Note: This story works as a stand-alone piece, but probably makes more sense if you have read ‘Playing Wingwoman – By Her’
After our threesome with Chelsea Chris had been all over me for weeks. We had sex every night. We had sex in the mornings. We had sex in the bathroom at a party. We had sex in a closet at another party. We had sex in his car. We had sex in my car. I gave him head in a movie theater. We had sex in a store changing room. We had sex several times in parks. We were like rabbits.
Part of the reason we were exploring new places for sex was we were turned on all the time. Part was because Chris’ roommate, John, was sleeping in the room again. He would usually stay with Laura, his girlfriend. But right before Valentine’s Day she had broken up with him. This didn’t stop us from having sex but now we had to be quiet enough he couldn’t hear us. He and Chris both slept with music playing which made it a little easier, but there was no more bed rocking sex, and no more sex on the futon.
The beds in the room were both set up like a top bunk, but they were bolted to the wall so much more secure than a dorm bed. Chris had sheets hanging around the bed so you couldn’t see what we were doing in there. I’m sure John knew we were fucking when we got in bed but there was at least an illusion he couldn’t. Not that I thought he would care if he did. Nor did I care if he heard me at this point. There had been a few nights after drinking where Chris and I had rather loud sex while John and Laura had loud sex in the other bed. No one could see each other, but everyone could hear everything.
Chris was worried that if we were loud it would bother John. Not that John would be grossed out by us having sex, but because John was recently single. He had dated Laura since they were seniors in high school, so a little over two years. At first he hadn’t been taking the breakup well.
Chris and John were really close friends. They had been assigned as roommates freshman year and hit it off. Since becoming single John had opened up about being Jealous of Chris’ sex life at times. Not that his sex life hadn’t been good, but he wondered what it would be like to have a one night stand. He had only been with his ex. Laura wasn’t ready to settle down, and said she wanted a break to “explore herself.” John thought that was code for “sleep around” and had been moping around because of it.
“I bet she’s out going crazy,” he lamented after a few too many beers, for not the first time. “She used to want to have a threesome with Chris, before you two were together.” This wasn’t the first time he had told us this, but for some reason Chris cracked a joke that maybe they should have done it. “Would you let another guy be with Mandy like that?” John asked, more as a defense of not taking Laura up on it than as an actual question to Chris. Chris just shrugged.
“I let Chris be with another woman, in a threesome I mean.” I don’t know why I told him, but I did. “So it’s only fair if I wanted it he would do it for me too,” I added jokingly. John seemed surprised. He tried to get details out about who our threesome was with but we both said we didn’t kiss and tell like that. Then he started to go on about how lucky Chris was.
While I had been joking it made Chris start to talk about giving me a threesome with another guy. “You gave me a threesome after I made a bad joke, so I should give you one after you cracked that joke with John,” he would say. It actually did turn me on.
When spring break was coming up Chris decided he needed to get John “back out there” before we left for it. Chris wanted him to be in a mood to really enjoy himself, and was on a mission to get John laid. He felt spring break was a great way for John to get some random sex. I also think he wanted to just get John out of the room for a night. He took John out to a bar one Friday and I decided to get dinner with Chelsea and Liz.
My relationship with Chelsea was great after our night together. She wasn’t awkward about it. She wanted to do it again, which I was open to if it wasn’t for John being in the room now. I had told Liz about the threesome, and she had asked me for all the details. I asked Chelsea if she was ok with Liz knowing stuff, and she suggested the three of us get dinner and drinks together sometime. Liz had been hounding me for details for almost a month so I figured we would go ahead and all go out while Chris was hanging out with John.
“So seriously, you didn’t get jealous?” It was at least the third time Liz had asked me.
I laughed and shook my head no. “No, and I would do it again.” Liz put her hand up for a high five smiling at me. I gave her one and she said “nice”.
“But I don’t want him getting spoiled about it,” I added. “Can’t do it too often.”
Both the girls laughed. I told Liz not to tell Jessica. It’s not that I wanted to hide it from her, but I knew if she knew she would want to do it and while I wanted to try that I felt it needed to wait. escort Giving Chris threesomes with all of our friends who would do it all in the first few months of our relationship seemed a bit much.
“He had brought it up to me before,” Chelsea told us. “He had another fuckbuddy and he wanted to spend a night with both of us, so I was glad to finally do it.”
I had already heard this story from Chris. It was part of why I knew Chelsea would be ok with having a threesome with us. Liz however was very curious. “Why didn’t you do it before?” Liz asked. “With that other girl?”
“Oh, Nicole wasn’t bi. Like, at all. And she knew I was interested in trying that so she wouldn’t do it with me unless I agreed that we wouldn’t touch. I thought that was boring. Why would I share a guy’s focus if I wasn’t going to get any attention back from the other woman?” Chelsea explained. “And besides,” she leaned her head on my shoulder, “It was way more fun with Mandy.” I gave her a hug as Liz agreed that I was fun in bed.
“Chris has said he’s going to give me one, but I don’t think he’s serious.”
Both girls looked at me confused, so I clarified, “I mean give me one with another guy.”
Liz reached across the table to give me another high five and again said “nice!” Chelsea asked if I wanted to do that.
“It could be fun,” I said, “but I don’t think he’s actually going to do it. Also he made a point that he’s not interested at all in any guy on guy action, so it would only be me benefitting.”
“Well,” Chelsea said, “you and the other guy who got to fuck you.”
I thought it would be hot but I wasn’t going to press the issue with him. I figured he was just saying it hoping it would make me more likely to give him another threesome sooner rather than later. Liz meanwhile was talking about how much she would enjoy having two guys at once. She was on the other side of the booth shaking both of her fists in the air demonstrating what she would look like beating two guys off on her face at once. I tried to stop her before people noticed and Chelsea just laughed uncontrollably, which of course made people near us start to look over.
“You’re lucky, Mandy.” Liz said. “I’m going to see if I can make that deal with Mike. But he has to get me a guy first. Otherwise I’m sure he’ll chicken out.”
When we finished eating I texted Chris letting him know we were on our way back. He texted back that he was in the mood and we had the room available and said he was “getting the futon ready.” He and John had gone to a dive bar for dinner. It was still pretty early so I was surprised John had already found someone. He was an attractive guy but he wasn’t exactly smooth.
When I got to the room I found Chris sitting with John watching TV. Both were leaning back on the futon which was pulled out flat. I don’t know if I would have figured it out so fast had I not just been talking about it with Liz and Chelsea, but I immediately knew what Chris was up to.
Chris got up and came over and met me at the door. I leaned up and gave him a kiss then whispered, “You really want to do this?”
He laughed and said to John, “she’s already got us figured out.”
John looked a little sheepish, but I could tell he was giddy. He was an attractive guy. He had more of a football player build than Chris. He wasn’t tall but h wasn’t short either, about 5’9″ or 5’10”. Despite being 5 or 6 inches shorter he probably weighed about the same as Chris due to his build. I knew from seeing the guys play sports that he was fit, but he wasn’t as toned as Chris. He had a body I would describe as powerful. Seeing him shirtless made me think of a boxer. He had sandy blond hair and blue eyes. He wasn’t my normal type but when he was dating Laura I definitely thought he was the slightly more attractive half of the couple.
“Are you sure about this?” I asked John. I knew he had only slept with Laura and I didn’t want him getting emotional. He had been a lot better the past few weeks, finally seeming to get over her. He very enthusiastically nodded that he wanted to do it. I had been drinking but I wasn’t nearly as tipsy as when we had our threesome with Chelsea. I bit my lip and looked at Chris. “Ok,” I said, “let’s do this.”
Chris took me into his arms and asked I was sure I was ok with this also. I said I was then looked back at John. “Have you done anything with any women other than Laura?” I asked.
“I’ve made out with a few.” he said.
“Have you ever done more? Have you gotten a blowjob from anyone else? A handjob? Fingered a girl?” I asked.
He shook his head to say no. That wasn’t the response I had hoped for, but it would have to do.
“Here are the rules,” I told him, “I haven’t decided if I’m going to have sex with you or not yet. You may only get a blowjob tonight. If we do have sex, you wear a condom. If you cum on my face, I will punch you in the nuts. And then I will do it again every time I see you for the rest of the semester. You don’t ever tell anyone about this. As long as you are ok with that, we can do this.”
John stood up and had a tent popping up in his shorts. He tried to reposition it so it wouldn’t be so obvious. I laughed and said, “Well you may as well take it out and let me see what I’m getting. You are obviously ready.” I didn’t mean to embarrass him but he turned a little red.
Chris spoke up behind me. “We are going to give you a massage first.”
“Well you are definitely giving me a massage,” I said, liking that idea, “but not first. If this is for me were doing it how I want. So you two get naked and stand over her.” I pointed at the floor in front by the edge of the futon.
Chris and John took off all of their clothes and moved to where I told them. Chris wasn’t fully erect, but he was about halfway there. John was so excited that his cock practically sprung out of his shorts when he took them off. He wasn’t as long or as thick as Chris was, but he was above average. Right at 6 inches. His head was very thick compared to the shaft and it turned up a bit. There was a thick vein on the top of his cock that ran the entire length of the shaft. John’s entire pubic region was completely shaved which made it seem a tad bigger. I reached over and rubbed the skin right above his cock.
“Very smooth,” I said. I had seen guys shaved in porn, but somehow had seen a guy in person who had done it. Chris shaved certain places and kept the rest of his hair very neatly trimmed, which I liked. I had never considered it before, but now I was debating if I liked it shaved more than trimmed.
“Yeah, Laura always liked it like that, so I have just kept it up.” I looked up at him and saw he wasn’t getting emotional talking about Laura. The last reservations I had went away. He was ready for this. I sat down on the futon, leaned forward and swallowed his entire cock. No teasing or prep work. I opened my mouth and took him down my throat until my nose was pressed against his smooth skin and his balls were on my chin.
“Holy shit!” John exclaimed.
I heard Chris start to laugh and say something like, “I told you.”
His bulbous head strained in my throat as I felt his cock twitch. I moved my tongue in little circles on his shaft in my mouth, and gently rubbed my fingers on his balls. I pulled his cock out and took in a breath. “I approve of you being shaved,” I said. I wasn’t lying, it was pretty nice. “Chris, I want you to shave like this for me too.”
“You mean right now?”
“No, dumbass,” I laughed, “but soon. That ok?”
Chris rubbed his hand on his chin like he was contemplating. “I don’t know, letting you fuck my roommate is one thing, but me shaving completely. That’s a lot to ask a guy.” I grabbed one of the pillows and smacked him. I knew he was going to shave for me now that I had asked.
“Tell me how this feels,” I said. I started licking the smooth, shaven skin above John’s cock.
“That feels fucking amazing.”
“Ok,” Chris said, “you’ve convinced me. I’ll do it.”
I winked at him and said “I know you will.” I reached over and grabbed Chris’ cock. He already kept his balls shaved for me, so I took one into my mouth and sucked on it. I stuck my face under him and licked on his perineum. He also already kept that shaved at my request. Basically anywhere my mouth and tongue were going, I wanted bare.
I grabbed both of the guys by the waist and pulled them closer to me. I took turns sucking Chris’ cock then John’s. Chris got very hard very quickly. I probably could have made them both cum in a few minutes, but this wasn’t for them, it was for me.
“I’m ready for that massage,” I told them.
Rather than have them try to undress me while I was laying on my stomach I stood up and took off my t-shirt and jeans. I laid down on the bed wearing just a bra and a thong. It wasn’t my sexy lingerie, but it was cute stuff I had bought at Victoria’s Secret.
Chris got on the end of the futon near my head and John moved down by my feet. Both of them started rubbing on me and giving me my massage. John had pretty strong hands and was working my feet and calves while Chris was running his fingers through my hair massaging my scalp and then moving down to my shoulders.
Having four hands rub all over me like this was intoxicating. I loved being the center of attention. The fact that both guys were naked and their stiff dicks would occasionally brush against me made it even sexier.
Chris unclasped my bra and slid the straps off my shoulders. John took this as a cue and slipped my thong down my legs. It was the first time I had been naked in front of a new guy since my first night with Chris. I spread my legs apart a bit and looked over my shoulder. John was fixated, staring at my pussy.
Chris’ cock was near my face so I started to suck on it. I wasn’t blowing him in a way to make him cum. I was just enjoying myself. Gently sucking the tip, licking on his shaft, gently rubbing his balls with my hand. Both of his hands were rubbing my back the entire time I tasted him.
John was rubbing my thighs and my ass, but he had also started gently kissing the back of my legs. When his face moved up and his lips finally touched my ass cheek I put my hand on his head and gently pushed him toward my pussy. That was all the encouragement he needed. His tongue started to lick up and down my lips and he immediately slipped a finger into my wet slit.
John playing with my pussy felt good, but he wasn’t going to be able to get off in the position we were in. I rolled over onto my back, exposing my naked front to my boyfriend and his roommate.
“Wow,” John said when he first saw my tits. I rubbed them and them squeezed them together and asked if he liked them. “Oh my God yes,” John said.
“Well get down there and make me cum and I’ll let you play with them,” I told him.
John dutifully obeyed. He grabbed my thighs and held them apart. His face moved down between my legs and I felt his hot breath against my pussy. He slid his fingers back into me and started to spin his tongue in small circles over my clit. He was quite good, Laura must have taught him well.
Chris leaned down to kiss me. I moaned into his mouth. I loved feeling his tongue pressed against mine while John’s tongue was pressed against my clit. John’s hands were rubbing my hips and thighs while Chris was rubbing my shoulders and squeezing my tits.
It took no time for the guys to bring me to my first orgasm. I was so turned on by having both of them to myself at the same time. I clenched my legs around John as it came over me. It wasn’t a particularly intense orgasm but it seemed to last forever. Chris sat up and was holding my head, rubbing on my neck and shoulders. John was holding my hips steady and he kept licking my pussy throughout my orgasm.
When my orgasm finished I pushed John away from my pussy to give it a rest. Chris slid around to lay next to me and started to kiss on my fight breast. John slid up next to me and grabbed my left one. I laid on my back basking in the glow from my orgasm while feeling both of my nipples being sucked at the same time. All four of the guys’ hands were rubbing all over me.
I was rubbing my fingers through Chris’ hair, while rubbing on John’s head at the same time. John’s hair was very short, whereas Chris had long shaggy hair that I could play with.
Both of the guys were still rock hard, and I noticed John kept reaching down and stroking himself. I knew he wanted me to suck him off, and he wanted even more for me to spread my legs and tell him to put it in me.
“Stand here John,” I told him while pointing to where he had been standing when I blew him a few minutes earlier. I made Chris lay on his back so his ass was near the edge of the futon and his feet were on the floor.
I straddled my boyfriend reverse cowgirl style and slowly lowered myself onto him, taking his shaft into me. He was incredibly stiff, and he felt really good getting deep into me in this position. I rocked myself back and forth on his cock while he was rubbing my ass and holding my hips.
John’s was standing in front of me. His cock pointed toward me while he held it in his hand. He was still slowly stroking himself. It was a nice looking cock. I reached out and wrapped my hand around it. I gently pulled on it and he stepped toward me. I leaned forward and took him into my mouth.
Riding a guy and blowing another takes some coordination. If you can’t rub your stomach and pat your head at the same time, you probably can’t do this either. At first I had to concentrate, but after about 30 seconds I got into a rhythm and started to enjoy myself.
Chris was holding my sides and I had one hand on John’s side while I was using my other in unison with my mouth to pleasure him. I tasted a bit of pre-cum in my mouth and decided to slow down on trying to make him cum. I took my hand off his dick and started to rub my pussy.
I was incredibly turned on and I had already came once. I knew it wouldn’t take me long to get off again. Chris felt so big inside of me. His cock was filling me up while John filled my mouth. John was holding my head, running his fingers through my hair while I used my lips and tongue to bring him closer to orgasm.
I was getting incredibly close myself. I decided to focus on making myself cum rather than getting John off. If he outlasted me I thought I might even let him fuck me.
Chris must have realized from my moans that I was getting close because he started thrusting into me a little more forcefully. He was gripping my hips and fucking me harder and harder. It became too much for me and John’s cock fell out of my mouth and my head fell forward.
This orgasm was more intense than my first one. John held my shoulders while my body twitched and trembled. Wave after wave of pleasure hit me while John and Chris tried to hold my body steady. I let out a loud moan of pleasure as my orgasm finally ended.
Chris leaned forward and wrapped his arms around me. He slowly leaned me back and laid me down on the futon.