u/Actual_Feedback2725

▲ 37 r/ShareSexStories+1 crossposts

My (24m) first time ever with a girl (24f) in my dorm room (both 19 at the time)

My freshman year of college was during covid. So everyone had their own rooms but still had to share a bathroom/shower room. Anyway, I was trying to settle in and figure out how I was going to navigate school during the pandemic.

Flashback to about a month before the world shut down, I attended an orientation of sorts for incoming freshman. I got to meet other people with the same or similar majors. I’ve always been pretty socially awkward. I’m 5’ 11” and at the time I was about 300lbs. So I was definitely self conscious. But anyway, there was this girl. For the purposes of this thread I’ll call her Sierra. The moment I saw her I just knew she was the one. I know that’s crazy, but I was a 19 year old virgin who’d never even kissed a girl. So I get an opportunity to meet her and we have a nice, brief chat before we have to move on. I had been so caught up in my feelings that the blood pounding in my head blocked out her name. I was so upset that I wouldn’t get to see her again until classes. (About 6 months from our first meeting.)

Flash forward about a month, and I receive an email for all the freshman to fill out in my department as a little get to know you thing. They were going to post blurbs about us on social media and what not. I knew this was my chance to find her and maybe just Instagram stalk her a tiny bit. I finally found her name on the list and found her Instagram. I didn’t want to be weird so I added her and a bunch of the other freshman that I found to a group chat. We all talked for a bit, but then I got a separate notification that she had sent me a private message. We talked about meeting at the event and what classes we would have in common. Eventually, she gave me her snap and we started talking every day from then on.

Jump ahead to move in day. We made plans to grab lunch together and eat in the quad so we could talk in person. We met up and had lunch and instantly hit it off. We sat under a tree just talking for about 3 hours before we decided to part ways for the day. We of course kept texting each other, but I couldn’t wait to see her again. She sent me a few pics of her dorm setup and I sent some back but also playfully said “pictures don’t do mine justice”. She told me she’d come over that night to check it out and that we could watch a movie or something. I started panic cleaning even though I had nothing to clean since it was my first day there.

That night she told me she was ready and I gave her my room number and she came over. I had a pretty small room, so there wasn’t really any space for extra chairs or anything, so we both sat on my bed. We put on some movie on Netflix (I genuinely cannot remember what we watched I was so nervous). My heart was racing and we were sitting with about 3 inches in between us. I tried to pretend my focus was on the movie, but I was lost in her vibes. We were probably 15 minutes into the movie before her hand left her thigh and settled in between us. I wanted to immediately put mine on top of hers, but I held back. I was nervous I would do the wrong thing. About 5 more minutes passed and I finally got up the courage to slowly move my hand closer to hers. I slowly shifted it towards her and as soon as they touched, she grabbed my hand and interlocked our fingers. She scooted closer to me so that our thighs were now touching. I looked over at her and she looked at me and smiled before leaning her head on my shoulder.

We stayed like that for about 10 more minutes before she pressed her foot against mine. Our hands were interlocked still, but they were resting on her thigh. I slowly started grazing her thigh with my finger (not in a sexual way, but in a caring way. Or so I thought). She picked her head up and we looked at each other and stared deeply into each other’s eyes. I wanted to kiss her so bad but I had no experience and was scared I’d do it wrong. After a few more moments, I think she realized I was petrified and asked “would it be okay if I kissed you?” I could only nod. We closed our eyes and locked lips. I SUCKED. Her lips were so soft but mine were rigid and I knew it was bad. She pulled away and chuckled a bit before putting her head back on my shoulder. I was so embarrassed, but I knew that it was something everybody had to go through at some point in their life.

After another 10 minutes or so, she lifted her head again and looked at me and said “your heart is beating really fast I can hear it on your shoulder.” I didn’t know what to say so I just said “sorry.” She thought that was cute I guess and told me that it was okay and to relax. I took a deep breath and closed my eyes for a second and when I opened them again, she went in for another kiss. This time was different. I don’t know what changed after the first time, but I was more relaxed and our lips were soft together. It was like kissing clouds. Our slow mild kissing started to get a bit more heated and somehow when we came up for air, the movie was over. She laughed about it and asked if I wanted to put something else on for background noise. I picked a random movie and then realized what she had just said. “Background noise?” Damn I was naive.

She didn’t even respond. She slowly pushed me onto my back and got on top of me and we started making out again. She told me that I shouldn’t be afraid to explore her body, but I didn’t know where to start to I just started running my hand up and down her thigh and across her back. After a minute or so, she grabbed my hand and guided it over her shirt. “Try this.” She didn’t have to tell me twice. I palmed her boob in my hand and started massaging it. It was so soft.

Sierra was a small woman. She was about 5’ 2” and super slim. Her ass was big strictly because of how small the rest of her was, and her boobs were that amazing size that fit perfectly in your hand.

Anyway, we’re making out and I’m touching boobs for the first time in my life (over the clothes, but still). She runs her fingers through my hair and then tells me to grab her waist. I do and suddenly she starts grinding her hips on me. I think I was too nervous to get a boner before that moment, but when she started swaying her hips, by dick grew hard almost immediately. I was wearing jeans that were a little tight, so my dick was pressing against them at a weird angle that wasn’t comfortable. I told her and she said “oh no. We can’t let that happen.” She repositioned herself at my side and we continued to make out while her hand traced over my chest, then my stomach, and finally just above my pants. I involuntarily arched my back a bit and pressed my hips into the air a tiny bit. “Someone’s excited.” I was embarrassed again, but then realized that I was about to have sex and who cared? She slowly moved her hand down further and further. When she reached the bulge of my cock pressing against my jeans, she let out a seductive moan like it was the biggest dick she’d ever felt. My dick is about 5 inches, so that moan gave me a boost of confidence that I hope everyone with a penis gets someday.

She rubbed the outline of my cock and moaned in my ear. We started kissing again while she undid my pants with one hand. It took her a second, but when she did, my dick sprung up in my underwear. She pulled my pants off so I was just in my boxers and teased her fingers around the inside of my thighs. She then asked me if it was okay if she reached into my underwear. I of course said yeah. She traced the rim before sliding her hand in. The sensation was immediate. She wasn’t even touching my cock and I felt things I’d never felt before. Her hand danced around the edge of my pelvis before finding its way to my balls. She cupped them and started massaging them while we kissed deeply. I started twitching a little bit and she thought that was hot and kept trying to make me twitch even more. After what felt like forever of her focusing on my balls, she finally made her way up to my shaft. She didn’t tease me this time. Instead, she gripped it and started stroking it slowly. I was in heaven. She stroked me for about 5 minutes while we made out before she asked me if I wanted to try touching her. I told her yes and she laid on her back while I leaned on my side.

She took my hand and this time placed it under her shirt. She had on a compression shirt underneath, so I still didn’t have the best access, but she quickly took off her main shirt and then pulled up her compression shirt revealing the most beautiful pair of tits you’ve ever seen. Like I said earlier, they were the perfect size to fit in your hand and her nipples were perky. I stared for a minute dumbfounded by the first boobs I’d ever seen in person before she told me to kiss them. I immediately did. I put her nipples in my mouth and sucked just a little bit. Then out of nowhere I decided to bite them gently. This drove her crazy.

We continued this for a while longer and then she took my hand and guided it down towards her upper pelvis. I got nervous again and she told me it was okay. I slipped my hand under her pants and panties and to my surprise, she had shaved completely. My shock only lasted so long because my hand was steadily approaching her vagina. I slowed up and started feeling around slowly until my finger slipped into a wet area. She let out a soft moan and I took that as my doing something right. I started to rub a bit more and work my way around until I found an opening. I slipped my finger inside of her and she quivered a little bit while moaning for me to keep going. I slid my finger in and out before I remembered I should be looking for the clit. It must have been beginner’s luck because I found it immediately and started gently gliding my finger across and around it. Her soft moans grew into a pant as she gripped the bed sheets tight. Her moaning grew louder and I felt like my neighbors would be able to hear, but I didn’t care because I was making a beautiful woman orgasm. Her body tenses up a bit and I felt her clit pulse as she let out an uncontrollable sigh and started shaking. I softened my touch and we kissed as she rode out the rest of her orgasm.

She moved my hand to her ass and I pulled her in close to me while we made out some more. My dick was still hard and was pressing into her side. I apologized for some reason and she said “you don’t need to. One, it’s natural, and two, if we were doing what we are doing and you weren’t hard, that would be a problem.” I laughed and as another response, she reached down and rubbed my dick over my underwear. I immediately quivered again which only turned her on more. She pushed me onto my back again and scooted down the bed. At first I thought it was to have a better angle to take my boxers off, but I soon found out she had something else in mind. My boxers were now off and she just kinda looked between my cock and my eyes with what felt like pure admiration. That honestly turned me on even more and I think I grew to about 6” at that point.

She started teasing my inner thigh again, but this time instead of her hand, her lips and tongue were kissing and licking from my inner thigh towards my pelvis. I quivered a tiny bit and she got so excited that she skipped from the bottom of my balls directly to my tip. Her tongue circled softly around the top of my shaft. She pursed her lips and slowly made her way down my now throbbing cock. I have never felt anything like this even since. It was so warm and slippery and it felt so incredibly good. I just laid there with my eyes closed for a minute or two before realizing that I should be watching. I looked down and saw her staring back at me somehow smiling at me with my dick in her mouth. She stopped sucking and made a show of it for me. She sucked on my balls a little bit before licking her way from the bottom of my shaft all the way up to the tip. I was leaking a bit of precum at that point, and she seemed to take that as a challenge. She went back to work gliding her cloud-like lips and tongue up and down my dick.

I don’t know if it was the first time nerves or something else, but I just couldn’t seem to finish. She alternated between sucking my dick and jerking me off for about 15 minutes before she decided that maybe we were gonna have to go a bit further for me to cum. I told her I didn’t know if I was ready yet, and she said that was okay and kissed me for a bit and continued to stroke my cock. After realizing that I didn’t think I was going to finish this way, I told her that I might as well just do it. She smiled and said that she didn’t think to bring any condoms. Luckily, my brother had gone to a club and pocketed a shit ton of condoms from the bathroom and gave them to me as a college present. I grabbed one and she told me she’d put it on me.

While I took my shirt off, she opened the condom and set it on my dick. She slowly stroked me and pushed the condom down over my shaft. It was honestly kind of a tight fit. I was shocked at how turned on I must have been. Once Sierra was satisfied with her work, she laid on top of me and kissed me a few times before straddling me and positioning herself above my anxiously awaiting cock. She squatted down and my tip slid smoothly into her then she lowered a bit more and my whole dick was inside of her. We both moaned into each other’s mouths and stared into each other’s eyes while we adjusted to this new feeling. After a moment, she rocked forward and her pussy gripped my cock before she rocked back again. I was stunned by the feeling and held onto her upper back to go as deep as I could. She started to speed up a little bit and the sensation was almost overwhelming. I started raising my hips to meet hers when she rocked back. I slowly started to take control from the bottom and got more confident. I cupped her boobs and focused on her nipples. While I did that, I felt her tighten around my cock and then she suddenly shook again and moaned louder than she had before. Her tightening around my shaft was enough to send me into overdrive.

When she had desensitized a tiny bit from her orgasm, she started riding me again and I took the opportunity to thrust myself as well and within a few seconds I could feel myself building. I told her I was close and she locked in. She leaned back and played with her tits and sucked on one of her fingers while maintaining eye contact. I had my hands on her hips and was pounding as deep as I could. About a minute later I was ready to cum. I told her I was going to and she leaned forward and whispered in my ear “cum for me.” I thrust a few more times and then exploded into the condom. I had never had such an intense orgasm. She continued to grind her hips a bit more to squeeze out every last drop. We kissed while my dick began to soften inside her. It slipped out and I took care of the condom. While I was tying it up, she kissed down my stomach and put my dick back in her mouth and sucked all of my remaining cum off. She crawled back up and we spooned for a bit (her as the little spoon) until we fell asleep.

The next morning I woke up still naked. She was still asleep but her ass was pressed against my dick and it was so hard again. But that’s another story.

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u/Actual_Feedback2725 — 16 hours ago