tagTranssexuals & CrossdressersTrans-itioning to a New World

Trans-itioning to a New World


I always thought I was a fairly typical guy. I'm a fireman, in a relationship with Melinda, my high school sweetheart. A short curvy blond with chin-length hair and brown eyes.

Went to the local community college. Had a chance to study abroad in my junior year, so after struggling through a Spanish immersion class, I spent a semester in Argentina. While in college, I joined the volunteer fire department on campus. I lived at the station with a few other guys, and in exchange for free room & board we would agree to be on-call to respond to fires and other emergencies on campus and in the town. Not a bad deal!

Unfortunately, things started to go downhill after graduation. I got hired by a fire department a few states away. That part was great! I was getting paid to fight fires and respond to medical emergencies. My girlfriend was still living back at home, enrolled at a college not to far from our hometown. We tried to see each other at least a few times a month. It got harder around exam time and when we had a rash of arson fires in my department's area. Our sex life had always been great. We could make love or just plain raw fuck. She was the adventurous type, so role-playing became part of our routine, along with a little bondage sometimes. However, I could tell that something was not right with Melinda. She became nervous around me when we'd see each other. She started to become distant when we'd have sex and wouldn't seem as enthusiastic to participate. I would have to be the one to initiate, which never happened before. The spice was quickly disappearing.

Melinda and I had a great friendship before we became lovers and future spouses. I would say our friendship was more important to us than anything. Overall, I just wanted her to be happy, and I could tell that she wasn't happy anymore. On my last trip back home, I took her to one of our favorite locations, a park by the big lake in town. We sat there on a picnic table, and the truth came out. And it was not what I expected.

Melinda confessed to me that she had met someone else and was starting to fall hard for that person. Part of me was shocked, but also it wasn't hard to believe, given her recent behavior. She confessed that she had met someone in one of her classes and there was a spark between them. They were part of the same study group, and that grew to seeing each other socially. Which led to a date. Which led to much more. She told me with tears in her eyes that she felt feelings for this person that she could not explain, that she had never felt with another person, not even with me. She was torn, confused, and even a little scared.

I was certainly hurt by all of this. Melinda and I had been close and so compatible. I knew that this was one of those "break-up" conversations, and there was nothing I could do. I resigned myself to the fact that our relationship was over. We sat for awhile, side by side, Melinda weeping and me not too far from that myself. The side of me that was best friends with Mel started to take over. I could tell she had more to say but didn't know how. I took her hands in mine and told her that as hurtful as this was, I didn't want to lose my best friend, that whatever happened between us wouldn't change that for me. She looked up at me with teary eyes and said she didn't know how to tell me. I told her to just say it. She paused and told me that the person she fell for was a woman. But she was not just an "ordinary" woman. She was transsexual, in the middle of transitioning from female to male.

That caught me off guard. Not that it couldn't be true, but that it was not what I expected her to say. Apparently, I must have had a really funny look on my face, because she looked at me with concern, and then couldn't help giggling. For some reason, it was infectious and I started laughing myself. I asked her what was so funny. She told me the expression on my face was priceless. Well, that seemed to break the ice. I don't know why, but for some reason, it took all the harshness of the moment away.

She told me about "Stephan" (formally known as "Stephanie") and how she/he was concerned and nervous as to what I would do when I found out. We walked back to her car and I told her I wanted to meet Stephan. She asked me if I was sure and I said yes. I told her I wanted to meet the one who captured my best friend's heart. That statement granted me a huge hug and a smooch.

The following weekend, I came out to visit Melinda and finally met Stephan. We got together at a local café and ironically, we hit it off right away. Stephan had an androgynous look about him, but the energy he gave off was very much male. We laughed and joked, sometimes at Melinda's expense, and I could tell that Melinda was ending up with someone special. What started out as just coffee between the three of us ended up with me being invited to the college's Lesbian/Gay/Bisexual/Transgendered club's potluck dinner. I have an uncle who's gay and a step-cousin who's a lesbian, so I was far from uncomfortable with this group. It was a nice meal with about 50 people from all walks of life and sexual/gender persuasions. Overall, I came away from the evening happy with the knowledge that Melinda was with someone who cared about her and would take good care of her, as well as a community of people who would also do the same.

The funny thing is, I came away with something else. At the dinner, I kept finding myself checking out some of the transsexuals. Several of the female-to-males, but mostly the male-to-females. Part of it was sheer curiosity, but there was something else there as well. I couldn't get over how sexy some of the MTFs were. One or two of them could have easily passed for women walking down the street. At first, it was an occasional memory that would come up. The thoughts started to come more frequently, and I realized that I was getting turned on even just thinking about some of those hot "women."

Eventually, I ended up going online and checking out some trans porn. Not all of the videos I saw were that great, but some of them turned me on, especially the ones with the passable trannies. I started reading transvestite/transsexual stories and articles on Literotica. More and more I found myself turned on by the thought of having sex with a MTF. Still, I was a little apprehensive about the idea. I had never fantasized about men or being with men. While I could see how women would find certain men attractive, I wasn't personally attracted to them myself. But I couldn't get the thought out of my head of what it sex would be like with a woman who was not quite a woman.

I started checking out the "t4m" Casual Encounter ads on Craigslist in my area. While most of the ads did nothing for me, I did find a few that turned me on. I kept coming back to one in particular. The person was submissive and was looking for someone to come over and have his way with her. She was open to anything, but was especially turned on by the idea of a "straight" or bicurious guy. And her picture, damn! Shoulder length straight dark hair with bangs in front, parted in the middle. Between the hormones and the implants, she was busting out of her bra. Her waist narrowed down and her hips flared out. One picture had her kneeling doggy-style on a bed in a thong and bra. I didn't think a guy's ass could be described as apple bottom or a bubble butt, but he had an ass many women would die for and certainly didn't look like a guy's butt. Another picture had her on her knees, looking coyly up at the camera, with cleavage that was definitely impressive. Her face was not entirely feminine, but was androgynous enough to be called pretty. Her cock was of average size and circumcised. For the first time, I could say that not only was I not repulsed by seeing a cock like this, but I was curious about it, what it would feel like, taste like.

I went to bed that night with thoughts of what it would be like to do her. I was hard as a rock and jerked off to the thought of her mouth around my cock. The next day I couldn't get her out of my mind. I created scenarios in my head of what I would do to her. I argued with myself about it. Should I go through with it? Would I be able to go through with it? While I knew that the idea of her with a woman's body and a cock was what was turning me on, I wasn't sure if I was ready to interact with someone else's penis & balls. I decided that if I was going to take the plunge, I would have to make baby steps here.

I sat down and wrote out an email to the wo/man in the ad.

"I saw your ad on Craigslist and I think I fit the bill of what you're looking for. When I read your ad, this is what came to mind. I will come over to your apartment. You will have already cleaned yourself out with an enema and lubricated your ass before I arrive. You will be waiting for me at the door, on your knees like in the picture in the ad. You will wear that outfit for me, and you will be blindfolded. I will come in and we will not speak a word to each other. I will stand in front of you, unzip my pants, and take out my cock. You suck me, getting me hard in your mouth. I will take your head in my hands and fuck your mouth, thrusting deeper and deeper. I will stop before I come. I will take you into your bedroom and lay you face down on the bed. I will straddle your ass and you will pull your cheeks apart with your hands. I will slowly slide my hard cock into you and start thrusting in and out. I will grind you, pinning your hips to the bed and fuck you harder and harder until I come, filling your ass with my seed. You will remain on the bed, face down, blindfolded, and I will get up and leave, without a word being spoken between us. If you satisfy me, I will consider a repeat performance, perhaps introducing other elements to our game."

I read over my message. I took a deep breath and hit send. I thought about what I had done. Did I do the right thing? What if s/he wrote back? Would I have the guts to carry through? Would I even really want to carry through on it? Well, even if he did respond, I could just ignore it and pretend I never sent the email.

About an hour later, an alert popped up that I had a new message waiting. I paused for a moment, not sure if I should open it. I did. It was from her.

"I have had many email replies to my ad, but none of them turned me on like yours did. I am home now. Let me know when you will be coming so I will be ready for you."

Holy shit. I re-read the message. I was slightly shaking, but getting hard at the same time. This was really happening! I thought for a moment, and decided that it was now or never. At some point, I would have to confront my desires, and now was as good a time as ever. Plus, I was in control. I could stop or call it off at any time. The fact that I was getting hard just thinking about this scenario convinced me that it was supposed to happen. I fired off an email, telling her to send me the address and I would be there in an hour.

A few minutes later, another email shows up with an address to her studio apartment about 30 mins from me, telling me that she will be waiting, blindfolded on her knees to service me.

I got goose bumps. I jumped in the shower, then left, dressed in non-descript clothes with a hooded sweatshirt. I figured that I could always cover my head to help keep this anonymous. I arrived at the address, a nice looking apartment building. I got out of the car, put up the hood, and walked up to the front door, nervous as all hell. I rang the bell of the apartment and a few seconds later the door buzzed and unlocked. I walked in and took the elevator to her floor. I got out and stopped in front of the apartment door. She had taped a piece of paper to the front door. "Come inside, I'm waiting for you." I took a deep breath, opened the door, then stepped inside and closed it.

The studio apartment was clean and neatly, but tastefully furnished. No closets but lots of coat racks, and I could see the empty bathroom through the open door. But most of all, I could see her. Or him. Kneeling on a rug in the entryway. She looked just like her picture, only blindfolded. No, she looked better than her picture. Her nipples were visible through the sheer bra which held a pair of 38D breasts. I could tell from the front of her thong that she had a medium sized penis, though it was contained by the fabric. I was happy that I still found her attractive. Stepping in front of her, I unzipped my pants to the floor and pulled out my cock. She heard the sound of the zipper and a small smile appeared on her lips and her breathing quickened. I stepped closer and felt her hands touch my legs. She ran her hands up the front of my knees and thighs. A soft hand with manicured nails took my dick into it and she leaned forward, opening her mouth, and I watched in amazement as it enveloped me into a warm wet place.

I'm not sure what I expected, but it's true when they tell you a mouth is a mouth. She definitely knew what she was doing. She ran her tongue on the underside and around the head, providing suction as she pulled her head back. I closed my eyes and groaned as I felt myself quickly getting hard. She slid her mouth back down my cock to the base, then slowly pulled out again. It only took a few more times of that before I was rock hard. She plunged herself down to the base and I felt my head against the back of her throat as my penis throbbed. She moaned, although the pitch and timbre was not that of a man. She started bobbing her head up and down, sliding almost all the way out, stroking me with her palm and fingers in rhythm to her movements. The sensation was heavenly. Melinda gave great head, probably the best I had ever had, but this came pretty damn close to rivaling that. My mind spun. I was getting a blow job from a guy. I know she wasn't really a guy, but she had a penis all the same. And I wasn't repulsed by it. Probably because it felt so good and from above he looked very much like a woman.

My hips started involuntarily moving and I took his head in my mouth, my fingers wrapping around his soft hair. I started thrusting in and out and she rested her hands on her knees. As I face fucked her, she made little grunting sounds, especially when my cock touched the back of her throat. I was incredibly turned on. She leaned into my thrusts, trying to take me deeper in. This caused her back to arch and ass to thrust out, bobbing along with her head on my shaft. The sight of the string of her thong disappearing between two virtually perfect ass cheeks got me even more heated. I forced her head down all the way, burying her nose into my pelvis. She gagged a little for a second and then almost squealed when I pulled back off of her. My cock slid out of her mouth and she gasped, panting. I pressed the head against her lips and she opened up to take me in again. This time I could feel her try to press forward to take me all the way into her throat again. I obliged, fucking her harder and faster. I could hear her moaning in time with my thrusts. I throbbed and panted, feeling myself get close.

I slid out of her mouth and she whined, missing the feeling of being taken orally. I took her by the arm and pulled her up and spun her around towards the bed, making her gasp. I pulled her over to it and pushed her down onto her stomach. That ass was in front of me, and I couldn't believe it belonged to a guy. She had laid out some condoms and lube on a table next to the bed. I grabbed the lube and condoms and got onto the bed, straddling her knees. As I put a condom on and slathered lube all over it, she reached back with her hands and slide the string of the thong down and spread her cheeks, exposing her asshole glistening with lubricant. In this position, with her legs pinned tightly together, I couldn't see her cock or balls. It was almost, for all purposes, a woman's ass in front of me. That's what she wanted me to believe. I knew it wasn't the truth, but it didn't matter. The ass in front of me was beautiful.

I leaned forward, guided my cock to the rosebud of her ass, and pressed against it. I heard her sigh as I watched the sphincter relax and head started to disappear inside. I'm not sure what I expected. I had had anal sex with women before and it was always an amazing experience. This time was no different. As the shaft slid further and further into the soft, warm tunnel, I felt pleasure flow through me. She let go of her cheeks and gripped the headboard in front of her as I leaned over her on my hands. I pressed down with my hips and slid the rest of the way into her ass. Her sighs turned to groans as I hit bottom, my thighs nestled against the cheeks of her ass.

In all honesty, her body did not feel much different from that of a woman. A little more firm, slightly more solid, but otherwise very similar. I laid on her back and began grinding into her, thrusting in and out. Gripping her shoulders, I saw her mouth open, gasping, panting. I was completely turned on in ways that I had never experienced. I pounded her, fucking her harder and harder. I heard her whisper "yes...yes...yes...yes!" Gripping her shoulders, my assault on her ass increased, feeling waves of pleasure pulsate through me. I knew I was hooked on this. My hips slammed into her so hard the bed rocked back and forth. I felt that familiar tingling and knew I wasn't going to last much longer. I pinned her body to the bed and groaned as I exploded inside her, convulsing and throbbing, filling the condom with cum. She felt me spasming and squealed.

My orgasm subsided and we both lay there panting. I noticed a smile on her face, and I have to admit there was one on mine as well. After several moments, I slid out of her. She gasped and moaned as her ass became empty. Somehow, I gathered the strength to get to my feet. I peeled the condom off my softening cock and tossed it in the garbage. She laid on the bed, breathing heavily, her ass moving slightly as if I was still sliding in and out of her. I dressed and walked to the door. She remained face down on the bed, honoring our arrangement to lay there, silent. I walked out of the door, almost off-balance. As I walked to my car, I knew. This would not be my first and only time with a trans person. I had a feeling I knew who I would be emailing as soon as I got home....

[Will our gentleman continue his journey into new experiences? We shall see....]

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