It had been six years since my experience with Chris in the move theater. Much to my disappointment, we never did share another passionate session together. While I knew he enjoyed it, he got a girlfriend shortly after, and we didn’t take much. I moved away to college and got a girlfriend myself. I occasionally thought back on, and masturbated to the day in the theater with Chris, but that part of me slowly faded away. Especially the longer I stayed with my girlfriend. However, not to long ago, she left me. Obviously I was devastated at first, she was my first love and we had spent years together. I didn’t date afterwards, instead choosing to focus on both my schoolwork and job. By the time I had graduated, I hadn’t been laid in over a year, and I was getting hornier each day. Eventually, I started to focus more and more on that day with Chris. It made me crave dressing up, taking a cock and making it cum harder than it ever had.
For awhile, I only thought about it, allowing fantasies and masturbation to satisfy my urges. But as anyone with a fetish knows, eventually you have to act. I didn’t know how I wanted to start though, and unlike the past, there wasn’t a certain guy I wanted. That all changed one night when I went to a nearby pizza restaurant and saw him. I didn’t know his name, but he was a tall, well built, tanned god. He was probably 6’3”, 215 lbs, mainly muscle. However, his looks weren’t what I was attracted to at first. I could see a large bulge in the front of his pants, he was clearly hung. He grabbed some pizza and left, he was a delivery boy.
I went back home and pleased myself all night thinking about it. I knew I wanted him, but I had absolutely no idea how to get to him. I was convinced the only way to get to him was to trick him into wanting me.
I had no clothes of my own to dress up in, so I traveled into town and found a lingerie shop. I found a very hopeful lady and told her my girlfriends fantasy was for me to cross-dress and I wanted to surprise her. I tried on countless things, trying to find the perfect combination. I had many things I needed to hide, so not everything was possible. I eventually settled on a tight black skirt, with black leggings. As badly as I wanted nice smooth legs, that would cause more questions than I wanted to answer in my other life. She picked out a nice pair of heels for me that pumped up my legs and ass. Every time I passed a mirror, I couldn’t help but check it out, perfectly plump, even I wanted to squeeze it. For the top, we settled on a white blouse. I was hesitant at first, since it was kind of low cut, and I had nothing to fill it out. She calmed my nerves though by getting a push up bra and showing me a trick to pump up my “breasts” with tape. While they certainly weren’t huge, I couldn’t deny it created a nice mirage of cleavage, which was all I needed. As for the wig, we settled on long dark brown hair to match my eyes, it flowed just below my shoulder blades. I’ve always had an androgynous face, which made me at least passable if I applied makeup. We got a scarf for my Adams apple and after 30 minutes, she made up my face into a fairly attractive woman. She convinced me that it would be all about my eyes, as they’re extremely dark and seductive. She applied a complimentary amount of eye shadow and mascara, hoping that my eyes would be engaging enough to keep focus on them, and not look at any other details.
I walked out of the store feeling like a whole new women. I was confident, but more than anything, I was hornier than I ever had been. As I was putting my keys in my car, I noticed a man checking my ass out. Normally flattering enough, it was even more exciting when I checked out his very attractive girlfriend right beside him. Even if for just a second, I was hot enough for him to stray his eyes away.
I drove by the pizza place and saw that he was working, my cock got extremely hard as I contemplated how I would try to seduce him. I drove home and calmed myself, my body shaking in excitement. I called the place up, and using my most feminine voice, ordered food for delivery. The voice at the end of the phone seemed convinced enough, as he called me ma’am throughout the exchange. I spent the next twenty minutes glued to my front door, my cock throbbing, almost to the point of pain. I needed to suck that mysterious man off. My heart was beating faster than ever when the door knocked, my heart nearly stopped. I was frozen for 30 seconds before the door started knocking again. I stood up and started walking towards the front door. Forgetting that I was in heels, and my legs feeling like jelly, I tripped on the way over and stumbled.
“Everything all right in there?” A deep voiced asked from the other side of the door.
“One second.” I called out, nearly speaking in my normal voice.
I picked myself up, adjusted my bra and skirt and took the last few steps to the door. I opened it, and couldn’t help but squeak in disappointment. The delivery man wasn’t who I was hoping for at all. Rather, in my doorway stood a medium height, overweight middle aged man. Around 45, his gut hung over his belt, his shirt was sloppily tucked in, his hair was partly gray and poorly kept. His face, round and greasy, covered in a poorly trimmed beard. My heart sank, as well as my cock.
“13.50.” He said, his voice shaky.
“Oh, yes.” Disappointment clear in my voice. I walked to the table and while grabbing the money, the change slipped out of my hands to the floor. I bent to the ground to get it, and when I looked back, I saw his eyes sizing up my ass, his jaw partly dropped. Although he wasn’t my mystery man, at least he still made me feel sexy and desired.
He quickly shifted his eyes, pretending to look around my house instead. I got up and walked towards him. I could see movement around his belt, and couldn’t help but smile as I saw a tent rising in his jeans. Surprisingly enough, that movement began to stir movement in mine as well. I was getting hard. I decided right then that I didn’t care who it belonged to, I just needed cock.
I gave him the money and watched him as he counted out the exact change. I could see the disappointment in his face when he realized there was no tip. I took the pizza and he started to walk away when I seductively whispered, “I’m sorry there’s no tip, I’d gladly take yours to show my thanks.”
I wasn’t sure he caught my drift as instead of getting excited he sat there dumbfounded. I hastily grabbed his arm and pulled him inside.
“What…” Was all he managed to stammer as I pulled him to the couch and sat him down.
“Just enjoy this.” I whispered in his ear before getting on my knees in front of him. Before taking off his jeans, I rubbed my hand against his cock, trying to get a feel for how big he was. Somewhat disappointingly, he seemed to be of average length. No matter, when I looked up at him and saw the look of pure joy on his face, the size of the cock didn’t matter. I wanted to make this man’s year. I undid his belt and using both hands removed his jeans.
I grabbed the base of his cock and pulled it towards my mouth. Before it made contact with my lips, I gently rubbed it against each of my cheeks. It was completely hard, but even better, it was hot. My checks got warm as I rubbed him against my face, letting him know that I was all his. Teasing both of us enough, I finally let my lips touch the very tip. I kissed it, and waiting the last 6 years to feel another cock in my mouth finally overcame me. I was in a frenzy, I went straight for the deep throat and took all 5 inches. I was out of practice, so I had to fight off my gag reflex, but it was worth it. As my lips wrapped around the very base of his shaft, I could hear him groan in delight. I then very slowly went back up his shaft, occasionally putting pressure from my lips on him. Reaching the top, I begin to kiss the sides of his dick, frequently sliding my tongue around it, coating it in my saliva. Each time he moaned, it only made me try harder. I went back to deepthroating him, speeding up every time I went down. I could feel him pulsating in my mouth, and I knew that while I wanted to do this all night, he was going to cum soon.
“This feels…so…fucking good.” He struggled to speak, but I didn’t need him to say anything.
I very seductively looked up into his eyes, he could barely keep them open. I was swirling my tongue around the head of his cock, and with each passing circle, he would look up at the ceiling. I brought my hand up and began pumping his shaft. I very briefly took my mouth of him, but only to whisper, “Give it to me.” With that, I began to suck his cock as passionately as possible. My tongue playing with his cock, my hand pumping away at his shaft. The next moment, I felt his large, stubby hand on the back of my head as he forced me down. The tip of his cock pressed against the back of my throat. And then, 6 long, powerful bursts of his hot cum filled my mouth and throat. Not knowing when I could do this again, I kept my mouth around him as long as I possibly could. Eventually, he got to sensitive and pulled me off. His cum still in my mouth, I played with it with my tongue. Enjoying the hot, salty taste. Eventually, while looking him dead in the eyes, I swallowed it all. I stood up, grabbed his hand and placed it on my ass. To my delight, he squeezed.
“This was the best day ever, and I want to stay for that ass, but I’m late for work.” He said excitedly.
“Don’t worry, you gave me what I needed.” I couldn’t help but wink as I finished. He pulled up his pants and left. As I closed the door, I couldn’t believe I got so horny for an old, overweight man. But I was as hard as I had ever been. I went to my room and thought of each second his cock was in my mouth. I had the most amazing orgasm of my life, alone. I couldn’t help but think if I would do this again, and especially how I could trick someone into fucking my ass without figuring me out…