How I lost my virginity

This story is based on a recommendation from Naughty Eric, hope you like it

I was horny, as usual. I was surfing the web for something to jerkoff to, but I couldn’t find anything that got my juices flowing. All the videos I found were either bad or I’ve seen them before. Have I done this that often? Well yeah, I am a 20-year-old virgin, but I didn’t expect to run out of porn!

I’ve always thought about going all the way with my ex-boyfriend, but I was scared. We met on the football team. You see, I’m a fit bottom with a juicy butt and a tight hole, and he’s more of a bear with a dick so large I am sure it would have split me in half. He ended up breaking up with me because he needed sex, but I was just not ready. The only time I ever tried to give him a blowjob ended so miserably that I wasn’t ready to try again anytime soon. My best friend has been recommending I use Grindr to just find a hook up and get it over with, but I just don’t feel like having my first time with a stranger. I want it to be romantic, I want the guy to guide me through it and cuddle afterwards. Call me stupid, but I want it to be romantic.

That’s probably how I ended up on this random website. It’s a chat service that connects you with other gays, all over the world. So while I pretend I want to be hammered by they big thick dicks, I am safely in my room gently rubbing my hole.

I log in and add “Virgin bottom” as my handle and start swiping through the different guys that were online. I’m into older guys, usually with a dad bod and a small cute belly. I connect with a guy that had a handle saying “Big cock for tight hole”

We start chatting and he suggests we open the cam. I do, making sure my face is not visible. We get it on a bit, I show him my ass, I rub it as he strokes his giant pole. Then I rotate show my hard dick. I’m rather small, a 4incher, but usually guys don’t care since I am more of a bottom. He starts to say weird stuff, and kind of instructs me to “destroy” my hole, telling me to shove stuff inside it so that I feel how nice it is to have his cock inside me and I disconnect. Although this might get me horny, I don’t want the first thing that widens my hole to be an object I find in my room.

I continue searching for random guys, some I don’t like, some don’t like me, until I fall on a 32-year-old with an interesting handle; “Straight but curious”.

We start chatting and he tells me that he was married for about 5 years before they broke up. He doesn’t believe he’s gay, or even bi, but he likes jerking off to tight assholes. Me being a virgin bottom gets him so horny. He asks why I’m still a virgin and I explain my situation. He seems to be nice enough, and suggests we cam.

We start the video and I see his 6inch cock front and centered, now that’s a dick I think I can handle. I show him my ass and he lets me know how nice he thinks it is. As opposed to the previous guy, he asks me to spread my cheeks for him and rub my hole gently with one finger. I can see his dick hardening a bit as I caress my hole. My dick rises to showcase my excitement as he asks me if I would mind inserting one finger in. The way he asked made me feel safe. He seemed like he wanted to take care of my hole instead of destroying it.

However, the thing that ruined the mood was when he asked if I would show my face. He said he’s really interested in seeing the “beautiful face that came with that hot body”. I reply with the standard “I don’t like to show my face” but he insists in the nicest way possible, explaining that he’d move the camera at the same time to reveal his own as well. Skeptical, he then adds that if I wasn’t comfortable, I shouldn’t do it. Weirdly enough, I feel the urge to show my face. He’s treating me in such a nice way that I feel safe showing it to him. I agree, as long as we do it at the same time.

We start rotating the cameras slowly and I can see his belly, then hairy chest, then beard. His view changes from my 6 pack to my chest then to my beardless jaw. We continue to move up and I rush to close the video.

I lose my hard-on as I panic at the sight of his face. I hyperventilate as I realize the mess, I put myself in.

I’ve been chatting with my neighbor.

I’ve showed my asshole to my neighbor.

I don’t know him. I’ve only seen him in the common rooms of the building. I know nothing about him and now he knows how my ass and dick look like.

I turn off my computer as tears rush to my eyes. I feel ashamed and embarrassed. I curl up in a ball on my bed as I rock myself, trying to calm down. In my head, a jumble of bad scenarios fighting to see who wins. I put my hands on either side of my head, trying to calm the storm within me.

Someone knocks on my door.

It’s him, it has to be him. He’s here to continue what we started; except I am not ready to go beyond that. How do I kick him out? What do I do to make him understand it was just supposed to be the online thing?

I put my shorts on and go to open the door, hoping it’s just someone here to sell me some useless thing.

I open the door and I see his face. My eyes tear up as I lose all the words.

“I hope I’m not annoying you by coming over here, but I really need to tell you something. I know what just happened, but you need to know I was just playing. I did not expect to know you and I sure am not willing to do anything except what were doing online. I am straight, and I am planning on staying that way, it was just a game and I need you to know that. I’m not sure what you are into but please don’t mention this in front of anybody else, is that okay?”

I feel my shoulders relax as I hear his words. My tears turn into happy tears as I answer “oh thank god thank god thank god”

He looked surprised so I explain myself, assure him that I was in the exact same situation as he was, and that I was the one who was panicking that he might want something more. He smiles and places one hand on my shoulder as to reassure me, before turning to head back for the stairs.

I turn to close the door and hear him add; “Just…”

I open the door again and he continues “are you really a virgin? I mean I know you said that on the chat, but, is it true? Cause I mean, if you can’t find someone to fuck you, I don’t know who could!”

I smile as he complements me and reply “yeah, I am actually. It’s not that I can’t find someone to fuck me, it’s that I want my first time to be making love and not just having sex, and the guys my age just want to shove their dicks in something…”

He lets out a half “I know what you mean” smile before turning to leave again.

Something comes over me and before I could control it, I blurt out “I was gonna have a beer if you wanna join. I mean, after this, I don’t think I’m in the mood to do that anymore”. I regret it as soon as I had said it. My heart starts to beat faster hoping he says no, but I wasn’t that lucky. He nods and says that he was going to do the same, so why not.

He enters my apartment and places himself on the only couch I have as I turn to the fridge, that’s in the same room of course – damn these tiny apartments – and grab 2 beers.

We chat for a while before he asks what I can only assume was on his mind since he arrived,

“So, if you’re into a romantic first time, why are you on these sites? I mean you won’t find romantic people there”

“Yeah I know, it’s just… I broke up with someone recently, a guy I found and kind of was in love with, but even then he just wanted sex… These sites make me feel a bit safer, there’s a distance between me and the other guy, so if things go in a direction I don’t like, I just close the chat. Also, the things that turn me on online are a bit different that what turns me on in real life”

“Yeah? Like what?”

“Well, online, I like the fantasy of a huge dick fucking my ass, in real life, I’d rather have an average one that will ease me into sex. And a few other similar things”

“Yeah, I guess I know what you mean. For me, I fantasize about a guy’s asshole online while I would never do that in real life”

I feel disappointed, for some reason. I don’t know what I was expecting to hear but hearing him affirming that he’d never do this in real life – which is what I was saying as well – disappointed me a bit.

“Did you not like my answer?” he asks. I get frustrated remembering how easy it is to read my face. Every emotion I have ever had is instantly displayed on my face; the only thing missing is having it written on my forehead.

“No” I lie, “it’s just that… I don’t know… I mean I told you; I was also just doing this for the online thrill but I don’t know… just… don’t know” is the best I could come up with.

He places his hand gently on my knee as he leans a bit closer to me, adding “You don’t have to lie to me, I promise I won’t judge”

I feel something passing through me as if his touch had injected me with a truth serum and I answer “Well, it’s just that you are the first person, online or offline, to be gentle with me. You asked me what I liked and made sure I wanted to do the things you asked of me, as opposed to the others who just expected me to obey”

He smiles as he adds “This is who I am, I’m not into forcing stuff on anyone. But if this is what you like as well, you shouldn’t settle for anything else. There are plenty of guys out there who will make sure you are enjoying sex as much as they are. Search for them”

I feel his other hand circle around me as he rotates to give me a hug. I place my head on his shoulder as his beard brushes my side. I feel something I haven’t felt before and my dick hardens as our hug lingers. Ashamed, I break off the hug and cross my legs, hoping to hide my small erection.

“It’s fine” he says. “You don’t have to hide it” he adds as he spreads his legs to reveal he’s in the same position. “I didn’t mean to, I don’t know what’s happening to me” I tell him.

He places his hand on my thigh this time as he continues to look straight in my eyes adding “Don’t worry about it”

A random feeling of reassurance crosses through me and I lean forward and kiss him. Instead of pulling back, he leans forwards and kisses me harder, forcing me back to the couch as he gently leans on top of me. I feel his dick rubbing on mine as we continue to lock lips. His hands gently caressing my face as we kiss, he breaks off the kiss to make sure I was fine with it.

We continue to kiss for a long time, cocks rubbing on each other through our shorts, until I push forward, leaning back into our seated positions. Me still topless, I remove his shirt to reveal his hairy chest. I start kissing it while he continues to caress my head, guiding me gently, making me kiss his entire chest.

He pulls be back up to kiss me before dropping down to lick my muscular chest. The feeling of his tongue on my nipples makes my dick sprout a little precum. I look down to see it visible on my shorts. “As long as you’re enjoying what we’re doing, stop worrying” he tells me as he catches my eyes focused on my precum-stained shorts.

I stand up and lose the shorts completely. “There, better” I add as my hard cock is freed from the fabric. He does the same, pausing a second to make sure I was okay with it.

He kisses me again, this time both of us standing, our cocks touching as he hugs me and pulls me towards him. I’m a bit taller than he is, and a lot wider. His cock touches my abs and it tickles, making me push my ass backwards and breaking our kiss. “Do you want to stop?” he asks, making me hornier than I was before. I drop to my knees and reply “not at all” as I start to lick his dick.

My only blowjob experience was the horrible one I had with my ex, so I try to start with a lick. I hold his uncut dick in my hand and try to place it in my mouth. “Ouch Ouch” he says as he pulls it away. Horrified I look up waiting for an explanation. “Teeth, don’t use them. Cover them with your lips or tongue”

I abide as I go for my second try. He seems to enjoy it this time. I start to imitate the guys from all the porn I’ve seen as I go up and down on his dick. He lets out a moan, letting me know I’m doing a good job, so I continue with the same movement.

Suddenly he takes his dick out of my mouth. I look up for lessons but the only thing he says was “If you continue like this, you’re gonna make me cum, and I have a lot of things to teach you before that”.

I smile as he lifts me back up to trade positions. I look down to see him on his knees, kissing my dick before taking it whole in his mouth. I enjoy if for a short while before it starts irritating me. He stops as he sees the look my face just made and I explain that I’m not really comfortable with people touching my dick for a long time. He lets go and guides me back to the couch. Still standing, he shows me a new position. My legs apart, torso bent forward, hand on the back of the couch for stability. That’s when he circles back behind and spreads my cheeks with his hands.

“Relax” he says gently while fighting with my clenched ass. I try and I feel his hands separating my glutes. A wet sensation hits my hole as his tongue finally reaches it. He starts by licking and kissing my ass, hands gently massaging my but cheeks. I feel my body relax further moments before he inserts his tongue into me. I clench again before re-relaxing. He continues the movement of licks, kisses and gentle poke until I feel my hole enjoying the sensation. That’s when one hand leaves my glute, and a finger joins his tongue. He continues massaging my hole with his finger while licking around the opening before he pushes a finger inside. He stops, lets my asshole adjust to the sensation before he removes it again and continues the licks.

“Is that fine?” he asks, making sure I was enjoying it. “It is” I answer, rubbing my hardened cock as I further relax my ass.

He continues with his routine until he reaches an upgrade. Two fingers enter me. Instead of pain, I feel pleasure. I let out a shy moan to show my appreciation and he continues to play with my ass.

“I think it’s time for something bigger, if you want. Or we can also just stop now” he says nicely. I take a moment to answer. He remains still, waiting for my verdict.

“I wanna do it” I say, “I’m ready”.

“Do you have a condom? I didn’t think I’d be needing one when I passes by” he says, “Oh and lube while you’re at it”

I head to my bedroom to bring him his requests and notice that he’d followed me in.

“It will be nicer on the bed” he explains.

I hand him the two items and lay on my back on the bed. He sets the condom on the bed and puts some lube on his fingers before meeting my asshole. He rubs the lube on the exterior of my hole before inserting his two fingers back into me, forcing some lube inside as he fingers me.

He asks me to open the condom packet, referring to the lube on his hand, then demands me to put it on him. I feel his dick pumping as I massage the condom onto it, my dick resonating with every pulse.

I lay back on my back. He lifts my legs up, resting each one on his shoulders, before bringing his waist closer to my opening. “You’re sure?” he asks one more time. I nod and he pushes closer to me. I feel his dick touch my ass then force itself inside. It’s bigger than anything I’ve had before. The most I’ve done on my own was put two fingers.

I feel my ass struggle to adjust as he continues to be as gentle as he could. He pulls back out and checks on me. I assure him I was fine, and he repeats the movement, going deeper in this time.

I feel my ass burn and I ask him to stop. He takes his dick out and places his hand on my hole, covering the opening as if to forbid anyone from entering it.

“It’s gonna hurt a bit, but you need to let me go in all the way. Your ass will then adjust, and you’ll be able to enjoy this as much as I am; if not more”

The burning feeling stops so I gesture him to try again. He goes back in. The pain returns but I try to power through. I feel him going deeper and deeper and then I feel him stop.

“What is it?” I ask, wondering why he stopped. “I’m all out of dick” he jokes.

He remains in the same position for quite a while before he pulls back out and goes back in. He stops again. This time the pain is gone. He must have seen my facial expressions relax because he starts to repeat the movement a bit faster. He goes faster and faster until the bed below me starts moving with his thrusts.

He takes his dick out completely and I feel empty. I plead him to put it back in, to fill the void again, and he does. He continues to fuck me for a little while before asking if I would like to change positions.

He rotates me to the side, my legs on top of each other as he fucks me sideways. I feel pain rising again and he suggests we change position.

He lies on his back on the bed and says “do you wanna ride it?”

I jump on top of him, legs bent on each side of him and try to put his dick in me. I fail a few times before he holds his dick, guiding it into me. Once inside, he holds me by the sides and guides my vertical movement. I feel his dick stuffing me and start jumping higher and faster each time.

He reaches out and touches my dick again and asks if it was okay. I enjoy it. He continues to rub my dick with one hand, the other caressing my abs and my chest. I jump up and down on him, his dick reaching deeper inside me each time. I stop and ask if we could change positions.

He turns me around and places me on all fours, my dick dangling between my legs, his dick reaching into me again. This time I feel his dick reach a new stop and I feel a tremble in my body. I feel my hands about to give out and he reached to hold me by my V-shapes. He continues to fuck me as my whole body shivers and I burst my cum all over my bed covers.

Realizing I had just came, he pulls, removed the condom, and burst all over my toned back.

He jumps to get me a towel and wipes my back. I rotate to fall on my side, away from my cum and he lies down next to me. He hugs me as he asks, “Was it as good for you as it was for me?”

“It was perfect” I tell him.

Later that night, I lie awake in bed thinking about what had happened. I was no longer a virgin and it was everything I had hoped my first time would be.