met in a sensual kiss.

I wasn’t so dumb now not to know what was about to happen, and I wanted it. As we kissed and he was rubbing me down below, I got so turned on I stopped the kiss and told him to fuck me.

OMFG, THAT HURT LIKE HELL! I just knew he split me in two, I would be found dead from a major blood loss. Probably my punishment for doing what I shouldn’t be doing.

How was I supposed to know, the porn stars all moaned and said how good it felt. Tracy had moaned and said if felt good. Were they all liars? In Thomas’ defense, he didn’t know, he had never entered anything other than a vagina.

To make it worse, I couldn’t even scream to let him know to stop as he had covered my mouth with his own, he had thought I was moaning in pleasure. After going in and out for five or so minutes he came inside me. He continued to slowly move in and out until he was too soft to continue. He pulled out and told me how great that had felt.

Then he noticed me crying. He asked what was wrong and once the pain became bearable and I stopped crying I told him.

He apologized over and over. Telling me it had felt so good that all he could think of was his pleasure. He had to help me get up; I could not sit on my tail. I went to the restroom, had trouble wiping the area as it hurt so bad.

Thomas came to the bathroom door and knocked, asking me if I was okay, I told him yes… and no. He said he didn’t want to alarm me, but there was some blood on the sheets. Again, my mind went to this big pool all over the place when it was not really that much. It still worried us both.

Thomas wanted to take me to the hospital. I said “Like hell!" No way was I going to explain “I am here because he fucked me in the ass." After getting off the toilet, I noticed blood on the toilet wipes. I washed and went to my room and put on a fresh pair of panties and a T-Shirt. I tried sitting on the bed, but it hurt too much.

Thomas was adamant that we had to call someone to make sure I would be okay. He suggested he could go out back to the bar we were at and ask for advice, thinking someone there may have had this happen. It was really a good idea, who other than the gay community would know better. I just didn’t want a bunch of guys knowing what happened. Then I remembered Wendy, the nice girl who gave me her number.

I told Thomas to look in my pants pocket from last night for her number. He found it and went and made the call. I heard him telling her what had happened, where we lived, and he hung up and said she would run by a drugstore and would be right over.

Well both Wendy and her girlfriend Trisha showed up. They gave Thomas a lip lashing, but told him he at least cared enough to call someone. I told them neither one of us knew this was going to happen and I have nothing to forgive him for as he did nothing wrong, other than kiss me while fucking so I couldn’t scream.

The girls laughed at that, and Wendy went to my room with me to inspect the damage. She was very good with what she did, rubbing a soothing ointment on and in my anus. There was blood on my panties, she called Trisha and asked her if she had a pad. She did and I received my first lesson on feminine pads. She placed it in a fresh pair of panties up a little higher in the back from where females wear them and had told me to put them on.

Wendy asked Trisha and Thomas to go back to the drug store and get me one of those inflatable donuts so I could sit on it. While they were gone, Wendy and I lay on the bed and talked. We quickly became friends in the forty-five minutes we had together.

She was one hundred percent lesbian, and I told her that I am probably bi-sexual. She asked about my panty wearing, and I told her I just preferred them over men’s, but if I had to I would wear men’s.

Wendy was shorter than Trisha at 5’10”. She had a lovely figure and I found out later her measurements were 36D-32-38. She had long curly blond hair. Trisha was six feet tall, with medium brown hair that fell to just below her shoulders. She had smaller boobs and was overall a skinny girl.

Wendy just had a way about her, in that I confessed everything to her so quickly. She told me she wanted to meet the female at some time. I was confused, and she said she wanted to see me dressed as a female. I told her that I didn’t have that much stuff, as I couldn’t dress in front of Thomas or anyone else. She told me once I was better, that we should meet at her place for a girl’s night.

Thomas and Trisha got back and with the donut cushion I was able to sit on the couch. The four of us all talked and became quite close friends. Wendy and Trisha suggested if we ever wanted to double date, they would like to join us, and even offered that if we were going to a non-gay event, Wendy could be my date and Trisha Thomas’ date. If you haven’t figured it out, Trisha was the man in theirs, as I was the woman in our relationship.

I skipped classes on Monday and by Tuesday I could sit without the donut, but it was still a little tender on the hard wooden chairs.

On Wednesday night, Thomas and Trisha went to a basketball game. Wendy had invited me over to her place. I went wearing a bra and panties under my jeans and t-shirt. Wendy made us some pasta and served white wine with it.

We talked a lot, I asked her about her relationship with Trisha. Wendy was deeply in love with Trisha, but she didn’t think Trisha was in love as much as she was. She also thought Trisha was bi-sexual and that something had happened to her so she had given up on guys. She would not tell me what had happened.

The discussion went towards my feminine feelings and before I knew it we were in Wendy’s room experimenting with makeup. She ended up doing it for me, explaining what she was doing. It would have looked much better had I had a wig, but it was still nice. I loved every minute that we spent together.

The discussion came back to me and my relationship with Thomas. I told her everything that had happened up to that point. She asked if I still wanted to be with him, and have sex with him. I told her yes if it could not hurt.

Wendy explained to me that I would have to prepare myself if I wanted to engage in sex. She told me that anal sex can be very pleasing and asked if she could properly introduce me to it, promising me I would not feel any pain. I agreed and she asked me to remove my clothes and lie on the bed.

We were both lying side by side talking when Wendy leaned over and kissed me. I gave her a questioning look, and she said “I love kissing girls." We kissed a little more, and then she asked me to lie on my stomach and relax.

Wendy got some KY from the nightstand, put some on her fingers and slowly began to caress my anus. She took her time and it was about fifteen minutes before one finger was used to penetrate me. After 10 minutes or so, she applied more lube and inserted a second finger.

Not once did I ever feel any pain or discomfort. In fact it was sensual, erotic and very pleasing. While she had two fingers in me she found my prostrate and gentle massaged it. It gave me an overwhelming sense that I was peeing. I mentioned this to Wendy, who told me it isn’t pee, but my semen was slowly being milked out. She said it is like a prolonged orgasm, so to just relax and let it happen.

Wendy rubbed me back there for about fifteen minutes then removed her fingers. She told me to stay still and keep my eyes closed. I heard her fumbling around in the nightstand then doing something. She started by kissing behind my ear, and she whispered, “Now I will introduce you to a girl’s best friend."

I felt a penetration; it was a stiff object she was inserting. It felt hard, cool, and smooth. She pushed it in then she was pulling it out. Back and forth she went and it felt so good. I wondered if it would ever feel this good with Thomas, then all of a sudden I felt vibrations and I had an explosive orgasm. The orgasm didn’t produce anymore fluids.

Once I finished, she pulled it out and showed it to me. It was a white plastic vibrator, about five inches long and less than an inch in diameter.

Wendy gave me the vibrator and told me to use it on myself every night for the next week, and invited me over for another Wednesday girl’s night.

I used it like she instructed, but I never had another orgasm from it.

On Friday night, Thomas and I went to a movie and dinner. For the last week, I got the impression that Thomas was still feeling guilty, so he was avoiding conversation. During the movie, I reached over and touched his penis through his pants. I left my hand there and lightly rubbed him.

Back at the apartment I gave him a blowjob swallowing all he had. While kissing afterwards, he rubbed me till I had an orgasm. Talking afterwards, he confessed that he wanted to make love to me, but didn’t know how to bring the subject up. I informed him that Wendy was teaching me how to prepare myself for him. He said that Trisha had mentioned that Wendy was helping and he was told to give me time.

The following Wednesday, Wendy and I ate out, and then went on a shopping expedition. We were in JC Penney’s looking at dresses. We found about three of them that looked like they would fit me. She folded the dresses in half, then draped them across her arm, added some men’s dress coats she had picked earlier. Handing me the pile, told me to try them on in the men’s dressing room.

Only one of them fit, but it allowed us to know what size, and we found one other dress.

For shoes, we both went in to a store. While she was being measured, when the sales lady left she pushed the ladies measuring device to me and we took a quick measurement. We ordered my size from a JC Penney’s catalog.

The next stop was Wal-Mart, choosing my own makeup. It was easy as everyone thought she was the one buying. The last stop was the adult store where we picked out a larger vibrator.

For the remainder of the week, I’d use the small vibrator, and then work up to the larger one. The first few times I inserted the larger one there was a little pain that would disappear shortly, then nothing but pleasure.

On Wednesday morning, I made an executive decision. After properly cleaning myself out, I lubed up real good and inserted the smallest vibrator, pulling up a tight pair of panties to hold it in place. After putting on a pair of jeans and a sweatshirt, with a bra underneath, I proceeded to my morning lectures.

It felt as if getting fucked all the way to class, then when sitting it would penetrate all the way in every now and then. I would shift in my seat to get some stimulation during the lecture.

Luckily, I was sitting on an isle seat. It was one of those theatre style lecture halls that have seats for a hundred or so students. Once when I shifted, somehow I accidentally turned the sucker on. The sound of the vibrations was light, I could feel it but I didn’t know if it could be heard.

I excused myself to walk quickly to the restroom. Can you imagine had I been in the middle of the row, having to squeeze by the other students with my buzzing butt in their faces? In the restroom, I removed the vibrator, took out the batteries, and re-inserted.

Let me tell you, if anyone ever wants to try this, make sure you take more lube. By the time the lecture was over and I made my way back to the apartment, it was getting a little annoying. I removed it for the remainder of the day.

On Wednesday evening, I picked up Chinese on the way to Wendy’s apartment. Once at her place, we put the food in the oven on warm. Wendy helped me to get dressed, assisted with my makeup, changed into dresses, and then we had dinner.

After dinner, we retired to her bedroom where we had a repeat of the other nights. After Wendy had used the small and medium size on me, she asked me if I would mind if she were to fuck me. I didn’t understand, so she asked me to wait as she would be right back.

A few minutes later Wendy returned naked with the exception she had strapped on a penis and told me to get in the doggy position. She slowly rubbed it in the crack of my ass. She slowly inserted and it was a little uncomfortable but started to feel good five minutes in. She would lightly bump my prostrate every now and then, and that felt marvelous. She went on working up her pace, it felt so good to just be in that position with no control over her movements.

We switched positions so I was on my back, my legs on her shoulders and she re-inserted. She grabbed my arms above my head and pressed her weight down so I had to just lie there submissively and let her do what she wanted. Most of the time I had my eyes closed enjoying the sensations I was feeling, but when I looked up at her, with her breasts hanging down, I made a mental note of how hot that looked and would one day need to be in the same position with a she-male.

Before she pulled out she banged into me pretty hard to show me how that felt. When she pulled out, she lay on me and made out with me. Wendy was the second girl I fell in love with. Even though I loved her, I knew her heart belonged to Trisha. Afterwards we lay there and talked.

I told her that I wanted to give her as much pleasure as she had given me. She told me not to worry, that Trisha would be there to take care of her after she returned from studying.

Wendy told me she thought that I was ready for Thomas. We got up, washed off our makeup, and I got ready and went home.

On Friday, I skipped classes, and spent the day out shopping for everything I would need. I returned home in time to prepare a nice dinner. Thomas got home around 6pm. He had played racket ball with a buddy of his. When he entered, I told him to grab a shower, dress and be at the dinning table in thirty minutes.

After a candlelit dinner, I told him to wait there and I would call him when I was ready. I went to his bedroom, lit some candles around the room, removed my clothing, lubed myself really good and replaced only my panty. I lay on the bed and called telling him that I was ready.

When he entered, he smiled at me, and slowly removed his clothing and joined me in the bed. He wanted to say something, but I shushed him and had him lie down. I lay beside him, him on his back, me beside and partially on him and I kissed him. We made out for awhile, then I slowly kissed my way down his body and proceeded to give him a slow blowjob.

I sucked on him just long enough so he was fully erect, which wasn’t very long. I stopped, removed my panty and straddled him. I rubbed my lower portions on his cock allowing him to slide between my ass cheeks. When I was ready I lined up his cock and slowly inserted him into me. I took my time to get adjusted to him. I slowly moved up and down taking a little more each time until he was fully inside me. I sat there on him moving side to side, forward and back enjoying his hot cock inside me.

He slipped out slightly as I leaned down so the two of us could kiss. After kissing for a bit I rose up looked into his eyes and told him this was the way it was supposed to feel. I told him I loved him being inside me. I moved off of him and lay beside him on my back and asked him to take over.

He put my legs over his shoulders entered me slowly and then pinned me down so that I was his. He fucked slowly for quite some time, stopping occasionally to tell me how good I felt on his cock.

I couldn’t speak as the gentle movements felt so erotic and wonderful. He pulled out and was slowly pushing in like he was trying to find something. He found it eventually; I let out a moan when he bumped my prostrate the first time. He continued until I was leaking cum in a steady stream. There was so much that it ran between my legs and was providing lubrication for him. The warm semen mixed with the lube was even silkier and felt wonderful. He continued until there was noting left in me.

He stopped, pulled out some changing the angle and slowly thrust all the way in. I told him I was feeling absolutely nothing but pleasure and to fuck me how he wanted. I told him, "I surrender to your pleasure."

He braced himself by placing his hands on my shoulders holding his self-up and started to pick up the pace. I placed my hands on his arms and looked into his eyes the whole time. He got up a pretty good pace and went at it for what seemed like hours. I felt him getting harder, and then he was banging into me as hard as he could until he slammed into me one last time and released. I felt at least eight pulses as he unloaded.

When he pulled out, he rolled me over to my stomach then did the unthinkable, at least to me at the time. He started to eat me out. He licked me clean of both lube and his own cum. While he was licking me, he reached under and between my legs and rubbed my flaccid penis until I had a dry orgasm. When my orgasm hit I screamed out “Oh, my God, Thomas, I love you."

He said he was going to go wash off and would be right back, I told him to lie down and I would clean him and proceeded to return the favor sucking the lube and cum from him.

We rested for an hour and just talked, while I fondled his cock. He started to get hard so I went down and gave him the full sensual blowjob that Tracy had given me.

Forty five minutes later he came into my mouth, and I held it in my mouth for a minute savoring his taste, then I swallowed. There wasn’t much this time and before I could turn around and lay by him he was out cold. I snuggled up to him and went to sleep.

I found out later that Trisha had spoken to him and had given him some lessons, seems they had messed around on Wednesdays at our apartment instead of studying or going out together. I was not jealous, as in the end she was helping him learn the care he needed to make love to me. She also put him in touch with the GLBT group on campus and they told him how he could please me that would blow my mind and his.

Finding out that he took the time to make sure I wouldn’t have pain during sex, made me fall deeper in love with him.

Back then, even though I told him often that I loved him; I could not fully come to terms with being gay. Neither one of us was comfortable to come out to our parents. At school though, we became an item.

Thomas graduated a year before me, but was able to secure employment in the area, so our relationship lasted until I graduated. Trisha met a guy she liked over the summer between our junior and senior years.

Wendy was devastated. I had never known what a girl goes through when she loses her love. I spent a lot of time giving her a shoulder to cry on, sometimes spending the night with her.

Once she was over Trisha, Wendy and I ended up on a girl’s night where we went out on the town as two girls. By that time I had acquired a wig, breast forms and would dress whenever the two of us were together. We even went further a few times, she teaching me how a woman makes love to another woman. She even gave me oral sex once swallowing even, but knew that it wasn’t for her.

After Wendy and I graduated we learned that Trisha was getting married in a few months, Wendy got a job out in California and left.

I was heart broken to see her leave, but we have stayed in touch all these years. She is still to this day my best friend. Someday I need to write about her and what her friendship has meant to me.

Wendy eventually met her life partner, and I was proud to be her maid of honor. No, I didn’t get to wear a dress, but I did wear a white tux with a pink shirt. The other bridesmaids wore pink gowns.

Her bachelorette party got kind of embarrassing, the male strippers I loved. The scavenger hunt got embarrassing pretty quick. Had to tell a random woman I desperately needed a tampon and for her to give me one. Had to run like hell for the dare of walking up to a guy and kiss him, on the lips. I did it, luck was on my side, he didn’t chase.

Tracy, the first girl I was ever with married after she graduated from college, no she didn’t go to our school. We ran into each other once when I was flying out of San Antonio . She had gotten an entry level job working for an airline.

I was checking in at the desk and was so surprised to see her. We chatted a bit but I had to get to my plane. When I got to the gate, she was standing there to check my ticket. She must have hitched a ride or something to beat me to the gate. I wanted so much to stay and talk with her.

I was seated in my coach seat near the back. About the time the door was being closed, a flight attendant told me to get my things and follow her. She sat me in a first class seat, and told me to call Tracy when I could, giving me her number.

After her divorce years later we got together again. Her husband had cheated on her. She remarried another cheater, we got together, and I came out to her. We were an item for a short time. She has never remarried and chooses to live the single life. I hope she finds a man that will love her the way she deserves. She is such a wonderful woman.

All through school Thomas never found out that I was a girl in disguise. I was afraid to tell him for risks of losing him. It was during my senior year that he told me that he loved me. That scared me even though I had been telling him the same all the time.

I felt that he liked/loved me because I was a guy. That he would hate me if I told him I was a female on the inside. I was also ready to explore my feminine side more.

After he told me he loved me, I was afraid he would come to terms with his being gay and would come out to his parents, forcing me to do the same. I just wasn’t ready for that step, and when I sent out resumes, I didn’t send any to my home state. When the only job offers showed up out of state, I took one out in Denver.

I used that as the excused that would break us up. Looking back on it and I tell myself I should have been completely honest with him. I also know that the way I treated him, that I don’t deserve to have him.

Leaving him was the hardest thing I had ever done. I eventually convinced myself that I wasn’t in love with him; I was in love with being his girl. That got me through a lot of years.

In the end, I found out that coming out to my mother, sister and the rest of my family was so much easier than leaving Thomas.

I gave up on my one and only True Love. I am so sorry.

I Love You, Thomas!

Then, now and until the day I die.

Epilog: This wasn’t the last time I ever saw Thomas nor was it the last time we made love. It was just many years later. And maybe I will cover it in a future story.