My First Time(s)

Hi, I am Leigh, a Crossdresser (CD), Caucasian, 68″ tall, 30″ inseam, 28″ waist, 34″ hips, green eyes, and shoulder length hair. I have always had soft facial features, women’s size 8 or 10 depending on the brand.

I wanted to write about my first time, something I think everyone reading this has experienced. I want to include what I was thinking and what events lead up to this point in my life so I am writing this as a confessional story to you the reader. Some may read this as entertainment others may read this and have had similar experiences and maybe others will read it and understand they are not alone…enjoy:

On my 19th birthday, my girlfriend gave me two pairs of baby blue men’s spandex bikini underwear. These were the closest thing to women’s panties I had ever worn and in the following weeks I bought several pairs of exotic male underwear to try, some were thongs and others so high cut in the hip that they were barely recognizable as men’s underwear. This was just the beginning for me.

I would not admit to it but I had a curiosity about sleeping with another man, but I did not know how or where to meet someone that could help me satisfy my curiosity, then I met Dave…

It was during collage and I was working the early morning shift at a hotel restaurant as a server, the dress code was black pants white dress shirt and black bow tie. The early morning shift consisted of myself and a Renee who cooked breakfast, Laura came in later just as we opened. Dave, the third shift maintenance/cleaning person stayed until the manager arrived to open the restaurant.

Dave was about 15 years older than I was and carried himself in a masculine manner and was always pleasant towards me. From what my coworkers told me Dave was gay and in the back of my mind I often fantasized Dave would make an advance towards me and I could satisfy my curiosity of being intimate with a guy.

The restaurant hosted many local civic organizations meetings in the mornings requiring me to set up their room for them. This morning was the Optimist International club. I came in and started making coffee then headed to the back to start setting it up for the meeting. I walked in, and found all the tables and chairs arranged according to the “club flow chart”. I thanked Dave for setting things up for me; he shrugged it off saying: “I had to move the tables to vacuum the floor last night and it wasn’t too much effort to make my “sweetie happy”. I thought Sweetie was an odd name to call me but Dave was a little odd in his own right.

The next morning I was loading dinner salads in the cooler on the server line. This cooler had a glass lid you opened and had to lean in to load it or pull something out of it. While I bent over the cooler, Dave came up behind me, pressed his hips against my ass, and said something to the effect of being so close to heaven as his hands slid up and down the sides of my hips. Dave didn’t linger he was gone before I pulled myself out of the cooler but when I turned around Laura was standing there frozen in mid-step looking at me with her mouth open in shock. I dismissed what she saw with a disparaging comment about Dave and his gay antics.

Over the next several weeks, I would be reaching or bending for something and Dave would come from nowhere and touch me or complement me on how nice I looked that morning always referred to me in the feminim with sweetie, missy, or his sexy girl; but never with my real name. Soon Renee and Laura would give me a knowing look, excessively often as if they knew something I did not or worse they knew I wanted to be with a guy. Over the next few weeks, Dave continued his sexual advances towards me and often commented on my choice of underwear for the day, claiming he could see the outline through my dress pants. Secretly I appreciated the attention and wanted to experience man on man sex but I was just too shy to come out and ask for it. Granted Dave would not have been my first choice but he seemed my only choice.

I decided to come in on third shift when I knew yenibosna escort Dave would be working alone, I just wanted to talk with him and ask that he be a little more subtle and explain to him what was going on in my head. I arrived at work 2 hours early; I had to ring the delivery doorbell three times before Dave opened the back door and I almost chickened out. At first, he looked annoyed then realized I had come in extra early and welcomed me inside. I had mental rehearsed everything in my head, what I was going to say and what rules I needed to lay down between Dave and I. Then, I chickened out, I lied and told him I knew the party in the back room would take extra time to set up so I came in early and I had to fill a large urn of coffee, and do my normal work. I ignored Dave’s advances and hurried to the back dining room, I needed to think, and regain my nerve. When I walked in the room everything was set up and ready to go. Dave walked in, wrapped his arms around me and asked if he did a good job.

Dave tried to kiss me but I halfheartedly tried to push away from him; but with my arms pinned between our chests, all I could do is turn my head allowing him to kiss my cheek. Dave undeterred continued open mouth kissing my neck. I rolled my head back giving Dave full access to my neck; I was enjoying this as much as he was. Dave turned us so my back was against the wall and his body pressed firmly against mine he was able to pull my chin around for the kiss I denied him earlier. I knew exactly what I was doing when I allowed his tongue past my lips. I shocked him when I said wait and pushed myself away from him.

I knew I wanted to suck cock and at that moment, I was going to suck Dave’s cock, before I chickened out.

Playing on his fear of the manager’s morning inspections, I asked Dave if he changed the burned out bulb in the restroom, with a shocked look he went straight to the restroom attached to the banquet room. I was right behind him and locked the door behind us. Dave was surprised when the light worked but not as surprised when I dropped to my knees in front of him.

There I was on my knees, sitting on my heels and Dave just staring at me. I ordered him to drop his pants. Everything moved in slow motion, the undoing of his belt, then the button on his jeans and every click his zipper made, his cock springing free of his underwear to point directly towards my mouth. Soon, I was looking down the barrel of his cock and my lips were inches away from sucking their first cock. I watched his cock move closer to my face, when it touched my lips I closed my eyes and let Dave slide his manhood past my lips.

Nervously I allowed Dave to hold my head with one hand as he began sliding his cock back and forth across my lips gently feeling his cock slide across my tongue, and then rub the roof of my mouth in the back, near my throat, then withdraw to repeat the rhythmic back and forth motion. I forced myself to open my eyes and watch as his cock slipped back and forth past my lips and into the back of my mouth. In my peripheral vision I saw caught our reflection in the mirror and became very turned on at the sight of my lips holding a cock.

Dave was gentle at first, but quickly began fucking my mouth with both hands holding my head. I watched as his hips thrust towards my mouth and I watched at the end of each thrust the sides of his buttocks flex as they gave that little extra push, ensuring his cock was all the way in before pulling it back for the next thrust. My mouth became his plaything for almost twenty minutes before his thrusts became quicker and more determined and forceful. A light bulb went off in my head, from experience, I understood the significance of this and I knew Dave was getting close and I needed to make a decision to swallow or not to swallow. After a few moments Dave made the decision for me, he pushed hard until his balls were against my chin and his grip on my head was inescapable and he was motionless. Dave’s cock shot the first kayaşehir escort load on the inside of my cheek then the next few loads flew deep into my throat. He did not relax his grip my head, he held me there as I swallowed every drop of his seed. I held him in my mouth until his breathing started to return to normal and his cock began to soften then I let it slip from my mouth. I told Dave to pull himself back together as I left to start my shift.

I kept to myself for most of my shift thinking about what happened. Even though I was the one who lured Dave into the men’s room, I felt submissive and used; a man took advantage of my mouth and used it for his enjoyment without any respect to my needs, and I loved every second of it!

The next day Dave made a pass at me in the walk-in cooler and I stopped it right away. I tried to explain what happened and I did not mean to hurt him but I was in an experimental phase of my life. I thought he understood so I went about my business as if nothing happened, but as the days went by it was obvious that Dave had said something and everyone knew what had transpired behind closed doors. The women I worked with were ok with the idea I liked guys but not the idea of my first time being with Dave. The men I worked with hated me, called me a cocksucker and made it known I needed to stay away from them. My first shift coworker Laura pulled me aside and told me if I needed to talk, she was always there. I made sure she knew I appreciated that.

Things got perpetually worse at work for me; my male coworkers threatened me every day. The girls were cool with everything except who I did it with and eventually tried to set me up with their gay friends; I could not stay here any longer and I needed to find a new place to work.

Still a virgin, I moved away that summer and eventually I met Peter. Again, I am with an older man, Peter was easily in his 40’s and had been in a relationship with another man for at least 10 years when I came along.

I know what you are thinking, shame on me for getting involved with a man in a relationship, but I thought it was safe that he would not fall in love with me. I wanted to experiment not jump in headfirst.

Pete and I met a few times in the mall parking lot just to chat. I told him my story and what I was looking for and any questions I had Pete always answered them in a way that did not make me feel stupid. After about the fifth meeting I was beginning to trust him and I invited him to my house. Up until now, Pete never made an advance towards me, never made me feel nervous, or worried things would move too fast.

Pete arrived at my house and was a perfect gentleman, he even gave me a gift, and it was green frosted glass paperweight form the 1930’s. Pete was into antiques and he was right I loved the paperweight.

We chatted for about an hour before Pete asked if I had ever watched gay porn before. Truth be told I had never been exposed to it. Pete excused himself to his van and returned with a gym bag, from it he produced several porn titles one of them was a transgender movie, and that is the one I selected.

I moved to sit next to Pete as the movie started, not sure, how far into the movie, we were when Pete slipped his arm around my shoulder but I think it was half way through the move when he asked if I enjoyed kissing.

I told him I wanted to experience it all and before I knew it, he moved in and it was lips against lips. It was gentle kiss, his eyes were searching my face for a reaction, and he kissed me again. Feeling his beard and moustache against my face made me feel odd, it was different, hard for me to describe. His facial hair made him seem more masculine and made me feel more submissive because of my smooth face.

Pete wanted more and when I felt his tongue, I opened my lips and allowed him to French kiss me. His tongue was freely exploring my mouth, a man’s tongue; I was lost in that thought.

I jumped when his fingers found my nipple bomonti escort and when he started playing with it between his fingers all I could do was throw my head back. The feeling was incredible, uncomfortable, and strange all at once. Pete trailed his kissing down my exposed neck as he continued to play with first one then my other nipple, and then his mouth replaced his fingers. His tongue on my nipple, his facial hair, and his lips sucking made my toes curl and my hand to move to the back of his head as I explained how incredible that felt. I asked him if he was ready to move this party to the bedroom.

As we entered the bedroom I explained this would be my first time and regardless of what I said, he was not to let me chicken out even if he needed to hold me down this was something I wanted. As he undressed, I dropped to my knees in front of him jokingly holding my mouth open for his cock.

I had no idea how big or how small Pete was until his cock slipped free of this boxers and smacked me in the cheek. His cock was 6″-7″ long but he had a huge purple head, I mean it was more than double the thickness of his shaft. I began sucking his cock wondering if this was going to fit inside me without damaging anything.

I did my best to suck on that giant purple head before allowing more of his cock into my mouth. I bobbed my head on his cock while thinking about being fucked for the first time and before I knew it Pete came, I swallowed without thinking about it, it just happened. I thought my chance of being screwed was not going to happen but Pete did not miss a beat, he asked me to lay on my stomach on the bed. I did as he asked.

Pete laid on his side next to me as he applied lube to my ass. This was a new form of foreplay as his hands moved up and down my ass until finally he slipped a finger inside of me. I remember thinking how ironic it was that I just got goosed. Pete was enjoying my body as he continued to lube my ass, telling me what a great ass I had and how lucky he was to be with me, until he could slip a second finger into me. It hurt but he was gentle, that is until he tried to slip a third finger in.

I turned to look when I heard the foil wrapper noise; Pete’s cock was hard as a rock as he slipped a condom over that giant purple head of his. Pete told me to breathe in through my nose and out through my mouth as he straddled my ass. I could feel his cock slid between my ass cheeks then it slid up and down looking for its target. I was going to be fucked by a man and all I could do was let him, then his cock found my opening and started pushing itself into me. I said it was not going to fit; it was too big, Pete told me it was going to be ok, I thought maybe I needed more lube.

It hurt but he continued to push until the head of his cock pushed into me. I literally saw stars. Pete stopped with just the first inch of his cock inside me telling me it was going to be ok and that I needed to relax. He was right, my body adjusted and he pushed more of himself into me until I felt his hips firmly against my ass. Pete let out a low fuck your tight comment then he started to pull back. Then he started to push back into me soon Pete was in a rhythm and it went from uncomfortable to enjoyable.

There I lay, with a man on top of me with his cock firmly inside my body, I did it; I was being fucked, something I had thought about for a long time. Ever since I saw my first Play Girl and wondered what it would be like to have the hairy guy in the centerfold fucking me.

Occasionally I would feel the cock inside of me poke at something, a quick sharp pain making me wince and moan that encourage Pete to fuck me more forcefully. I was enjoying myself, I looked over my shoulder and told Pete his cock felt amazing. Then after a down thrust he pushed up towards my shoulders with his cock, he was deep yet trying to push farther into me with hard-determined thrusts. His thrusts got quicker and I had to push back on the headboard to keep from hitting my head. I knew he came, he thrusted into me a couple more times but it was over.

Pete rolled over onto his back; I laid there feeling completely empty so I moved to lay my head on his chest. I thanked him for taking my virginity. He laughed, but I was serious. I placed his hand on my ass and told him this is yours whenever you need a quick piece of ass. Soon we drifted off to sleep.