My[F] first anal experience, while his roommate slept on the bunk bed above us [MF]

Hello gwstories readers! I’ve been lurking on this sub for awhile, and I’ve definitely gotten off to a good amount of stories. I thought it’d be fun to share one of my own! So I made a throwaway and waited 24 hours to post. Fake names are used and all that jazz. I know some people like long background and some just like the dirty dirty. Skip to below if you want the wham bam thank ya ma’am.

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This story takes place 6 years ago while I was a sophomore in college. Because imagery seems to be so important here, I’ll do my best to paint out what I look like. I’m half Filipino and half Chinese with tan skin and black hair that was fairly long at the time. I’m only 5’1 and weigh around 100 lbs. (Do these stats really make a difference?) I barely fill out a B cup bra, skinny but not the most toned, and not completely flat I’ve got a little booty I’m proud. I worked my ass off for it. Get it?

I was in a relationship with my then boyfriend for almost a year. Nick is white, 5’10, and pretty damn good looking. He had islander blood in him as well, and he kept up with the gym daily. He had an 8 inch cock. Lol, jk. He wasn’t impressive and just had a 6 inch cock only but very thick. Lol, again, why do so many stories say this like 6 inch and thick is below average? Honestly his cock is around 4.5-5 inches, I think? It constantly rocked my work though. And honestly? We ladies don’t care as much about size as you think, as long as you know what you’re doing.

Alright, now that I’ve spent two paragraphs just describing what we looked like so you can have the most efficient fun imagining the story, let’s get on to the story! I had only slept with one other guy before Nick. My hs boyfriend and I kept it pretty vanilla. But Nick loved exploring different kinks with me. And honestly I loved all of them, except I was really scared about anal. He would use his fingers to rub my asshole sometimes, and other daring times he’d push a finger in while I was too distracted by the heat of the moment. But whenever he would try to push himself inside, I would say no. Though he was a kinky fucker, he was a gentleman and never pushed twice in the same time and he’s happily continue other things. We had a conversation where I told him I would want to work up to it slowly, so that’s why he still would try and play around. But every time I’d always get too scared and say no.

We met in class our freshmen year, but then he transferred to a different school the next year, but it was still in the same city. I was living in an apartment with two other girls, and he was required to still live in the dorm. We would always spend time at my place, and he’d sleep over often. I only ever visited his dorm rarely, maybe just because he needed to get something and we were already together. At the time, I had two roommates and I was close to them both. One of my roommates, had a lot of family coming over for an extended weekend. Her family was coming in from far away, and they don’t get to visit often. She was planning on getting them a hotel or Airbnb for the weekend, but why spend money why you can save it? I offered my room for the weekend, and asked Nick if we could sleep in his dorm for that weekend. He was a little sad because he doesn’t like not having privacy, but he did not hesitate to say yes.

Friday night, Nick and I arrive to his dorm. He’s really close with his roommate, Adam. I like Adam a lot too, he’s been over to my apartment and we go out with him a lot as well. Nick asks Adam if it’s cool if I sleep over this weekend. Adam says “yeah, man, of course it’s no problem.” I smile at him and Nick says “thanks, just let me know if you ever feel awkward and we’ll figure something out.” See, Nick is such a sweetheart. We have a pretty chill Friday night with Adam and a few other friends just hanging out in the dorm playing Super Smash Brothers Melee (does anyone here play ultimate?) and maybe watched a movie or something. The night comes to an end and both Adam and Nick are in their own beds. They’re both just wearing boxers, as they both discussed they can’t sleep wearing more clothes. Though I usually only sleep in panties or just a T-shirt, I was still too shy. But I did sneakily slip off my bra in the dark and shove it into my bag.

Nick spoons me and plays with my hair. I feel him start to push himself up against my ass, which always happens minutes after spooning. I grow very conscious of Adam in the bed right above us. It makes me nervous and not exactly in the mood. I can feel Nick start to get harder as he pushes against me more and more. I get nervous that the blanket is making too much noise and quietly ask Nick to wait a little longer. He stops moving and I relax into his arms.

I’m relaxing for just 10 seconds when Nick brings his hand on my stomach, underneath my shirt. The skin to skin contact immediately excites me, even more so that I know where that hand wants to go. His sexy fingers dance lower and lower until they’re resting right above my pussy. I anxiously wait for him to move to where I need it. And then stop his hand movement and he hugs his body closer to me.

“Goodnight, baby” he whispers softly to me. Being a fucking tease. He wants me to want it, even though he knows I’m so nervous that someone is literally right above us. But the light snores we heard from Adam were very encouraging.

The fucks that I had slowly started to disappear, and I grinded my ass ever so slowly on his cock. As we were laying on our sides, I’m limited in my motion. But I did my best to sway back and forth on his cock. I was rewarded with a very hard dick on my ass.

The hand above my pussy hastily made it’s way down and met my clit eagerly. Nick pushed his thumb lightly against my clit, exactly how I liked it. He teased this area a few more times and then his fingers wandered lower to my soaking wet pussy. His other hand found my waist, and he dry humped my ass even harder. He then slipped one finger inside of me, quickly followed by another finger. Nick finger fucked me in the exact spots that drive me crazy. He didn’t go as fast or as hard as we were still trying to be quiet. But right when his thumb found my clit again, I came hard around his fingers. I felt Nick pull out of me, and while I was recovering from my orgasm, Nick but his two fingers in my mouth forcing me to taste my own juices.

The next thing I know, Nick is slipping my panties and shorts down quickly. He pulls me close to him, and then his cock finds my pussy and slides in easily from my juices. He has one hand on my hip, and the other is back in my mouth. He starts to fuck me faster, and the blankets are definitely making noises. We still hear some snoring, and actually thinking about Adam above me turns me on even more. My boyfriends cock is inside me and another guys is literally right there. It made me so wet and crave for Nick to fuck me harder. The hand that was in my mouth he moves to my throat. He chokes me (lightly, and definitely within the limits we’ve set) and continues to fuck my cunt. I cum hard on his cock. He let’s go of my throat and I cover my face with his pillow to mask my heavy breaths from my orgasm and not being able to breathe. He continues to fuck me while I try to catch my breath. I’m extremely wet, I felt like we were fucking in a huge puddle of my juices. I’m loving every moment of it. Even though I’m still coming down from my high, the excitement of the secret fucking gets me excited all over again and as he keeps fucking me I feel myself reaching another climax. Until Nick pulls out.

I thought Nick was teasing me. As he pulls out his hand rubs against my thigh and he puts it back on my mouth, making me see how wet he’s made me. I need his cock back in me, especially after tasting myself and feeling him rub all the wet against the backs of my thighs. His free hand plays with all the wet and I feel him try to gather some in his fingers. The next thing I know, he’s pressing those same fingers around my asshole.

I almost squeak out in surprise. But it starts to feel good. Maybe from how incredibly wet I am and how turned on I am with Adam so close. Nick pushes one finger inside of me, and I have to again force my face into the pillow. In the past, Nick usually puts another finger in, to help me get ready for his cock. But this time was different.

He takes out his finger, and it’s suddenly replaced with the tip of his dick. Before I can even process it, his cock quickly slides halfway into my asshole. It slid in quickly from how wet I was, but my asshole definitely wasn’t used to it. I have no idea what to think or feel. I’m nervous and scared for the pain and horny and excited at the same time. He pushes more and more slowly until he’s all the way in. I try not to scream into the pillow. He whispers, “are you okay?” and in my head I nodded or showed some sort of sign of approval. He tries to pull out, and this motion hurt like fuck. I grab some part of him in an effort to tell him to wait and slow down. We do this for awhile until I start to kind of get used to him. It’s still more painful than pleasurable, but I’m still so horny. I start to get turned on thinking how good it feels for him having my tight asshole around his cock, something’s he’s been desperately wanting. He continues to fuck me, and it starts to feel a little good. Then he starts picking up the pace. And then we hear a loud shift in the bed.

We stop our motions completely. My heart is racing and I’m scared but also I kind of maybe want to get caught? We wait and listen for more movement. A few moments later, we hear a lot more movement and Adam is getting off of the bunk bed. He then walks to the door and heads to the hallway. I have no idea what to think, if he went to the bathroom or if he knew and let us be? But the moment the door closed, Nick rams my ass hard and starts fucking my ass hard and fast. I let out a moan and start to enjoy being used like a slut. Nick’s cock feels amazing in my ass. But just s few minutes later we hear the door open and we completely still our movements yet again. Adam climbs back into bed. I think all of Nick’s fucks are completely gone and he starts to slowly fuck me quickly after. I stop caring as well and I bring my hand to my clit and start to rub like crazy. I can’t even think, my mind is completely gone in the moment. And all of a sudden, I feel Nick’s cock pulsing in my asshole as he fills me up with his cum. Knowing this, i cum instantly while he fills me up.

He slowly and gently pulled out of me, and slipped my panties back on for me. He kisses me and tells me he loves me and I fall asleep before I can even respond. I’d soon learn to love and crave anal.

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I say “then boyfriend” because he’s now my fiancé. He’s also given the okay stamp of approval for this to be on reddit! We have some other fun stories as well, like I said he’s kinky as fuck. And I have some stories (all of which he’s heard and loves listening to) from our long break too. I hope you enjoyed and it’s up to the gonewildstories standard!

Source: reddit.com/r/gonewildstories/comments/avlnci/myf_first_anal_experience_while_his_roommate