Playing Wingwoman - by Her

Spring semester was starting and I had been back on campus for about a week. Chris and I had been dating ever since the Halloween party. Things were about as serious as they could be for two 19 year olds who had known each other for about three months.

I had really opened up about sex since we started dating. With my previous two boyfriends, sex never really seemed to click. It felt awkward or uncomfortable. With Chris it was amazing, very natural feeling. It was also almost a daily occurrence. Sometimes it was a several times a day occurrence.

Being home for Christmas break had been excruciating. When you are used to getting laid literally every night, going a month without so much as a kiss sucks. My parents also tend to snoop so I couldn't take any of my sex toys home with me.

My mom did corner me for "the talk" when she found out I had a new boyfriend. She told me to be safe. I tried to tell her that I was waiting for stuff like that but she didn't buy it for a second. It was awkward, but on the positive side I finally started on birth control. When I told Chris about it he said we should both get tested so we wouldn't have to use condoms anymore. At first we still used them most of the time, to be safe, just not all of the time.

Getting back on campus was great. Classes started on a Monday and I had come back the Friday before. That gave me a full weekend with Chris with no responsibilities. We still had to use condoms that weekend. My doctor had told me I had to take a week of my birth control before it would start working. We waited two weeks to ditch the condoms just to be extra careful.

Chris told me he had done it before with a friend-with-benefits who was on the pill who had been tested, so it wasn't a first for him. He did tell me he had never cum inside a woman before though. I didn't realize how much I would like feeling him cum inside of me. Not that it was any kind of intense physical pleasure, but it was satisfying feeling his hot cum shoot inside of me.

Liz was still dating Chris' fraternity brother, Mike. Mike wasn't quite as tall as Chris, but was a similar build. They were both lean and very fit. Mike was about 6'0 and Chris was 6'3". Liz really liked him. She and I spent most nights at the fraternity house now. Liz's big, Carrie, also spent most nights with her boyfriend there.

Of the 40 or so guys who lived there about 15 had girlfriends there most nights. There were also a handful of single girls who always seemed to be hanging out there. Most of the girls who hung out there were really cool. There were also another 7 or 8 guys who always stayed at their girlfriends place. Lucky for me Chris' roommate John was one of them, so we almost always had the room to ourselves.

Since I was dating Chris the sex with Jessica had stopped. It's not that we fooled around every night before, but we had done it 4or 5 times in the first 3 months of the school year. She wasn't seeing anyone, but she had another random hookup since the Halloween party. She loved to make fun of how Liz and I had both drunkenly met our boyfriends at the same party. She also loved to joke on Liz for getting a facial her first night even though it was the type of thing Jessica would do too.

Liz's only complaint about her relationship was that Mike expected facials almost every time they had sex and she didn't know how to say no to it.

"We're getting good at it," she told me once. "If careers in finance don't work out for either of us, we can do homemade porn. I don't even have to close my eyes anymore because his aim has gotten that good."

"How often does he give you one?" I asked.

She shrugged and said "three of four times a week, sometimes more."

I had never gotten a facial. Chris wanted to do it, but he didn't pressure me about it. I didn't find it degrading or anything like that, but had heard enough horror stories about friends getting it in their eyes that I hadn't let him do it yet. The closest we came would be that he would pull out and put the tip of his cock in my mouth so I could swallow his load. We both really enjoyed that.

Chris and I had traded all the full details of our sex lives. It turns out his friend Chelsea, had in fact been a friend with benefits. She was also the only person he had fucked without a condom. And when I say they had been fuckbuddies, I don't mean once or twice, but at least once a week when they we're both single, which had been most of their freshman year.

I was surprisingly ok with Chris being such good friends with someone he had slept with. To be fair, Liz and Jessica were two of my best friends, and I had spelt with both of them. Chris knew about my lesbian experiences but he kept it a secret from the girls that he knew. He also said he didn't mind me exploring my bi side with them every now and then, as long as I gave him details. So far I hadn't been willing to take him up on that offer.

While I didn't think Jessica or Liz would want to talk with Chris about our experiences Chelsea preferred to have everything in the open. She was more than willing to tell me anything I wanted to know about her past sex experiences with my boyfriend. She and I actually had started to become pretty good friends. She was pretty cool, and had a similar course of study to mine. I wasn't worried about her ever trying to steal Chris. They wanted completely different things out of life and would never have worked as a couple.

While I had more oral sex partners than Chris, he beat me for full-on sex. Even if I included my four women that only put me at seven people. I was the tenth woman Chris has slept with. Several of his girls had been long term girlfriends which meant when counting the number of times it was well over 100 before we met. I liked that he was open with me about his numbers, and I liked that I could be open with him about mine without worrying about him judging them.

Discussing all my past exploits made me realize just how crazy I had been the past year and a half. Liz and I had made out at countless parties. I had won a wet T-shirt contest on spring break freshman year. I let lots of people do body shots off of me on spring break too. I had flashed for beads then as well. To someone who didn't know me I probably came off as a total slut. Honestly, other than not spreading my legs with a lot of guys I was a bit of one. Including Chris I had then blown 32 guys, fucked three, and had sex with four women. Chris didn't judge any of that. In fact most of it turned him on. I still wanted to do wild stuff, just now I wanted it to be with Chris.

It was Saturday and we were supposed to have lunch with Liz and Mike. Mike's roommate had gone golfing though, leaving the room to Mike for a few hours, so Liz texted me that they were bailing to have sex. In college when you have roommates you take any opportunity you can get. So instead Chelsea came with us. Thanks to a drinking game Chelsea had recently learned that I was bisexual and had seemed really interested in that fact. As soon as Chris went to the bathroom she brought it up.

"So, let's say, I wanted to pick up a woman, where would I go to meet women who are into it?" She asked me.

I laughed. "There is at least one gay bar in town, but I haven't been to it," I told her.

Chris returned to the table. "What are you two talking about?"

"Your girlfriend is going to take me to a lesbian bar." I gave Chelsea a surprised look as she said it. "What? You're bi and experienced. I'm pretty sure I'm bi with no experience. I want someone familiar to go with me."

"Did you know she was bi-curious?" I asked Chris.

He nodded while taking a sip of his drink. "Yeah, she has talked about wanting to hook up with a woman forever." Chris smiled. "You know, maybe you would be more comfortable your first time if a guy was involved. Like a threesome. Say, with your best friend who you have already slept with and his experienced bisexual girlfriend who you have already said is incredibly sexy. If that couple hypothetically existed."

"Don't push your luck," I said.

The idea of a threesome did turn me on. But I figure some spontaneity needed to be involved if we did it, and likely also some alcohol. It wasn't something we were going to do sober after lunch. And if I we're going to do it, while Chelsea would be a lot of fun Jessica would be my top choice. Liz would be second if she were single, but since she wasn't Chelsea would be next. That said, Chelsea had an amazing body, and I was a little curious about it. I also had never felt fake breasts, and Chelsea had quite the pair.

"Alright," Chris quickly gave up on the threesome idea. I knew he was only half-serious. "But you two should check out a lesbian bar. You've both talked about wanting to go to one. Why not go together?" It wasn't that ridiculous of an idea, so we decided to do it. The next weekend we decided to find one.

I didn't know of any lesbian only bars near us, but there were several gay bars I knew of and wanted to visit in a nearby city. The one I really wanted to visit was a high end cocktail bar, but you had to be 21 to enter and from what I heard our fake ID's wouldn't pass there, so that one was out. It was also an hour drive at least. There was one gay bar in the town we were in school in. It was "18 to dance 21 to drink" so we went to that one.

We went on a Friday and it was quite the experience. We didn't know it until we arrived, but there was a drag show that night. It was a ton of fun, but not something we expected. There were also a lot of straight people there because of the show. We grabbed two seats at a high top table not far from the dance floor. After a drink and a shot Chelsea got up the nerve to hit on a woman she thought was hot. Unfortunately the woman was straight and just there for the drag show.

While Chelsea was up a couple had come over to me and started flirting. Both of the girls were in college and both were very attractive. One was a brunette, the other was dirty blonde. They were both average height, thin, pretty faces, probably B cup breasts. Both women I would have slept with had I been single. They asked if "my girlfriend" and I would want to join them for drinks at their place. My first trip to a gay bar and I was being hit on by lesbian swingers, it was amazing.

I explained to them that Chelsea wasn't my girlfriend, but I also wasn't single, and was only here playing wing-woman for my friend. They asked if I was experienced with women and when I told them I was they joked that it was unfortunate that I wasn't available for fun later. I very briefly considered Chris' offer for me to play with women as long as I gave him the details, but I couldn't abandon Chelsea before she had met someone. Had Chelsea not been with me I probably would have left with them and this would be a wildly different story.

We chatted for a while when Chelsea came back, and they flirted with her for a while, but they didn't seem to be big on the idea of picking up a woman who was new to women. When they left our table Chelsea also told me that a threesome was too much for her right now.

"I mean, I've never even really kissed a woman yet, so to go home with a couple, that's just... that's more than I can handle as a first experience."

"Wait, you've never made out with a woman?" I asked. She shook her head no while sipping on her drink. Chelsea had been pretty adamant that she had feelings for women, so I was surprised she had never even kissed a woman. I mean, I knew straight women who made out with other women all the time, so a bi-curious woman had to have had plenty of opportunities for it.

We both had two cocktails and a shot each at this point, and were a little tipsy. Chelsea looked incredibly sexy. She asked me what to wear, and I told her to wear the same kind of stuff she would to attract guys. I also told her to cut her nails, which she hadn't been happy about but had done. She was wearing a pair of dark blue jeans with a low cut black top with no bra. I kept having to force myself not to stare at her cleavage. Her breasts may have been fake, but that didn't mean that they didn't looked amazing. I wanted to drag her to a corner, slide her shirt wider open and just go to town playing with them.

"Chelsea, we are getting you laid tonight." I made my declaration, I would find Chelsea a woman. "You are fucking hot, and I need to find you someone before I jump you and make Chris mad at me." I made the assumption that his offer to hook up with women didn't extend to his best friend.

She laughed, "I don't know," she said. "I want to do it, but I'm really nervous. What if I'm not good at it?"

"Well, are you good at sex with guys?" I asked.

"I think so. I mean, I've never fucked a guy who didn't think it was good enough to want to do it a few more times." After answering she then looked like she was curious about something. I had to press what it was before she asked, "Has Chris ever given you any details of our sex life?"

"Just that you two did it a lot, and that you were on the pill, so until I went on it you were the only woman he had fucked without a condom. But he also said he never came inside of you." She nodded that all of that was true. Then one detail I wanted to know did pop into my head. "Did he ever give you a facial?" I asked, a little more bluntly than I meant to.

Chelsea almost choked on her drink and giggled a bit when I asked. "Yes. Yes he did. Why?" she asked still giggling.

I told her about my conversations about facials with Liz, and said I knew Chris wanted to do it, but I was worried I may not like it and so far everything with him had been perfect.

"Well, if it makes you worry less, Chris has cum on my face at least a dozen times, and he only once got it in my eyes and it wasn't as bad as I thought it would be. But I did look like I had pink eye the rest of the day."

We talked a little more about her and Chris. She said most of their sex had been almost business like. They would get together, get her off, get him off, then get dressed and be done. Once or twice they had all night sex sessions, but it wasn't the norm for them. She said she rarely spent the night, usually leaving after they finished. Always the gentleman he would always walk her home. They had always used condoms, except the last few times they did it after both getting tested.

She suddenly gave me a pensive look, "Can I ask you a question?" before I answered that one she asked another. "Do you two do it doggy style?"

"Yeah, all the time."

"When you do it does he put his thumb in your ass?"

I couldn't help but laugh as I said no.

"He always did that to me," she said. "I actually liked it."

"Did he ever put anything else, like, anything bigger perhaps, in your ass?" The topic of anal sex hadn't come up. I didn't know if Chris had ever done it or not.

She shook her head no. "I think I'm going to reserve that one for a boyfriend, not just a friend." She took another sip of her drink before adding, "or at least try it with someone with a smaller cock my first time," which made me laugh some more.

Surprisingly I was actually getting turned on thinking about the two of them together. I didn't want to get too worked up, so I decided to shift the focus of the conversation back to her.

"So what do you want to do tonight?"

"I don't know," she said. "I haven't been laid in months. I kind of want a random hookup, but I want my first time with a woman to be really good too. I'm worried that I won't be as good as her if she has a lot of experience."

"You are going to be great. Don't worry about it. Now get back on the dance floor," I told her. "I'll watch, and play wing woman if I need to."

I watched Chelsea dance with several women, and with one guy. I was pretty sure all the people she was dancing with were straight, but she was having fun and I was enjoying watching. All of a sudden a friend of mine, Chase, walked up to the table. I hadn't even seen him there.

"All these straight people in my bar," he tutted. "Don't you have a boyfriend?" He was laughing, obviously joking. He caught me mid sip of my drink.

"I do," I told him, "but I'm here playing wing woman for a friend." He looked out at the dance floor and asked who. I pointed at Chelsea.

"Oh you can tell she's straight," He said. I didn't hide that I was bi, but I didn't flaunt it either. Chase was aware that I was bi, and he was very open about the fact that he was gay. He had come out in high school, and his family had been very accepting. I knew he was lucky in that, but I still admired the courage he had to do it.

"She's Bi-curious," I said. "She was asking me for tips about a woman and I brought her here just for fun."

"Well she is dancing with a friend of mine who is straight and just here for the show. I practically dragged her here."

"Well that's unfortunate," I said and looked over. "Well, my friend just made it to first base with your straight friend."

Chelsea and this girl were making out on the dance floor. A few girls were watching them surprised. I assumed they were Chase's other girlfriends. He looked at them then back at me.

"It's always the super-goody-goody Christian girls," he muttered mostly to himself. Then he looked back to me, "And she's the sober one of the group." We both laughed.

Chelsea and Chase's friend danced for one more song whispering a bit to each other. Chelsea made a pouty face, and I knew the other girl had "remembered" she was straight.

"Oh no this looks brutal," Chase said. I asked if he would excuse me so I could go save my friend from embarrassment. I walked out on the dance floor acting as if I did not know Chelsea and then pulled her away from her new friend and started to dance with her.

"So how was that?" I asked.

"I made out with a straight girl, so I guess I'm taking baby steps."

"Do you still want to try to find a woman to go home with?" I asked.

"I don't think so, I've been rejected enough by straight women tonight. This gay bar is a bust." She chuckled as she said the last part. I took her back to our table and we sat down.

"Was the last time you got laid with Chris?" I asked. She looked a little sheepish then nodded yes.

Chelsea is a hottie. She was 5'8" with long legs and a trim body. Despite never going to the gym she was in good shape. She wasn't toned, but she was slim. She had a pixie cut which was dyed platinum blonde. She had a cute smile, and a small pointed nose.

She also had a set of DD's that looked amazing. They were fake, but that didn't change the fact that they looked amazing. I'd be lying if I said I hadn't imagined playing with them. I had never felt fake tits before and was more than a little curious about what they felt like.

It was hard to imagine she hadn't been able to land a guy in the past three months, except I knew she was pretty shy and very much an introvert. She was also very focused on her grades. And I mean VERY focused on schoolwork. The reason she had been fuckbuddies with Chris was it took something off her plate. She could get laid without having to worry about finding a hookup or maintaining a relationship.

We each had another drink and were both starting to get tipsy. I blame the alcohol on what I did next but am very glad I did it. I remembered Chris' joke about a threesome and decided to go for it.

"Ok Chelsea," I grabbed her hand. "We're going." I led her away from the table, paid our tab (the disadvantage of a gay bar, no guys bought our drinks that night), and started to walk out.

"Where are we going?" she asked.

I turned to her once outside. "Chris' idea about the threesome. Let's do it. You get a good fuck which you need. You get to be with a woman for the first time who is open to giving you some tips without judging, and I get to be with a woman for my first time in several months."