The wingman awap

Right out of college, I was single and just starting out. I was in a semi-serious relationship with a guy at the time, meaning we had been together for a few months at that time. We spent a few nights a week at each other’s apartments, spent most weekends together, but had not met each other’s families yet or anything like that.

My roommate Jen came home one evening and asked if I had plans the following night. I didn’t have anything set yet and told her that, and she told me that this guy she had been after for quite awhile finally agreed to go out with her. The only problem was that she needed to find a date for his friend for him to agree to go out with her. So she asked if I could PLEASE do her this favor.

I hesitated because I obviously had a boyfriend that she knew about, and had met several times, plus, who seriously wants to get set up with the ugly friend (my assumption at the time anyway). After Jen promised to do all the cleaning in the apartment for the next month as well as cover all the utility bills the next month, I agreed. Besides, I knew how much she wanted to go out with this guy.

I did make up a little lie to my boyfriend and told him that Jen and I were going to have a girls night, something we did every couple weeks anyway,and just left out the part about the guys. I wasn’t too concerned as I figured I was getting the ugly guy anyway.

When the guys arrived, Jen’s date Luis, introduced us to his friend Stephen. I was shocked, I had met Luis before and he was a very good looking guy, but Stephen was gorgeous. 6’2″, sandy brown hair, green eyes, chiseled jawline, and even through his sweater you could tell he had an athletic build. Luis laughed, “yeah, he gets that reaction all the time.” I introduced myself and we left for dinner.

The restaurant we were going to was only a couple blocks away, so we walked instead of driving and I took advantage of the cool air to take hold of Stephen’s arm for warmth. He put a hand on mine to help keep me warm, and we walked like that to dinner.

Throughout dinner, the conversation flowed easily, both guys were amazing to talk to, shared about themselves but kept the focus on us. I did my best to play wing-woman for Jen but kept getting distracted by my date. I didn’t even notice my text messages blowing up as my boyfriend was trying to chat with me.

A glass of wine with dinner turned into two more after dinner, and a martini at the bar next door. I knew I was drunk, but not to the point of losing control or anything. As I went up to the bar to order one more round of drinks, I felt a body press against me from behind and a strong hand grab my ass. I didn’t have to look to see who it was as the smell of Stephen’s cologne hit me. I melted back into his grasp as his free hand took my chin and turned my face towards him, bringing our lips together. The kiss lasted until the bartender cleared his throat to get my attention. Stephen looked at him, ordered three shots for all four of us, then laid his credit card down.

When we sat back down at the table, Stephen’s hand went immediately to my thigh, while my foot ran up and down his leg. We each did our shots and got up to leave.

As we got to the front of our apartment building, Jen mentioned that the guys should come up and hang out for a little while, which they agreed would be fun.

We got upstairs and as soon as we were in the door, Luis took Jen to the love seat while Stephen and I fell on the couch, in a deep kiss, his hands sliding up the front of my body. He hooked his fingers inside my dress straps and pulled them down my shoulders, bringing the top of my dress down to my stomach. He started kissing down my neck and upper chest, stopping only long enough to unhook the strapless bra I was wearing and toss it aside, freeing my breasts. My arms were wrapped around his neck as he paused to stare at me, then brought his lips back to my chest, going first to my left breast, then my right.

I looked over and Jen was on her knees in front of Luis, who was on the love seat, pants and underwear around his ankles. Her head was bobbing, clearly sucking his dick. I slid my dress down and off, leaving me in justly panties, as he pulled his shirt off. I sat him down and pulled his pants and underwear off. His dick was a very nice 7 or so inches as I took it in my hand. I lowered my head,and took the semi hard cock deep into my mouth.

I love the feeling of a soft dick in my mouth that gets hard as I suck it. It didn’t take him long before he was hard and I could taste the pre-cum dripping. He started to tense up and pulled my head off of his dick, flipping me onto my back on the couch. He pulled my panties off and buried his face in my pussy. I took a quick peak over, and Jen was still working Luis’ cock and he looked over and smiled at me, with Stephen licking my clit and reaching up squeezing my breast.

After a couple minutes, I couldn’t hold it, and orgasmed hard, squeezing his head between my thighs.

After my orgasm, I stood up and took Stephen’s hand, leading him to the love seat, where he sat next to Luis. I straddled Stephen, and slid down his cock as Jen followed my lead and did the same to Luis, both fucking our guy while we were right next to each other on the love seat. I hung my breasts in Stephen’s face so he could suck my nipples, before sitting straight back up.

Luis reached over, and squeezed one of my breasts, which pulled me slightly closer to Jen. She leaned in and whispered in my ear, asking if I wanted to switch. I just smiled and nodded yes.

We stood up,and as we were switching, she grabbed me by the waist and kissed me, pressing her body against mine. The guys stared, wide eyed. The kiss lasted maybe five seconds, before we separated. I looked at Luis and saw why she wanted to switch. While Stephen had a nice 7-8 inch cock, Luis was much smaller.

I still sat down on Luis’ cock, letting him slide in as I leaned in and kissed him. About the same time I heard Jen gasp,and I knew Stephen entered her. I actually got a little jealous. Luis moved well under me, but I definitely wasn’t getting the same satisfaction out of him. As I felt him tense up to cum, I reached down and started rubbing my clit, coming to my second orgasm as he came in my pussy. Stephen and Jen both came shortly after.

Luis and I moved to the big couch and Jen and Stephen joined us so we could all sit together. While the guys were recovering, Stephen was between us and had each hand on our pussies, lightly playing with us. I was between both guys, so I played with both dicks to help them along.

After a little while, the guys were ready for round two, and Stephen laid me on my back. We had what would be considered more passionate sex versus the fucking that had gone on earlier. Jen and Luis went back to her room and I assume did the same. Stephen and I both came again there on the couch before going back to my room and going to sleep.

I woke up in the morning to knocking on our apartment door. I could already tell I was hungover. I couldn’t find any clothes so just grabbed a blanket and wrapped up somewhat. I opened the door, and my boyfriend was standing there. He asked why the hell I didn’t answer any texts or anything. He had been texting and calling all night. I started stammering some excuse as he looked me over. My hair and makeup were a mess, the blanket fell off my shoulder exposing one of my breasts, and couch cushions messed up behind me.

I apologized and told him I needed to go shower and would call him after. I gave him a kiss on the cheek and as I was closing the door, Stephen walked out of my room naked to cross the hall to the bathroom. I went in after him and pulled him into the shower for one more round before getting back to real life.

I somehow convinced my boyfriend nothing happened but we didn’t last long after that. Luis and Jen ended up getting together and dating for a couple years. I tried seeing Stephen a couple more times and while the sex was really good, he wasn’t ready to be tied down.