The next night after talking to Nick, I got up, did my stretching, ate breakfast, and wondered when or if Joey would call me. I didn't wait that long as that night, I got the phone call. I didn't recognize the incoming number and hoped it was Joey. It was. He introduced himself as Joey and told me Nick said he should give me a call. He asked me if I wanted to hang out soon and get to know each other, maybe get something to eat and go watch a movie. I of course said yes and said we could meet that night if he wanted; my horniness was apparently winning out over my shyness. He agreed and said he would pick me up in a couple hours. I called Nick right away and told him Joey had already called. I picked out the outfit I would wear that night if he wanted me to dress up and set it aside. Even though I am naturally pretty smooth, I shaved everything, my pubic area I always kept shaved. I took a shower and gave myself an enema. I wanted everything to be perfect. I put the condoms in my drawer by my bed next to the lube and I was all set.
Joey came by about 8:30 and picked me up so we could get something to eat. I of course stayed in my guy clothes as we went out. He told me I looked good and I had a good body. Joey looked pretty good himself. He was 6'3", good shape, had a goatee, and I was immediately attracted to him. We went to the Olive Garden and just talked and got to know each other a little. I found out he was going to graduate in the spring, was going into business, and liked hiking and camping. I told him I had never been before and he said maybe we could go sometime. When the check came I tried to pay my share but he said not to worry about it that he would take care of it.
We left the restaurant and Joey said "Why don't we skip the movie. Nick said you had something to show me anyway." I agreed and we headed back to my apartment.
"So you've really never been with a guy before?" He asked as he drove.
"Not yet." I replied.
"Well if you just want to dress up and fool around a little that's ok with me." He informed me. "If you're nervous we don't have to do everything." I just nodded in reply.
When we got inside my apartment I got him something to drink. "Why don't you go get dressed up for me? I've been looking forward to seeing your hot body in a skirt ever since I saw you." He directed.
I immediately got the outfit I picked out and headed to the bathroom. I was sooo excited! I was actually going to get to play with a hot guy and his cock! I started putting on my outfit. It was a short black skirt, with thigh highs, a short black top that showed off my flat tummy and my back, a black strapless bra that I stuffed a little and a black thong that said "flirt" over the butt. I then put on my blonde wig that I had brushed that morning and began applying some makeup. I really wished I was better at makeup since I never had anyone to show me how. I was doing ok on it though as I applied the lipstick and eye shadow.
"Are you almost ready?" Joey yelled from the living room.
"Almost." I replied in my best feminine voice. I wanted to make sure I looked great before I walked out there. I flipped up my skirt, adjusted my thong perfectly and admired how it framed my ass. I then made sure my "boobs" were in place, took a deep breath, and walked out.
Joey stared at me for a few seconds as I anxiously awaited his response. "Wow, you look great! I wasn't expecting the whole makeup and everything too."
"Thanks." I said. "You look great too. I was a little shy to tell you earlier."
Joey nodded and said, "Turn around for me. I want to see what you look like from behind." I obliged and flipped my skirt up for him so he could see my thong. "Hot! Come over here sweetie."
I sat next to him on the couch and he immediately started kissing me. It was my first French kiss ever, and I loved it! He had his big hand on my bare tummy and I felt like a woman. After a few minutes he commanded me to sit on his lap and straddle him. I obeyed and his hands immediately went up my short skirt to grab my ass. With his firm grasp I could feel he was stronger than me and it made me want him more. He started playing with my thong and I could feel his erection growing underneath me. He then put one of his hands in front of my mouth and told me he wanted to see me suck on it and to get it nice and wet. I obliged and pretended it was his cock as I licked and sucked his big fingers till they were wet. He then moved his hand back down to my ass and moved my thong to the side with one side as I felt a finger on his other hand against my ass. "Oooohhhh" I moaned as he gently started to slide it in. I could still feel a little friction as he probed my ass but I absolutely loved it. We continued to kiss as he fingered my ass and I moved a hand down to his cock. I unzipped his pants and started rubbing his cock through his boxers. He moaned and grinded his hips a little.
"I want you on your knees and my cock in your mouth." He whispered in my ear. I was so happy to hear this I immediately dropped to my knees, only a little sad to lose his finger out of my ass. I pulled his pants off and then his boxers. I was greeted with his cock springing up. I took a hold of it and examined it for a second. It was a very nice looking cock. I'd seen some before online and stuff but I had never seen one in person except my own. It was definitely bigger than mine both in thickness and length. Judging it against my six inches, I guessed it at a little over seven, probably seven and a half. All I was for sure of was that I wanted it in my mouth. Remembering the advice I got from Nick the night before, I started at the bottom of the base and licked up. His moan let me know he liked it. I licked it a couple more times and then I started to put it in my mouth. I slowly slid my mouth down it, trying to see how much I could get in. About half way down his hips moved up and his cock went further down my throat and I gagged a little. "Sorry sweetie. Take as much in as you can." He told me. Despite that, I loved sucking his cock. I really started getting into it, bobbing my head up and down faster and faster. He had his hand on the back of my head and I loved the feeling of him being in control as I sucked his cock. After what seemed like only a minute of fast sucking by me he said "Hold on baby, I'm going to shoot." He had his hand on the back of my head and I hadn't planned exactly where I wanted him to cum but I didn't want to stop sucking. Seconds later he came and spurted shot after shot in my mouth. A little scared to swallow, I let it drip out of my mouth and back down his cock. After he was done shooting, I looked at his cock and his cum oozing around it. I could taste the cum on my lips and was a little sorry I hadn't swallowed.
"That was great!" He exclaimed. "Are you lying when you said this was your first time?"
"No, honest. That's the first time I've done anything with a guy."
"Well, you're a natural." He said which is exactly what I loved to hear. "I left a little white stuff on your face though." He laughed. "Go clean it off, have a glass of water and come back here though." I obeyed and then sat next to him on the couch.
I was still horny though and asked "Do you still want to fuck me tonight?"
"Of course." he replied. "I just need a couple minutes." As he put his arm around me to feel my bare tummy between my skirt and top. We turned on the T.V. and luckily, since it was almost midnight, there was some soft core porn on HBO. We watched that for a few minutes and saw a woman doing a little striptease for her man. "Can you dance that good?" Joey asked with a smile.
"Maybe." I said coyly and started to dance a little for him. I flipped up my skirt a lot, making sure he got a good look at my ass, and played with my thong like I was going to pull it down. Then I got on his lap with my back towards him and started grinding against him. I felt his cock growing a little so I reversed myself and straddled him and began to kiss him and play with his cock.
"OK, I'm ready." He said and jumped up. He took me by the hand and led me to my bedroom. "Lie on the bed on your back baby." He commanded. I obeyed and he laid on top of me with my legs wrapped around him and kissing me deeply. I could feel his cock pressing against the cloth of my thong and I wanted him badly. "Where's your lube?" He asked and I reached for the drawer as we continued to kiss and handed him the lube. He pulled my panties down and off my legs and I loved the feeling of air up my skirt and the anticipation of my first fucking.
He opened the lube. "Use a lot." I informed him as he nodded in understandment.
"Move your knees up as close to your face as you can" He ordered, then added "Wow, you're pretty flexible." As I tucked my knees to my chin.
"Thanks." Was all I could manage as I grinned.
I squirmed a little as I felt the cool lube on his fingers inside me. He really lubed me up good and I wondered how good his cock must feel if his fingers felt this good.
He then started kissing me and whispered in my ear "I don't have a condom, but I'm clean sweetie."
"Nice try." I thought but told him,"Don't worry, I bought condoms. They're in my top drawer."
He sighed a little and grabbed one and put it on. I stared fascinated as I watched him roll it over his cock. He then squirted more lube on it, told me to put my legs up, and laid on top with his cock pressing against my hole. "Get ready sweetie." He said and slowly started to press it in.
I squealed as I felt him press in and started to squirm and struggle. He put his arms on my shoulders and said calmly, "Don't wiggle around, it will hurt more. Don't worry, I'm taking it slow." I just nodded and scrunched my face as I felt him keep sliding in. It definitely hurt and I was thinking that maybe I should have started with a guy with a smaller cock. It wasn't quite as bad as I had been scared of though, and it worked in easier the less I struggled. It was hard not to squirm but Joey's weight on top of me definitely helped keep me still. After a couple minutes, he was all the way inside me and said "I'll stay like this for a minute before I start to fuck you." I nodded and soon after he began to slide his cock in and out. I bit my lip but still let out a moan and his cock went almost all the way out, then back in again. As he fucked me, I looked up at this man in control of me and loved the way he looked at me while he fucked me.
After a few minutes like this, he pulled out and moved us to him on his knees and me still on my back but my legs wrapped around his back as he cupped my ass in his hands. I squealed as he put his cock back in me and he said "I know you like it. You're clitty is rock hard. Play with it sweetie. I'm going to cum soon."
I started rubbing and playing with my clitty, as he slowly fucked me. I moaned loudly and knew I was going to cum soon. After a minute or so I came and spurted all over my tummy. He saw me spurt in the air and said "Good baby. Now I need to cum." Thirty seconds later I saw his face and could tell he was cumming. He moaned that he was cumming and I shouted for him to cum in my ass. After he filled the condom up, he stayed in me for a few minutes, lying on top of me. Then he pulled out of me with a pop, and went to flush the condom down the toilet and clean up.
I laid of the bed, my legs spread and cum on my tummy. I was for the first time experiencing the great "just fucked" feeling. Joey came back in the room and told me he had to take off.
"OK." I said. "Do you think we can do this again?"
"Definietly." He assured me. "Next time I need to fuck, you're the first girl I'll call. You have no idea how hot you look when You were biting your lip as I fucked you."
I blushed a little at the complement and since he had referred to me as a girl, and walked him to the door. He kissed me as he left and I went to bed knowing I was no longer a virgin.