I teach a virgin how to have sex before taking his virginity [F]

When I was 18, I was going through one of the harder breakups I have had. I spent a lot of time with a good guy friend of mine that had told me he was interested in me, but I had two reasons for being leery about starting a relationship with him. First, I was still pretty hung up about my breakup with my ex. I did not want to continue the relationship and I knew it had run its course; I just was hurting still. The second part was that he was a virgin and he had told me he was worried about not being “good enough” and I was worried that would create an issue with us.

So, I asked him if he would like to “learn” what to do just as friends. He agreed and several times a week, I would go to his house and show him what to do with me in an escalating fashion. We started simple and worked our way up to doing everything except sex itself. It was simple in the beginning with just kissing and light touching, and we worked our way up to oral sex. I don’t know that it was necessary to show him what he needed to do when I gave him blow jobs, but it seemed like the thing to do at the time.

The Week of Sex That My Roommate Won From Me in a Bet… Part 2 [FM]

I really hate losing anything. Especially bets.

(This is the second part of the week and the third part of the overall story. Those can be found in earlier posts.)

It had been maybe 6 hours since we had arrived at the cabin. I had found some shorts and a tank top to wear. Turns out some of the clothes he brought were mine, just the ones he thought were something that looked good on.

We had dinner before going to sit in the small living room area. There was a TV with no cable, just the selection of movies they had on the shelf next to the small TV.

He picked something and put it on. I was sitting on the single armchair while he went to sit down on the long couch. He patted the area next to him. I made a decision that moment. I could pout all weekend, mad because I lost the bet. Or I could have a fun week with someone that I may not like personally but I really enjoy having sex with. I have had worse offers.

Starved for sex, hot stranger bangs me in the bathroom at work [F]

Sometimes you just want to get fucked…. you know?

After a dry couple of weeks, I had become sexually frustrated to the point where I was starting to consider going through my phone and asking guy friends to do me a favor. My roommate at the time decided she was fed up when I offered to have a threesome with her boyfriend and her.

“Just, chill out, okay?” she yelled at me, “You will be fine!”

I did not feel fine, but I decided to pick up extra shifts at work to focus on something else. I lived in a town that was mostly centered around the university I went to. I worked at a small restaurant that was away from the downtown area, closer to where the people that actually lived in the town were.

It was a busy night, and my boss had decided we only needed two servers there when a third girl had called off her shift. When I walked in, I saw the relief on my coworker’s face, she looked like she was seriously overwhelmed. I looked around; we were super busy again tonight.

The week I lost to my roommate… part one [F]

This is the continuation of this story: https://www.reddit.com/r/gonewildstories/comments/muuqa2/my_bet_with_a_roommate_i_lost_f/?utm_source=share&utm_medium=ios_app&utm_name=iossmf
So it makes more sense in context. This is part one of that week…

It took Jake maybe 6 weeks to set up the week he won from me. As much fun as our house was… I think he thought it would be better if we were away somewhere. He let me know when we were set for our week arrangement by leaving me a note on my door. You know, so all our roommates saw it too.

He had arranged for us to go to his family cabin, a two-hour drive north of where we lived. I guess he really wanted to make it count. I had seen him go there a ton of times and I was always curious. I had a few things to get my things in order.

Lex helped me pack. She made quite a few nasty suggestions to help me get out of the entire week. I just nodded along as she suggested a range from knocking him out to just going back on the entire thing. She was not super thrilled that she would be on her own for the whole week.

Rough sex makes a work trip one for pleasure [F]

One weekend I had to go to another city for a work thing. They put me up in a nice hotel that was more of a suite. The second night there, I invited a guy over that I had met at the work thing that I had done that day. He seemed nice and besides he was gorgeous. I took my time getting ready and was finishing my makeup when he arrived.

I heard a knock on my door, and I took my time answering it… best not to look too interested. Opening the door, I noticed he had some takeout in his hands. He told me he thought it was easier than trying to cook or find somewhere to go… Looks like he is just as excited to see where this goes as I. We ate in silence for a few moments, a few comments and questions were asked before we fell into silence again. After a few minutes, he spilled something on the front of his pants. I told him to strip out of them and that I would send them down to be washed. I went and put the pants in the laundry before stopping into the bedroom to grab a pair of sweats that I thought he would be likely to fit into. Before I made it back to the couch area where I had left him, I went into the bathroom to grab something to clean up the mess that was not spilled on his pants. I bent down to get something out of the cabinet and when I straightened, I saw him standing at the door of the bathroom.

When 30 miles feels like forever… [F] One of my neighbor stories

When you live in the middle of nowhere, you drive A LOT. Trips to get necessities or whatever you need take hours instead of a couple of minutes round trip driving. Depending on what store I need, I must plan around the time it takes to drive into my shopping trip. Because of this, I often take people with me, like my neighbors or friends, when I need to make a trip. Then it saves them the gas and I have someone to talk to.

Someone I go with the most often is one of my guy neighbors. He likes to drive so I can

just do whatever as he drives. A few weeks ago, we got hung up way longer than we were supposed to be when we drove to a town two hours away. We had a lot of things to get, including some things for his mother, and we ended up coming back late at night. About an hour away from home, we started talking about our sexual experiences and what some of the best stories were. He told me about this girl that had given him the “best blowjob ever” in a movie theater once. I checked the mile marker to see how far we were from getting back, 30 miles out, so I decided to make the ride more interesting.

My bet with a roommate… I lost [F]

There is something compelling about angry sex. To legitimately be angry with someone and to take it out in the form of sex is an intoxicating feeling.
During my time in the city, I lived with a lot of people. We lived in a large place with 8-10 roommates at a time. With that many people it is inevitable that you’ll step on some toes now and then. I had a particular problem with the guy that shared a wall with me. He would bring different people home all the time and he definitely had some interesting kinks. I didn’t mind either of those things. What I did mind was that every time I had to be up really early it seemed that it would be the night that I was kept up until 5 in the morning with the screaming and loud bangs from his room. I tried talking about it, but he would write me off as being jealous. That made me incredibly frustrated. So, we would get into some pretty epic yelling matches.
One night, I had a meeting I had to be at 8 am. It was a really important meeting to me, and I wanted to look my best and be on the top of my game. I had not even bothered to say anything to Jake, my next door roommate, because I knew it was more likely that he would try harder to find someone to torment me with that night.
It ended up not mattering. Around 1:30 a.m. I woke from a dead sleep to hear that Jake had indeed brought someone. The banging and moans started up, but for some reason they stopped suddenly, and I heard arguing voices. Suddenly, I heard the door to Jake’s room slam, and someone stormed down the hallway towards the front door. A few moments later the front door also slams, and I hear the catcalls and jeers coming from some of our other roommates.
I had two choices then; I could ignore the whole thing and go to bed, that way I could get some sleep and do my best tomorrow. OR I could go over to Jake’s room and see if everything was okay… The second option did not seem like something I wanted to do at all but for whatever reason, I felt like I had to go check in on him.
I knocked lightly at his door before pushing it open. It had been slightly ajar which makes me think that he went after whoever it was that rushed out of here a moment ago.
“Hey,” I said, taking a step into his room. He was sitting back against his pillows, looking up at the ceiling. “Everything alright?”
He sighed, “Yeah she was just being mean,” he told me as his eyes tracked to me. “Are you lost?
I frowned at him and shook my head. “I came in to check on you.”
He looked legitimately surprised. “Wow, that’s surprising.”
I turned and went to leave but he chased after me, “Wait, that is so nice of you. Come sit with me a minute.”
We sat down, side by side on his bed, our conversation felt stunted, like we were not sure what to say to each other. After a few minutes, I said my good nights and I started to stand.
“Wait,” he said catching my wrist, “unless you’d like to take that other girl’s place for the night…”
I laughed, “I don’t think you’re exactly my cup of tea.”
“I bet I am, in fact I bet you would really enjoy it,” he told me.
“I bet I wouldn’t even get off,”
“I will take that bet,” he told me, shaking my hand. “What do you get if I win.”
I was stunned silent for a moment. He wanted to make a bet that he could get me off?! I did not immediately shoot down the offer, which surprised even me. It had been a bit of a dry spell and he was smoking hot. At the very least I would have a good time and it may even help with my meeting in the morning. And I could possibly get something I wanted in return…
“Deal.” I shook his hand. If I win, you cannot bring girls into your room for a month. You have to go somewhere else to be loud.”
He shook his head before answering, “Fine. But if I win, I get to fuck you whenever I want, wherever I want, however I want, for a week. And I get to pick the week at a later date to cash in.”
“I don’t think that’s quite fair…,” I started.
“A month is much longer than a week, Maddy. Plus, my win will be fun for both of us. Your win will only be for you,” he said with a wicked smile.
“Deal.”
I went to shake his hand again but instead he grabbed it and flipped me around, pulling my back against his front. I could feel the stiffness in his pants against my butt as he ground into me. He pushed my hair aside and put his mouth to my neck. “I’m going to make you scream,” he whispered. I felt my panties grow damp.
He used his hold on me as leverage to force me onto my knees on the bed. He ran his hands over the thin fabric of my pajama pants that covered my ass. He stroked me a few times this way before slapping my ass… hard. I cried out but before the sound even finished leaving my lips, my pants were on the floor.
“Maddy, you don’t wear underwear?” he questioned, taking his fingers to trace the opening of my pussy.
“Not to sleep,” I told him.
“That might have been a mistake,” he said before grabbing me by the hips and flipping me onto my back. He was rough. He pinned my arms above my head and leaned in like he was going to kiss me. I moved to accept the kiss but instead he plunged his fingers into me and thrust them over and over in and out. I bit down on my lip to keep from crying out.
“Come on Maddy, I know you’re feeling good… you don’t have to be quiet…” He flipped me onto my belly and continued his finger assault on my small pussy. I groaned into the pillows.
Jake readjusted so his arm wrapped around my front where his hand found my clit. He started working me there, fast and hard. I moaned and he reached up and took a handful of my hair. He tightened his fingers into a fist, pulling my head back with my hair. “I told you I want you to scream for me.”
I whimpered, it hurt that he had a hold of my hair, but I also felt a rush of wet between my legs as his rough voice told me what he wanted me to do.
He used my hair to force me up on my knees in front of him and pushed me up against the wall. My boobs were smashed into the cold of the wall as his mouth worked up and down my neck, his hand never relinquishing the grip in my hair.
After a minute he pulled my head back again hard, the pain making me cry out. He pushed me onto my back, his hands going to my shirt. He pulled it off in a fluid motion and pulled the fabric of my bra down to my belly, exposing my nipples and breasts. He took one fully in his mouth, sucking and scraping the nipple with his teeth. It was simultaneously pleasure and pain. With his other hand, he plugged two fingers inside of me again. I cried out as I came onto his hand, my juices soaking into his hand.
“Oh Maddy…. We’re going to have so much fun… for a whole week.”
I started to say something, but he shook his head. He pulled my legs to either side of him and positioned himself at the entrance of my pussy. He slid in in one fluid motion, filling me, and my mind went blank. I wrapped my legs around his waist, urging him to go deeper and harder. He wrapped his arms around my back and lifted me up. Holding me up in the air he thrust into me over and over. He slammed me into the wall, my back hitting against it as he continued to drill his dick into me. Over and over, he continued for what seemed like hours. Every time I started to go over the edge with an orgasm, he would slam us up against the wall, the pleasure mixing with the pain.
As I neared the edge of yet another orgasm, my pussy clamping down on his hardness, I felt him swell inside of me, the added size sending me over the edge as he finished with me. My back slammed into the wall with each of his final thrusts, I felt dizzy with the pleasure of it all.
As he pulled out of me, I slowly slid down the wall, my head spinning.
“So, I guess I will just let you know when that week starts then?” he told me with a wicked grin,
I nodded, still dazed by the entire thing. As my senses began to return to me slowly… I realized that a week wouldn’t be such a difficult thing to lose in the bet… I would be really sore though if tonight was any indication.