Anal Virgin

Molly and I sat there waiting for Dennis. He was a friend of hers. Well, more like an acquaintance. He was roommates with her boyfriend, John and her boyfriend had asked her if she knew any young girls…Dennis like young girls. Even though I was in a relationship at the time, she instantly thought of me because she knows I love older men and would never pass up an opportunity to get something different.

Now, I was a little nervous and being in a bar, I naturally did one of the things I do when I am nervous…I drank. I had about 4 beers and 2 White Russians. By the time Dennis showed up, I was very relaxed an in the flirtiest of moods. He walked through the door and Molly nudge me and nodded in his direction. He was very nice looking for an older guy. He had a shaved head and a goatee which is a look that I find very attractive on a man. I think I just like the sinister look of it. He was muscular and dressed casually in jeans and a t-shirt.

He walked over to Molly and she introduced us. I motioned him over to sit next to me and we started talking. I learned that he was forty-three yrs old, divorced, and worked in construction. The more we talked, the more relaxed I felt. I began touching his knee and leaning into him giving him a look at my cleavage. I never considered myself the “model type” but I thought I looked pretty good at twenty-one with my long dark brown hair and brown eyes. I am about 5’4 and back then was around 120lbs. I even remember what I had on, my favorite black mini skirt and red sweater. He had a few rum and cokes and by midnight, we were both ready to leave the bar and go somewhere more private. He suggested his house.

Molly stayed behind. When we got into his car and started driving, he pulled me closer to him. I kissed his neck and started rubbing his crotch. From what I could tell, he was already getting hard and it felt like I was in for a big treat. At the stop light, he reached down and unzipped his pants and ordered me to suck his cock. That was another thing I liked about Dennis. He was very aggressive and loved dominating me. I leaned down and took his cock out, it was about 7” half hard and I was a bit nervous thinking about how big it would be once he was fully erect. I had never taken a cock bigger than 6 or 7 inches before. I slid it into my mouth slowly, sucking it in and out. He put his hand on the back of my head forcing me to take all of his cock in my mouth. It gagged me a little but my throat quickly opened up allowing the full length to go in. With a few more thrusts, he unloaded into my mouth. I felt his thick cum in my mouth and he wouldn’t let go of my head so I was forced to swallow every drop. His was the first cum I ever swallowed.

When we arrived at his house, he showed me inside. He asked if I wanted a beer and I said yes and asked if I could use the phone. He said that was fine. I called my boyfriend at the time and told him I wouldn’t be home. That I was staying the night at Molly’s. I was lucky that he was an understanding and trusting boyfriend. He said that was fine and he would see me tomorrow. I felt guilty for what I was about to do but I have gone too far to turn back now. And at this point I wanted Dennis so bad, my pussy was dripping wet.

After some more small talk, he leaned in and started kissing me. I felt his hands go up under my sweater and my bra and cup my breasts. He began massaging and caressing my nipples between his fingers. He laid me back on the couch and pulled my skirt up and slid my panties off. He put them behind him on the couch and then started fingering my pussy.

I closed my eyes and threw my hands over my head and just relaxed. Feeling his fingers go in and out while his thumb massaged my clit. He commented on how wet I was and what a nice smooth baby girl pussy I had. He then began licking my clit and sucking it between his lips. I was in heaven. He pushed my legs up and apart exposing my clit even more. As he continued licking me, he slid a finger up my ass. I was surprised as I have never had this done before. It felt so good and he comment on how tight I was.

Dennis suggested that we go upstairs because he thought his roommate might come home and he wanted a little more privacy. He took me by the hand and picked up my panties. I pulled my skirt down and followed behind him as he led me upstairs. We walked down the hall to his bedroom.

His room was light blue. There was a black light over the bed and an American flag on the wall. On his closet door was a mirror. His bed was lengthwise along the closet door, if you were lying in bed, you could see yourself in the mirror. He went to his stereo and put on The Doors. He then shut the bedroom door and lay down on the bed and unzipped his pants and looked at me.

I walked over and sat on the side of his bed and started stroking his cock with my hand. He ordered me to undress him. I walked down to the edge of the bed and took his shoes and socks off and then grabbed the legs of his jeans and pulled them off as well along with his underwear. He then sat up so I could take his shirt off.

His cock was rock hard and huge. He told me to get my clothes off. This was an easy task because by this time, I was only wearing my skirt and sweater. Dennis pulled me on top of him and my pussy was so wet already that his cock easily slid in. I began riding his cock. Fucking him hard, being filled with his cock. He reached up and rubbed my breasts using them for leverage as he bounced me up and down on him. He demanded that I cum now or wouldn’t be allowed to cum later. I looked down at him and began rocking back and forth, up and down like I was riding a horse. My pussy walls began to contract and release and then my hot juices were all over him.

We changed positions and he made it so we were facing the mirror. I was on all fours on the bed and he was standing behind me. That’s when I felt it, the tip of his cock poised at the entrance of my asshole. I backed away instinctively and laid flat on the bed. I told him that I didn’t want to do that, I have never had anal sex before. He leaned down almost laying on top of me. I could feel his breath against my neck and he whispered in my ear to get my ass up in the air. Then he grabbed me by my hair and pulled me up.

He took the palm of his hand and began spanking my ass. Each cheek 10 times. The Doors, Love me two times was playing on the stereo. I begged him to stop. I have never had a man treat me like this before. I was scared and ashamed but at the same time very much turned on. I think that is were my shame came from. He was dominating me and treating me like a whore and I loved it.

After he made my ass red, he poised the head of his cock at my entrance again. This time, I didn’t move. I was on my elbows and buried my head into the mattress. I felt him pushing his way into me, slowly. The head of his cock was in my ass. He ran his hand up my back and put his other hand on my hip. With one thrust, he was entirely in me. I was full of his cock, his balls resting against my pussy. I didn’t move nor did he for several moments. I remember feeling sick to my stomach and somewhat shocked that I had a cock up my ass.

He was somewhat encouraging, saying things like relax baby girl and it would be over soon and start feeling good. I just laid there whimpering. He began pumping his cock in and out of my ass slowly. It hurt like hell. I never felt anything like this in my entire young life. I remember thinking that I wish it would be over soon. I started thinking about anything else other than what was happening to me and the pain I felt. Then, it happened. I realized that the pain that I once was feeling was slipping away and now I was feeling wave after wave of pleasure.

His cock was sliding in and out easier now and I raised up onto my hands and looked in the mirror for the first time and saw Dennis behind me looking at me as well, with his hands on my hips driving his cock inside of me. I started meeting each one of his thrusts trying to drive him deeper into me. It was ecstasy now. I put my fingers in my mouth and licked them then began rubbing my clit. I heard him say that’s it baby girl. I knew you would be into this. He closed his eyes and released his load deep into my bowels. I spanked my pussy and began to cum as well, it was a hard cum and I ended up shooting all over my hand. I had no idea I could cum like that. It was amazing.

He collapsed on the bed beside me. And I lay on my stomach. My ass was still stretched wide open from the recent activities. I looked at him and he kissed me on my forehead and rubbed my back. And so it began…