How I got my best friend to lose his virginity [MF] and got laid with an incredible MILF on the same night [MF]

Time flies when I look back, but this is a proud moment for me. It was Tommy’s 21st birthday party, and the boys and I [M20] got a proper celebration plan in place. I was still roughened up by finally putting an end to my love affair with Susan, Tommy’s mother, and it fucked me up when I understood that she was back to her old ex – but, as I said, Susan is a closed book. Today is about Tommy, but also about myself and the first time I also got properly laid after Susan.

The time between breaking up with Susan and Tommy’s 21st was spent focusing on getting Tommy, shy and anxious, to a new level of confidence. He joined a local amateur football club after my suggestion, and the time I was around we’d go running together. That last week of June just before his big day was spent hitting the dumbells and crunching some abs, but he was still my Tommy, the same slim dude I met all my life. The afternoon of his 21st we went to get the same buzz cut, and that night, we hit the town (whatever that means to you).

We were like six or seven guys, all in the same age range, early twenties, and eventually, we met with a few other groups of friends. I haven’t been entirely honest with Tommy at this point, because I knew Monika [F20], a crush of his, was going to be there at some point. I talked to another girl, and we got this plan together – to get them in the same disco and kinda force one into the other -, and I felt like a matchmaker. Now, I had to match them without looking too obvious. Prior to this, said girl was also weaving a web of how handsome Tommy was becoming, while I kept mentioning Monika to him, casually, and watching him blush. All in all, we were certain that the level of interest from Tommy somehow matched Monika’s.

We got together and went from one pub to the other, Tommy was really happy, and I got worried because I didn’t see Monika or the other girl – the second pub was supposed to be the place. He knew I was texting someone and kept asking what I was doing, but I kept avoiding the topic. The other girl texted me back, saying Monika wanted to go to a club, and I was like, that shit will get expensive, but anything for Tommy, am I right?

Told them to gobble down their drinks and look presentable, and wished that the security at the door would let a group of seven dudes storm into his nightclub. Sometimes you are lucky enough, and the guy at the door was a friend of a friend, and it wasn’t that late yet. It’s dark, lights throbbing all over, loud music, and a shit show of corpses floating in front of us like zombies.

I finally found the girls, and Monika was there, they were all dancing in a circle, but she was looking straight ahead. And holy fuck, if looks got you laid, we would be fucking right there and then.

You see, Monika tried to flirt with me before, but I was only interested in Susan, and never let things escalate, and since I knew Tommy had a crush on her, I always kept things as straight as possible.

Suddenly, Tommy punched me in the arm, like, fucking hard, “this is not a random encounter,” he yells at me, and I just laughed it off. “Dude, relax.” God, took him a while to relax, and at that time, I thought my move was a dick one. Well, it fucking was but seemed to be my signature. Our groups kinda mingle, the music flowed, I got him a beer, we all danced, and the night seemed to be going fine. I talked to the other girl, and just waited and watched as our soon-to-be couple avoided themselves.

Tommy and I went to piss, and he told me how I fucked things up, but I reassured him, “dude, you already have the no. She’s fucking yours, bro,” but he insisted, saying she wanted me, not him, that she was looking at me, not at him, that I was taller, muscular, cute, in the army, and got a big cock.

He was clearly looking while we pissed, which is a no-no in my rule book. I had to stop him, and used my untested psychology on him – a sort of braveheart speech, but much worse (things sound better with alcohol though) – it’s not about the size, I did peek over and he looked perfectly average to me, and I told him that, I’ve seen plenty of cock in the army, no concerns about his. Believe in yourself bro, that was the sum of it, and now we were going to get back there, and he was going to conquer her for the night.

As if things were this simple.

Monika made a move, but towards me, not Tommy. He got that right. When I think back on this scene, I think of that song by Madonna, “time goes by so slowly”, but probably not accurate, but she was dancing, and moving more toward me, and I moved Tommy into her way, but she got in between us, hands around my neck, while I tried to be polite, and move her away, but she whispered things like “missed you” and stuff like that.

I thought it was unfair. Tommy was getting the most attention ever from the other girls, he wasn’t making a move because he loved Monika, and here she was trying to get frisky with me.

“You didn’t miss me,” I tell her, but she pouts, “you’re so damn cute,” and I tell her Tommy is cutter, so much cutter, and I watched him starting to get really pissed with me, so I grab him by the arm and get rid of her arms around my neck, and despite not wanting anything with her she was getting me hard already, and that was fucking dangerous.

“Listen, Monika, I will only break your heart without thinking twice. Tommy here, he is husband material. I’m a motherfucker.”

She giggled, Tommy looked at me as if he was saying “bro, it’s fine,” and I felt like I was a fucking curse to him, and for sure it couldn’t be true. Tommy is so beautiful compared to me. I have stature and confidence, but Tommy has a heart of gold, a soul, he’s handsome, and he was getting stronger, even I could see the man in there, while Tommy still needed a confidence boost.

“What if I want you?” Monika asked, teasing, and I told her, “You’d better fuck off. I’ll break your heart and laugh about it.”

The next thing I know, her hand slapped me across the face, and I was thrown out of balance and fell on my ass in the middle of the dance floor. I didn’t mind being made look ridiculous if that helped Tommy, while my face started to burn – I bet her fingers were marked across it. And I thought I was going to have him to help me up, but he was already in the arms of Monika, in a long deep kiss, and I was like what the fuck, seriously, and this girl, well, woman, helped me out back to my feet.

Sam. Her name was Sam, and she was older, she told me she was 41, but a lady stops counting at 35. And she was fucking gorgeous too, curvy, a lot of meat around her bones, her tits stretching her dress in all the right ways. The first comment she said was “was she your girlfriend and just found out you were cheating on her?”

We went to get drinks, trying to have a conversation in a club is a nightmare, but I was flirty towards her, and she was flirty toward me, I thought maybe I was leading her the wrong way because I was not interested in anything serious, but we exchanged numbers anyway. We returned to the dance floor and instead of staying with her group she stayed with me, and we danced together, we kissed, we laughed, I told her “let’s just enjoy the moment,” and she told me “don’t get any feelings for me, bumblebee, it’s just sex that I want.”

Fuck. Me.

I gotta confess I was a piece of shit back then, I assumed because she was overweight, that she might have trouble with confidence, and having a guy complimenting her and flirting with her might lead to a serious thing that I didn’t want at all – as if I was Susan here – but she proved me wrong, in ways I couldn’t think of. And I’m so fucking glad she did.

My cock hardened against her leg, and she smiled, “glad to make you that happy,” and we kept dancing, I looked over at Tommy and Monika, they were enjoying themselves, and Sam taps on Monika’s shoulder, “what do you think of taking these boys to a nice motel room? I know one right down the road, women-friendly too, you’re safe with me.”

Sam knew how to live. She knew exactly what she wanted, and how to get it, and within minutes we left our own group of friends back at the disco, walked to the motel, paid for the two rooms (fucking hell!), and left the love birds to themselves.

What happens next was a new chapter in history.

As soon as the door closed, I was kissing her, but she stopped me and threw me on the bed. She, Sam, threw a 6 foot-something guy, from the army, muscular (my six-pack was missing) to the fucking bed with a strength I was only used to with my mates.

She walked towards me and straddled me. My cock was aching, but my arms reached around her, and I pulled her for another kiss, but she stopped me a second time.

“You touch me when I tell you to touch me.”

And she bent down and kissed me, we made out for an eternity, her pussy rubbing against my boner, which was in an awkward position but she didn’t allow me to adjust anything. She was having fun with my misery.

She took her boobs out of her dress and pushed my face against them, her pussy grinding against my cock, and I was getting way too worked up. Yes, I could have turned her around and fucked her brains out, but part of me enjoyed being dominated, just like I did with Susan.

She ain’t no Susan, but she was fucking hot.

Suddenly, she stood up, placed one foot in my aching cock and balls, made a comment, and took her panties off, she could wring them, they were fucking soaked. “I don’t think I got such an obedient man in a long time,” and, still standing on the bed, with me sitting on the mattress, she made me make love to her pussy. Only tongue and lips.

Damn, she was dripping.

And she was brutal too. She face-fucked me with her cunt, enjoying herself in ways I wish all women could, and she screamed so fucking loud, giving zero fucks to whoever could listen. She managed to overpower me and now I was laying flat, and she kept thrusting her pussy on my face, her strong thighs doing the job, my neck hurting, but fuck if I was going to stop, I was loving it.

Fucking loving it.

You don’t imagine the troubles I got trying to explain to women how they can treat me that way. Got a couple of them getting dressed and leaving on the spot. But damn, anything to be between your legs and be treated like a sexual object.

I was in pure bliss when she came to a halt, panting, “shit, that was the best pussy eating of my life,” she said, and then she grabbed my hand, and with open legs in front of me, explained to me how she wanted me to finger fuck her.

Finger. Fuck. Say what? I thought women didn’t like that, but she told me “I fucking love that, so you better be good, or else.”

Dude, my whole arm was numb by the time she had enough, but it was life-changing, and she taught me how to get it right on that spot, and then just keep at it, and I started to add my own personal touches, and turned out she loved some name calling, so I just nibbled her hear, licked her nipples, my skin on her neck, and then “I bet you love masturbating near other men,” and “you can’t keep your panties dry,” and also “cum for me, show me how a true slut you are,” and at this one, she tried to slap me but I saw the change in her face, I saw the orgasm washing on her, “that’s it slut, show me your true self,” and shit, she fucking swallowed my hand, I got bite marks all over myself, and my cock was leaking profusely as my fingers reached out the back of her tongue, her eyes rolling back, my brain turning to mush.

She collapsed, exhausted.

My cock was hurting. I was still fully dressed, not even my fucking shoes were off.

She grabbed me by my shirt, “you are a devil, aren’t you?” and she pushes my head down onto her pussy again, as hard as before, and man, I just went for it. At this stage, I could cum in my pants, I was never been this horny before. Never. Not even with Susan, and all I wanted was to forget about her, and Sam was doing a damn pretty good job about it.

“Thank you. You can go now.”

I looked at her, my face dripping from her cunt, she can’t be serious. I was hard for about two hours of nonstop pussy eating and making her orgasm, and she just turns to me and says I can go?

“You heard me. Go.”

Fuck damn. “Alright,” I said, thinking if I should report her for torture. “You sure?”

“Of course I’m sure. You’ve done your job. I’m tired now.”

Oh, my fucking hell!

I had a boner that could be observed from the moon. But, I picked up my stuff, and closed the door behind me, knowing that control was essential to a soldier like me. It was difficult to walk, my balls hurting so fucking much. I stopped by Tommy and Monika’s room and placed an ear against the door, and there was some wild fucking happening in there. At least I got him laid.

“Oi, the fuck you’re doing? Come back here!”

I turned around and a naked Sam is shouting at me. “You told me -”

“Are you stupid? I thought you were an army boy, not a submissive cunt!”

Gotta say, I never run this fast in my life.

My shirt lost all its buttons, she clawed my chest so damn deep, that I could see her nails marked on my pecs, I pulled her hair back as I kissed her, and this time, I showed her what being an army boy was like, no hesitations. Placebo was playing in the background, she had put the TV on a music channel, she broke the button of my shorts too, and I pressed my erection still covered in my underwear against her clit, brought my fingers to the mix, and didn’t stop until she was shivering in my arms, her mouth open, screaming oh my god, oh my god. She came so goddamn hard, and I was still at zero.

“How many times can you cum?” I had no idea about this, and yes, I heard about multiple orgasms, but it’s that sort of thing you don’t really understand, a myth, that guys tell “oh I made this woman cum fifteen times” and I was always like, “seriously? I made Susan come like one time each time we fuck, or three tops.”

“Our orgasms are different, but I gotta say, never got this good like tonight.”

“Do you want some more?” I asked, lowering my briefs, and letting my cock hit her face, and with that a flood of precum down her lips and breasts. “Because we can do this all night.”

She sucked cock better than Susan, but worse than the guys in the army, and I held my ground, not cumming from her mouth. Fucked her tits, and she handed me a rubber, never worn one before, she helped me put it on, “fucking tight,” but she complained that I should be the one having the goddamn things, and you know, point taken, and lesson learned.

I fucked her slowly at first, wanting to last, and I warned her, I can cum pretty quick, and she loved that, and did everything in the book to make me cum faster.

Less than two minutes in, she got me.

Her toes curled as I unloaded my balls, but I didn’t slow down until she told me to. “Are you going to round 2?” Yup. “Change the condom.” Why? And she rolls her eyes as if I was the dumbest piece of shit on earth.

She looked impressed as she took the condom off my cock, “guess you were needing it badly,” placed the new one on, and I fuck her for another five minutes or so, escalating the speed and how much I was giving her, and the second load came hard and fast, with her flipped on her stomach, and with me hitting her from behind. Her ass was red from my hands slapping hard on her, and she was screaming like a porno star at this point. I loved all of her.

We went for a shower, and I took a condom with me, and fuck her silly there, lasting much longer this time, we flooded the toilet, almost fell a few times, and broke the sink (well, not completely, but a chunk of it was on the floor) and ended up on the chair in the bedroom, which we broke as well, while she had her legs fully spread and all my weight was supported by the tiny frame of the wooden chair.

We ended up on the bed, with her riding me until I came.

I was in love with her body. My cock was starting to slow down, but if she wanted, I’d go another round.

But she told me she was too sore, the sun was up, flooding the room with light, and we took a nap.

When I woke up, she was gone.

I masturbated to her smell in the pillowcase and decided to take that with me as a recuerdo. I had a few texts from Tommy, and I called him. He was still in the hotel room, Monika was asleep, and they paid for another night. What a fucking stallion. And I realised the fucking mess all around me. The curtains were on the floor. The lamps were broken. I ran to the toilet, yup, that sink still cracked, shit.

It was worth it. I had to pay for another night because completely missed the checkout time, and for the damage. And they got my name on a blacklist. A fucking expensive fuck, but so worth it. I called the number she gave me, and a guy’s voice picks up.

“Hello?”

“Who’s this?”

“Is Sam there?”

And silence on the other side, deep breathing, and he said, “That girl, Sam, keeps giving this number to guys she fucks. This ain’t Sam, don’t call again. Hope she was worth it.” And hangs up.

Shit.

I went home holding my shorts together because there was no fucking button to hold them. If you ask me, I’d do everything just the same way, wrong number included. She was one of the best fucks of my life, and I got Tommy laid.

Source: reddit.com/r/gonewildstories/comments/y8wo03/how_i_got_my_best_friend_to_lose_his_virginity_mf