Taking [m]y then-[F]WB, to her first strip club--fun in the VIP room | 2016

This continues chronologically from my previous two stories (1, 2), although they are not necessary to enjoy this one, they are helpful, I think, especially if you want to get a sense of my developing relationship and love for Jill, which I know some people do.

It had only been about a month or so after Jill and I had first hooked up, with her confessing her desire to explore sexually and me taking that cue to fuck her in the coffee shop bathroom, and we had been meeting constantly since then, but things were still casual, to say the least. Jill was still extremely close (maybe best?) friends with my ex Mary, and Mary was still reeling from my ending things with her. In order to keep things from being to suspicious, we were still meeting mostly during working hours (side note: I ended up having to explain to my boss why exactly I was taking such long lunch breaks; he was an incredibly cool guy and approved of my getting laid as long as I still got my work done.) The problem with this arrangement was that I wanted more. I was clicking with Jill in a way that I never had with Mary, not to mention the fact that Jill was so fucking gorgeous it gives me wood just thinking about her to this day (5'8, long light brown hair, long legs, toned fit body, large C breasts, cute yet smoking hot face.) But I knew that a) Jill was terrified of Mary knowing that we were casually hooking up, let alone dating, and b) Jill was specifically looking to explore her sexuality, not find a boyfriend.

I couldn't help it though; I started scheming, without even realizing it consciously, to make her my girlfriend. And my first thought was that we needed to have a night out together, instead of casual fucking during the day, but the night out needed to be something that still felt casual, sexual, fun. I hit upon my solution one day when Jill confessed to me that she had been obsessed for over a year with this strip club near where she worked. I immediately jumped on it, and made plans for us to go there Friday night but, I casually mentioned, we should get some dinner first--don't want to ogle naked ladies on an empty stomach, of course! I was so excited after she agreed that I went down on her for another half-hour to get her to cum for the second time that afternoon.

I later learned from Jill that while she had a fun time at dinner with me, it still didn't transition her thinking of me away from Friend With Benefits and towards Boyfriend. I, however was almost completely smitten. We never lacked for conversation, the laughter was free and easy, and we couldn't keep our eyes off each other. I learned more about her studies (she was in grad school at the time as well as working), and I found them fascinating. We even talked a little about our families--I'm not sure how she didn't see this for the date it was. I was feeling bold enough on the way out of the restaurant to try holding her hand, and she let me. Now on to the strip club, which I know you've all been waiting for.

It turned out to be one of those rare, perfect clubs: not so sleazy that you feel like vomiting just from breathing the air, not so classy that you couldn't get away with a little more than most. And there was a nice variety of dancers as well--I never like those places where it's all skinny white girls with fake tits--this place had women of all colors and different sizes as well. We explored a bit, as Jill wanted to get a feel for what was going on, and I explained to her how the club works (tipping singles on the stage, public lap dances, VIP dances, etc.) I'd never been to a strip club with a woman before, and let me tell you: you are treated like fucking royalty. The waitresses love you, the dancers love you, even the bouncer seems more relaxed since he know you're probably not going to try anything with your girlfriend there. And being there with a woman as hot as Jill meant that I was getting extra special attention. We sat in the back but were getting hounded more than usual for dances.

True to my type, I had my eyes on this cute, fit brunette with natural B-cups named "Magic." I bought a dance from her for each of us, first for Jill and then for me. As if the naked flesh wasn't enough, watching Magic rub herself against Jill (and believe me, they are much more hands-on with women), gave me an instant and huge erection. When she got to me, Magic spent the whole time talking to Jill about how turned on I was, that she could feel my huge cock, and that I was probably going to fuck Jill good tonight. I nearly exploded in my pants; Jill was practically panting, and bright red.

Magic wanted us to get a VIP dance, but Jill wanted to explore around a little bit more. She had her eyes on the classic, fake-tits variety of dancer, never having seen fakes up close and personal before. I bought a dance for her from this one girl named "Destiny" or something. The whole time Jill was asking her about her fake tits, how much she loved them and wanted to touch them, and at the end of the dance Destiny just kind of leaned in and whispered, "Tell your stud to buy you a VIP dance and you can get all the touching you want." The VIP dances were not the cheapest, but I had some money and if you don't spend it on this, what are you saving it for? $150 later, Jill was off to the VIP lounge. I started to follow, but Destiny said she was sorry, but it was strictly one-at-a-time.

While I was waiting, imagining the goings-on, Magic came back and I bought her a drink. She asked me where Jill was, and pouted a little at learning that we hadn't bought VIP time with her, and that maybe I could make it up to her by buying a private dance. I told her that I would love nothing more, but I didn't want to do it alone, and I know about the one-at-a-time policy. This is when Jill, extremely, flushed, dress askew, started came back to our little area. Magic gave her a kiss on the cheek and asked to know what happened in the back. Jill blushed, but after some prodding, admitted that she touched Destiny's tits, and had her own tits felt up as well. Magic almost laughed out loud, but caught herself. "You two want to get some two-on-one time with me?" I looked meaningfully at Jill, who nodded yes. "We're not supposed to, but the manager doesn't care too much as long as the money comes in right, so $300 and we can go right now." I have rarely been harder in my life.

Magic took us both by the hands and led us through the blackout curtains into our private room. You know the kind, plush chair, red lighting, music thumping. Immediately, she removed her bra, now clad only in her panties. There was only the one chair, so she pushed Jill down into it, straddled her and grabbed me by my belt pulling me behind her. She started grinding herself back and forth between us, facing Jill. I reached my hand around and grabbed her tits, causing her to arch her back and rub her ass more fully against the huge tent in my pants. Jill took the cue and rubbed her hands up and down Magic's sides. Magic responded in kind, running her hands up and down Jill's body, then leaned forward and started sucking on her neck. Jill moaned and Magic ran her hands up Jill's thighs and under her dress.

I took a step back to watch the proceedings, but then Magic lifted her head off Jill's neck and looked at me with fire in her eyes and told me to get back here. I walked to the side of them, rubbing my cock through my pants with the palm of my hand. Magic's hand was working wonders under Jill's dress and Jill was looking back and forth between us, panting, moaning. Magic asked her if she could borrow my cock for a second, and Jill just moaned louder in response. I guess Magic took that for a yes, because she started undoing my belt and before I knew it her hand was wrapped around my bare cock, stroking it at the same time as she stroked Jill's pussy under her dress. That's all it took for Jill to cum, and cum hard, her hand on top of where Magic's was, grinding her hips against Magic's magic fingers, writhing in the chair.

Magic leaned forward to Jill's ear and whispered something, and then Jill was on her knees in front of me. Magic climbed into the chair, stuck her hand inside her panties and locked eyes with me as she started stroking herself. Jill lowered her luscious lips over my cock and I threw my head back and groaned. Magic started stroking her pussy even faster as Jill sucked me with enthusiasm, looking up at me, then over at Magic, then back at me. I'd been teaching Jill to give head over the past month, and she'd gotten damn good, especially considering my size. Her head bobbed deliciously over my cockhead while her tongue danced around it and her hand, slick with spit, worked the base of my shaft. It wasn't long before I felt myself building, and Magic seemed to sense it; she started fucking herself ever faster and telling me to do it, to fill Jill's mouth with my sticky cum. I warned Jill how close I was and she just kept going with renewed vigor. I dug my fingers in her hair and came in her mouth, pouring out a huge load. Magic made herself cum at the same time, straightening her back in the chair and letting out a quiet moan as she clutched her tit with her other hand.

Jill swallowed almost everything but a few drops landed on the carpet. She apologized, but Magic just gave her a kiss on the cheek and told her not to worry about, that a lot worse has happened around here. She told us her hours and that we should come back any time, which we definitely did. I took Jill back to my place and we fucked three times that night, and it was the first night she ever spent at my apartment.

Edit: the next part is up