Where it happened: Her dorm
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My name is Matt. I’m about 5’7” 140lbs with a decent build. I play lacrosse so I’m in pretty good shape. It was my junior year of college my girlfriend Abigail (Abby) and I had been dating for like two months. She’s a year younger, wavy blonde with blue eyes. She stands at 5’3” and is exactly 97lbs (I watched her get on the scale one morning). Her tits are super perky with large pink nipples. 32b if you’re wondering. Even though they’re not huge, due to the size of her body they got quite the jiggle to them.
So, my story begins the first night we had sex. Like I said, it was about two months into our relationship. It was around 9pm and I had just finished practice. I showered at my dorm then headed over to Abby’s. She also had practice. Even though she was a cheerleader she was by no means airheaded nor was she a slut so up to this point we only made-out. So tonight Abby finally let me come over to watch a movie in her dorm room. She lived in a suite but her room was a small single. When I arrived she was in a tight pair of grey stretch pants and a surfer-girl tee shirt and her hair was braided in pigtails. As I said, she was not a real slutty girl so she didn’t feel the need to get all dressed up.
She said, “Hi!” kissed me on the cheek then turned to walk towards her bed. I couldn’t help but watch the tight gray yoga pants cling to her perfect ass as she walked away. I had never seen one so tight. She hopped on her bed and asked, “What do you want to watch?” “I don’t know” I responded “I brought a few DVDs if you want to take a look?” I lifted my gym bag. “Ok, lemme see.” I walked over and handed her the bag. “Oh God, this thing stinks!” she said with a slightly disgusted smile. “Sorry” I said, “I just came from practice”. “It’s ok, I’m around it all the time. Our locker room is right next to the guys remember. I always smell it.”
She finally settled on “Transformers 2” (I think she picked it for me since its not much of a chick movie). She went out to her common room to make some popcorn. I just watched her ass as she came and left. When she finally returned I had already situated myself on her bed. I had a tee shirt and a pair of sport sweatpants so I was pretty comfortable. She turned off the light and hopped next to me on the small bed. I was lying on my left side with my right arm over my head. She laid the same way with her ass about where my groin was but we weren’t touching. There was probably 4 or 5 inches between us. Her perfect ass mesmerized me.
About 10 minutes into the movie she said, “This is so fake,” “You picked it” I responded with a smirk. “Well you didn’t give me much choice”. “Do you want to watch something else?” I asked. She rolled over and looked me right in my eyes. “Ok, listen we’ve been going-out for like two months and you good at making-out but are you gonna make another move at some point?” she asked with a bit of a smirk. I was speechless not to mention my dick had already begun to stiffen up from starring at her ass. “Uh, uh I…guess” “Ok”. She flipped back over and wiggled her body towards me. Now we were definitely touching. I thought to myself “Oh my God. Her ass is so tight”. Good thing I had wore briefs otherwise my little man would have been poking her pretty hard.
I dropped my right hand to her right waist. I couldn’t believe how slender she was. I’m not a big guy but she had to be about half my width. As I set my hand on her waist her hips backed into my groin a little and I think I felt her wiggle her ass a little. I couldn’t believe my luck. I was lying in bed next to a hot cheerleader with only a pair of sweatpants and stretch pants separating my hard dick from her perfect tight ass. This was the farthest I had ever gone with a girl. So I was dying to lose my v-plates to Abby, especially since she was hot as hell. As for Abby, I knew from conversations with her that she wasn’t a virgin. She had lost it to her ex-boyfriend over the summer before she came to college. They dated for a year before they did “it” and broke up a few months before they both left for college.
That was nearly over a year ago and she said, “He was the only guy I was ever with.” She did say that they did it quite a bit when they were dating but that only lasted for a few weeks. It didn’t matter because now she was mine and her smoking body was pressed against me. I pushed my hand up her tight shirt. “mmmm…” she whispered. She pressed her hips a little harder against my groin. I dick was rock-hard. I thought to myself, “Buddy you better slow down or you’ll lose your load right here”. Ignoring my thoughts I moved my right hand up to her bra line. It felt like a bathing suit but I realized it was a sports bra. I pushed my fingers underneath and felt the most amazing thing. Her tits were so soft but firm at the same time. By now we both were ignoring the movie. She rolled to face me and placed both arms around my neck. I could feel her pressed against my groin as she pressed her lips against mine.
I removed my hand from her shirt. She sat up and pulled her shirt off revealing a light grey sports bra that seemed too small for her perky breasts. She reached for my tee shirt and pulled it over my head. She lay next to me and we continued to make-out for a while longer. I felt my dick getting ready to burst as the bare skin of her flat abs touched mine. “God you’re so hot.” She said. That was it; I finally mustered the courage to go the next step. I sat right up and slowly reached for the waistline of her tight yoga pants. “Wait.” She said. “You know I’ve only been with one guy, I don’t want to think I’m easy.” “I don’t” I responded with a smirk (not that I cared at this point since by dick was ready to burst).
I pulled down her pants to see a tight pair of pink striped bikini panties. She sat up reached for my waistline and did the same. I was wearing a pair of tight brief trunks with a pretty evident bulge from my dick straining against the fabric. She lay back down and I leaned over her. My hard, brief constricted dick briefly brushed her equally covered tight pussy. I pulled her bra over her head. I throw the bra to the floor and she sat back as her tits jiggled. I thought, “Wow.” Her boobs were perfect. She had a small birthmark on the inside of her right breast towards the center of her chest and her nipples were perfect. She had slightly “puffy” nipples that stuck out around half an inch. I thought, “How could her ex let her go!”
I reached for her panties and pulled them to her ankles. As she kicked them off I starred at her pussy. Either she shaved or was completely hairless. Maybe it was because she hadn’t had sex in 10 months but her pussy looked so tight. I held my balance with my left hand on her small mattress and with my right I placed a few fingers against her now slightly swollen pussy. “Ooh.” Was all she said, and then I started to push my finger in. Being totally inexperienced, I had a hard time at first but finally I found the way! “Oh my God! She is so tight!” I thought. I felt as though my finger was being pulled into her pussy. I by no means have a big dick but I was beginning to wonder whether I would fit in her. While I was thinking this it occurred to me that I didn’t have a condom. “Great” I thought to myself. “The one night that I could possibly get laid I don’t have a condom.”
I pushed and pulled my finger in and out of her tight pussy. “I forgot a condom.” I said to her with a sad tone. “Oh.” She said looking a little disappointed. The mood got kind of awkward so I slowly pulled my fingers out of her pussy. As my fingers exited I think it snapped back shut because I felt some of her juice hit my hand. She sat up on her elbows, her perfect tits facing me. What was she going to say? Maybe she didn’t even expect to have sex with me tonight. Did I go too far? “Well if you’re not too weirded out. I still have a condom that was my ex’s. He left it here a few days after I moved in and I think there are a few left.” Weirded out? Heck, this guy was my savior!
“Uh, ok. Where is it?” “Um over there in my desk drawer, the second one from the bottom.” She responded. I hopped off the bed a little faster than I should have but I was too boned up to slow down. I opened the drawer (second from the bottom) and shuffled around for a sec. “Did you find it?” she asked. I thought to myself, “Please be here, ah here it is.” I could feel the individual foil packages. I picked up a few but was a little surprised. It seemed bulky and I looked closer since the only light in the room was coming from the TV. “Did you find it”, she repeated. “Yeah, I think I got it” I said. “Great.”
As I peered at them I realized that this condom were in gold foil and designed for a much heftier dick than my own. It was large sized. “Well are you coming back to bed?” she inquired slightly annoyed. “Yeah, I’m just checking the expiration” I lied. Just my fucking luck, I’m about to lose my virginity to a hot cheerleader but the only condom I have belonged to her horse-dicked ex boyfriend and she probably has no idea that he has a big dick and I have an average one. Great.
I turned and hopped back onto the bed. “Do you want me to put it on you?” she asked. “Uh, no I think I got it.” I said. “You’re not weirded out are you?” “No, why would I be” I lied. “Well, it might be weird to use your girlfriend’s ex-boyfriends condoms. Not that it really should matter your both guys and they don’t have his name on them” I thought, “Did she just say that I am her boyfriend? Awesome!” There was a glimmer of hope followed by a crush to my gut; she has no idea that her ex was big down there.
“Ok, are you ready? I am dying here.” she said with a hungry look in her eyes. This was the moment of truth, may be I could slip my briefs off and the condom on fast enough so that she doesn’t even see. Here goes nothing. I slipped my shorts off and tossed them on the floor. My hard cock sprang to attention, point almost to the ceiling. I quickly glanced at her face and I sensed a moment of surprise. She just smiled and laid back. I opened the foil and removed the condom. I set the open package on the dresser next her small mattress then began to unroll the over sized condom on my 6 inch dick. It wasn’t so much the length (don’t get me wrong it was way too long for me) but I was the girth of the condom that made it look ridiculous. There was so much extra room it felt like a bag over my dick.
“Ok, are you ready?” I asked. “Uh huh.” She whispered. Balancing my body with my left hand I held the condom tight against my dick with a few inches of condom flapped over the base of my steel hard dick. I thought to myself, “How could I guy fill this thing?” I pushed the head of my dick against her moist pussy. She was still tight. I maneuvered for a good 5 minutes before I began to enter. She winced a little. She was so tight even though the condom was loose I could feel her pussy gripping my hard dick. I got about 3 inches in when she spread her legs even wider. “Ok, please don’t go much deeper.” she whined. “Alright.” I said. I pushed a little more, 4 inches, then 5 inches, 5 and a half then the head of my dick hit something. “Oh my God, pull out a little your hitting my cervix.”
“Seriously?” I though to myself, “How on earth did her ex screw her? She is already asking my to pull back?” Then she said, “Sorry, you’re really deep. Could you go easy?” I asked, “Ok, but what did you do last time you had sex.” Annoyed she responded, “Well, it hurt a lot then too. Just go easy.” Then she set her head back on the pillow that she was gripping with both hands over her head. I just left the head of my dick against her cervix for a second, savoring the moment. I thought, “Wow, I’m actually so deep in a girl that I am hitting her cervix. Maybe this isn’t going to be so bad.” She began slowly rotating her hips on my hard dick, massaging her cervix on my head.
Teasing her I started pulling and pushing a quarter inch at a time just enough to tap her cervix. “Oh, oh.” She whispered. The little bed started to squeak. “Please go slower, my roommates will here us.” She said between moans. I pulled out further this time, this time about an inch then I pushed back in. “Oh.” She whispered through her clenched teeth. Again I pulled out two inches and pushed it back in, I did this a few times the I realized that my dick was not sliding in and out of her tight pussy but in and out of her ex boyfriend’s over-sized condom. Just as I realized this I pulled out three inches and noticed that less of the condom was on my dick. It now only covered three quarters of my hard on.
I stopped thrusting and held my dick by the base with my right hand and with my left tried to pull the condom back but it was stuck inside her tight pussy. “What’s wrong?” she said while breathing heavy. “Nothing.” I lied again. She laid back and started to lightly rotate her hips. “Shit!” I thought. I slowly pulled my hard dick out, gripping the base of the condom at the same time. My dick popped out of her tight pussy along with a lot of juice, a second later the rest of the condom followed. “What’s wrong?” she said as she sat up. “Nothing. I think the condom broke.” I lied.
“Fuck!” she said. I had never heard her swear before. “I’m sorry.” I said. “It’s ok but I’m so turned on do you want to try without one?” I thought to myself “Hell yes!” I responded, “Uh, ok if you’re cool with that.” She smiled, “I am, and I’ve only done it with one on so everything should be cool. Right?” “I’m sure it will be fine” (Not that I cared at this moment). I threw the over-sized condom to the floor and leaned over her. I put the head of my hard dick against her tight pussy.
It was so warm. I pushed in. She moaned much louder this time. “Oh my God, it feels so much better without one!” That it did. I pushed hard. “God, she is so tight.” I thought. I pushed all the way to her cervix when she winced and then I began to pull it all out. I looked down as I drew most of my dick out; her pussy was clinging to my dick as a pulled out and again as I pushed in. I did this about three times before I felt my nuts begin to tight. I was about to erupt. By the fourth slow thrust I had to pull my dick out. “I’m sorry.” I said. I frantically jerked my dick with my right hand. I felt the cum build up then it happened. I started dribbling cum all over her sheets. Four, five, sex drips poured out of me. Then I let go of my dick and looked up at her. She looked disappointed.
“I’m so sorry.” I said apologetically. “It’s ok. It’s your first time.” She said. She reached for her shirt and pulled it over her head. I reached for my briefs. After a few minutes we were both fully clothed. The rest of the night was uneventful. I was embarrassed and I think she was too. As we held each other in bed, she said, “I was surprised at how good it felt without the condom. I should have tried that a long-time ago.” I thought to myself, if that had happened she probably would still be with that horse-dicked high school sweetheart.
As our relationship progressed over the next few months so did our sex life. We started screwing every day. Sometimes in between classes and since our experience our first night together we didn’t bother with a condom again. I practiced the art of pulling out quite regularly and she seemed to be enjoying my dick. I wasn’t sure if was cumming and I didn’t want to ask. Life was great but nothing could prepare me for what happened next.
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