My Wingman Has Great Boobs [MF] [F] [swinging]

(Yes, it’s long. But good stories often are. All * names have been changed to protect people’s anonymity. Skip to the *** if you don’t want backstory, but you’ll miss the context. And there’s more than one round of sexytimes involved.)

So let me tell you about Candy*.

She’s fucking hot.

Okay, a little more? Candy is about 5’10”. She’s done a lot of modeling, including some nude modeling. Early 30s. (A few years younger than me.) She’s got amazing long legs, perfect and sexy from a decade plus of dance. She’s thin, gorgeous, a mix of ethnic background that makes her turn heads even in a t-shirt and denim shorts and no makeup, a +3 ass of perfection, and beautiful 34-B boobs that don’t need a bra.

So, to sum up, Candy makes guys drool.

She’s also my best friend. And my wingman.

And make no mistake, I am not oblivious to how sexy my best friend is, but from the moment we met we’ve just bonded as friends. She can totally be just one of the guys. She can fart and burp with the best of us. She’ll point out the hot server at Friday’s to me in case I missed her.

Candy and I met about three years ago and instantly realized we were meant to be friends. In the last three years we’ve coached each other through a ton of good and bad relationships on both sides. I’ve been open with my present partner for a decade, and when we met she was with a long term partner and they were considering non-monogamy. I introduced them to a couple of the local lifestyle clubs, they explored it a little, but eventually they broke up for reasons having nothing to do with that.

She just ended a year plus relationship that was very emotionally involved, and has made me promise I will not let her decide to date for at least six months.

About a month ago I got a message from a friend on Facebook from New York that she and her new boyfriend were going to visiting our town in early August and they were interested in visiting a lifestyle club for the first time together. We checked dates and availability and decided on this previous Friday. I messaged Candy and asked if she wanted to join us so I wasn’t a third wheel, not to mention admission for single males is almost prohibitively expensive. She could be my wingman and if she saw someone she wanted to have some fun with I’d be hers.

If nothing else, she definitely has a voyeur side to her, and loves to watch. And while she’s mostly straight, she especially loves watching women masturbate, which we totally have in common. I mean, who doesn’t?

A couple days before our planned excursion, my friend from out of town backed out. She was into it, but her boyfriend was anxious about the experience, and wasn’t comfortable with the idea of going with people she knew. Totally understandable. I talked to Candy about it and we figured we’d still go, at the very worst it’d be fun.

So, on to this past weekend. Our plan was that I’d come by her place about 9:30, we’d leave around ten, get to the club around 10:30. At 8:30 she messaged me to say she was sitting around with nothing to do and wanted to just get dressed. So I grabbed some nice clothes and told her I’d be over early.

When I got to her place she was getting her makeup ready. For a dress she’d chosen a sexy but not over the top strapless mid-thigh skirt that showed off her legs. (Oy, those legs.) No bra, but with her you usually can’t tell.

I slipped into her bathroom to change into a nice dress shirt, vest and tie, and my nicest pair of jeans. As it turns out later, I was overdressed.

On the drive down we managed to get lost just once for a couple minutes, and then got there a little earlier than I expected. The lobby wasn’t yet busy. We checked in, noticed there was an adult boutique off the lobby selling lingerie and sex toys, and headed into the dance floor.

Now, she’s a dancer. I am not. I have no rhythm. So she grabbed a vodka and lime juice at the bar and we settled down on the side to people watch.

At this point, I might as well do the expected and describe myself. I am an okay looking guy. 5’10”. 175 pounds. Short brown hair. I don’t turn heads but I also consider myself a pretty damned intelligent, funny and creative guy. But a decade in the lifestyle has taught me that 90% of the attention I get comes from having a hot woman sitting next to me.

Our first 20 minutes didn’t really reveal too many couples or anyone that either of us were interested in. I asked if she wanted to explore the play area since she hadn’t been there in a couple years and it had changed. We walked out of the bar, across the courtyard separating the bar from the back rooms.

It had actually been almost a year since I had been there, and they’d really renovated the back rooms. One area had been turned into a decent sized dungeon. I’m not heavily into BDSM but it certainly can be interesting to watch when a couple is comfortable with it and trusts each other.

In the middle of the room, one couple was in the middle of a very elaborate act of Shibari, Japanese rope bondage. He was fully clothed. The woman was naked, standing, and her partner had obviously been at it for a while, as she was already surrounded by several elaborate rope twists and turns, her breasts squeezed out through the knotted bindings. They were quiet, focused. We watched for a couple minutes. He continued to work on the ropes, no sexual contact yet. I was more impressed than turned on, but the detail and trust between them was pretty fascinating. I had friends a few years back who had some intermediate experience and knowledge with Shibari, they offered to teach myself and my primary, but we never found the time.

Candy leaned over and asked if she could touch the woman’s feet. Her partner asked that we didn’t, as she was in a very vulnerable position and she preferred he be the only one to touch her. We of course respected this.

In the back of the room was a large X with restraints at the four edges, a Saint Andrews Cross. An older white man, 50s perhaps, was securing a black woman, 20s, by her hands and feet to the Cross. We walked over and watched quietly from a few feet away.

***

The woman was wearing a tight, short dress. As we got close, we realized how tiny she was. A little over 5 feet, perhaps 5’2″, and probably 100 pounds soaking wet. (Spoiler alert. She was about to be.) As she was secured, he pulled the top down to reveal two enormous breasts, probably DDs at least, and fake if still impressive. They defied gravity and mocked Galileo. Her nipples were already rock hard as he smacked them. She kept leaning over to kiss him but he denied her, whispering in her ear something we couldn’t hear.

I slid my arm around Candy and hers around mine as we watched. “You enjoying this? I know she’s your type,” Candy whispered, as she knew I really liked petite girls.

We watched some more. He next slid her dress up, not surprisingly to reveal she was not wearing panties. Her clit was already swollen, engorged. He began to slide his hands up and down her thighs, occasionally fluttering by her clit and then moving away, teasing her. She whimpered, pulling against her restraints. He slid his fingers inside her pussy, first one, then a second, and began to finger her forcefully for a few seconds. Then he would pull them out as she begged for more.

“Okay, I’m pretty hard now,” I confessed to Candy, still sitting next to me, her hand now sitting on my knee. “I don’t blame you, this is pretty hot,” she answered, sipping her vodka and lime juice. The room, we both noticed, was really hot. The A/C didn’t seem to be on.

The woman began to breathe pretty rapidly, and I looked back over to see him rubbing all around her clit, and then slide his fingers inside her pussy, cover them with her wetness, and then slide back out to massage her clit. She was enjoying it immensely, and he would occasionally still grab her breasts roughly, pinch her nipples, and whisper something in her ear. She looked over at Candy and I, sitting on a couch a few feet away, and smiled. She whispered something to her partner.

He turned to us, smiling. “Would you two like to play with her?”

My erection answered for me, but I turned to Candy and asked what she wanted. “You go play, I’ll watch. Have fun.”

Like I said, folks, she’s an amazing wingman.

I walked over to the woman. I smiled, she smiled back. “Hi,” I said, “do you have any rules I need to know about?”

“No,” she said, “Whatever you want.”

I slid my fingers down and started running them all around her stomach, her thighs. I grabbed a handful of an amazing tight and round ass. “You have an amazing body,” I whispered.

“Thank you,” she answered back.

“I can’t wait to make you cum,” I whispered, as I leaned in and started kissing her neck, her ear, running my tongue around the earlobe and softly teasing her clit. She moaned heavily, and arched her body as her way of asking for me to keep touching her clit.

I grabbed one of her breasts with one hand, and with the other, slid a finger deep inside her pussy. She let out a huge moan, muttering “Oh God, Oh shit, Oh fuck.” If she had been wet before, she was dripping now. Spread wide open, helpless, and with her partner watching her get fingered by a stranger. I didn’t know her name, and she didn’t know mine. I slid my fingers inside, getting them wet, then stood up and put them in her mouth, so she could lick them clean.

My erection was hard enough to cut diamonds, I’d bet. Here I was, fingering this fucking hot sexy woman who I’d just met, and Candy was watching…oh, yeah, at this point I actually did glance back at Candy. The woman’s partner (whose name I never did get, so we’ll just call him Jim) was sitting next to her on the couch, his arms softly caressing her shoulders. I matched eyes with her to make sure she was okay, she saw that and smiled. “I’m fine,” she mouthed.

I pressed my hard cock, through my jeans, against the woman’s thighs. She pushed back, as best as she could in the restraints. “Oh my God, you’re really hard,” she whispered.

“Yeah, you did that. Do you like that? That seeing you naked got me so hard?” I asked.

“Mmm hmm,” was the response. She didn’t say anymore as I slid two fingers inside her dripping wet pussy and started rubbing her G-spot. Her eyes closed and she kept muttering “Oh shit, oh fuck.” I kept rubbing inside her, faster and faster as her breathing quickened.

“I’m gonna…I’m gonna…” she said through clenched teeth as she built to an orgasm so strong I could feel the pulsing inside her. I kissed her. First passionately, tongues, and then softer, more sensually. It may be silly to talk about kissing as important when you’ve just made a stranger cum while secured in bondage, but I have always loved kissing in the middle of hot sex.

I wasn’t done with her yet. I bent down on my knees, and ran my tongue around her pussy lips. She tasted a little bitter, but still good. I took her clit in my mouth and softly sucked on it. Her body shuddered. As I did that I slid a finger back up inside her, rubbing her inside as I sucked on her clit, nibbling it softly with my gums on occasion.

Her second orgasm didn’t take long. I had her wetness all over my chin.

“Thank you,” she said, and Jim was behind me again. I figured perhaps my time was over, and I’d have to find another way to deal with the erection of steel in my jeans. He leaned over to her and asked, “Do you want to suck his cock?”

“Yes. Please,” was her response.

That would be the right response, as far as I was concerned.

As he released her from the four restraints, I sat down on the mattress next to the cross. I looked over at Candy, who gave me a thumbs up and a smile. I unbuttoned my jeans and pulled down my boxers. I realized in my dress shirt, vest and tie, I was overheated as fuck, so I quickly undressed. In the minute it took me to undress, the woman had dropped to her knees and was sucking her partner’s cock. I didn’t want to interrupt, so I put a hand softly on her shoulder to let her know I was ready if she was still interested. She looked back at me, and slowly pushed me back onto the mattress, then lay me down as she took my cock into her mouth.

I could spend three paragraphs talking about it, but even a bad blow job is amazing. And this was not a bad blow job. No, she was fantastic. She took me deep in her throat, and then would lick and caress my cock with her mouth.

In the middle of it, I looked over at Candy again, and Jim was sitting next to her, his arm around her shoulders. Her dress was pulled down and he was softly caressing her breasts. She looked content and safe.

She began to rub my cock against her breasts, against the hard nipples. It didn’t do it for me but she seemed to really enjoy it. I put my hands on top of her head as she again took me in her mouth.

(To answer the age old question of why guys put our hands on women’s’ heads as they go down on us, the answer is it keeps us from applauding.)

I pushed her down onto my cock again, which she took, hungrily, deep. It felt fucking amazing.

Jim was once again behind her, and I wondered for a second if he was going to fuck her from behind as she blew me, but instead he said to her, “Do you want to fuck him?”

“Yes, please. I need his cock inside me,” was her response. And my ego grew three sizes that day.

“I need…a condom,” I said to him, as I was lying naked on a mattress with her saliva all over my crotch.

(I didn’t do it on purpose, but later I realized sending a guy to find a condom so you can fuck his girlfriend is a pretty badass move.)

She leaned in close. “Is it okay with her?” she asked, looking over at Candy.

“Yeah, she’s fine with it,” I answered back. I was realizing I seriously owed Candy one. She had majorly accomplished the duty of a good wingman.

He returned with the condom and I rolled it on. She pushed me back down on the mattress and climbed on top of me. Holy crap she felt amazing. So wet, so good. She pulled my hands up to her tits and had me squeeze them as she slid her clit back and forth over the tip of my cock, then finally sliding me deep inside her. She didn’t so much bounce as she rocked her hips back and forth, her clit never breaking contact with my skin.

After a couple minutes, on one rock, my cock slid out of her, so I got up and flipped her over, a little rough, and she squealed. I laid her down on the mattress and put her legs on top of my shoulders. I ran my hands down those thighs, those calves. I’m a leg man, and although I wasn’t going to spend time on her legs when she was naked and fucking me, holy fuck she had amazing legs. I slid my cock inside her and picked her ass up so I could go in really deep.

And that’s when she started making sounds that made me proud to be a straight man. Moaning, cooing, whispering “Holy shit, holy fuck” as I pounded her. I leaned down and kissed her, whispering how much I loved her pussy, how much I loved fucking her. I looked over and Candy had moved a few feet away from Jim, giving him space. His pants were down and he was jerking off, watching me fuck his girl.

“Do you like?” I asked her, grinning.

“Ohmygodyesodntstopfuckingmeiloveyourcock” she answered without breathing.

No, I don’t have a huge cock, I’m average, but I know what I’m doing and I know how to make a partner feel good.

Jim came over and put his face down next to hers. “You like it?” he asked her.

“Yes, I love his dick. I love his cock,” she answered, “Thank you for letting him fuck me.”

He stroked her face and I started pounding her harder. Thankfully that 5 hour energy drink I’d taken before picking up Candy was working.

“I need your cock, in my mouth,” she grunted, as she reached out and grabbed him. He repositioned himself and stuck his cock in her mouth. She sucked it hungrily. I started fucking her harder, trying to cum, but I’m not used to condoms with my primary and so it wasn’t happening.

But she was making amazing noises, so I fucked her harder, faster, and then, when I started rubbing her clit, she exploded, cumming hard as I fucked her and she sucked Jim’s cock.

I realized I wasn’t going to cum soon, so I slid out and sat down on the edge of the bed.

I started getting dressed. After a minute I leaned over and gave her a soft kiss on the lips. “Hi,” I said, and I introduced myself.

“I’m Tyra*,” she said, smiling. It was the first time I’d seen her smile. She was really pretty.

Tyra and Jim walked out of the room. I took a minute to recharge. Candy was over watching the first couple with the ropes again, not touching. The woman was suspended from the ceiling and her guy was using a vibrator to get her off. The ropes were crisscrossed across her body and her legs were spread in such a way that her pussy and clit were wide open to him no matter what she did. I could understand why she had been so particular about no touching.

“So, that happened,” I said to Candy.

“That was really hot. I got really turned on watching you.” She smirked. “Oh, by the way, nice dick.”

Oh yeah, funny enough, I realized she’d never seen me naked. “Thanks. I’m average, I guess.”

“No, bigger than average,” she answered.

“No, I’m not–”

“Yes, you are. And trust me, I’ve seen a few dicks in my time. Plus, you know what you’re doing, that was obvious. It was really hot.”

“Thanks,” I said. “I’m sorry he wasn’t your type, or–”

“Oh, no, he was really nice. He kept telling me how pretty I was, which is always nice to hear, and he totally respected I didn’t want to do anything more.”

“Okay,” I said, “But I’m totally dehydrated. And sweaty as fuck. Can we go get some water before we decide what we’re doing?”

We walked back outside and over to the bar. I got myself a glass of ice water, and it was among the most refreshing things I’ve ever had. We sat down in the same spot we’d sat in an hour earlier.

“So,” I said, “What did you want to do? Did you want to go, or…?”

“I don’t know. I do know I’m really turned on.”

“Did you want to…you know, take care of that?”

She thought about it. “I didn’t bring a vibrator.”

I tried to remember if I’d seen any toys in the play area. “I don’t know if they have any toys in the back area. The old club we used to go to had a Sybian.”

“What’s a Sybian?” she asked.

“It’s like a $1200 vibrator, it kinda looks like a saddle, and you sit on top of it.”

“Twelve hundred dollars?”

“Yeah. I’ve seen women sit on it and their heads basically explode.”

We decided to go back into the play area and see if there were any toys back there. We’d seen multiple sanitizer stations so we thought they might have some. But we didn’t see any in the main rooms or the dungeon, and there weren’t any couples that we found interesting to introduce ourselves to. We asked one of the attendants about it, and she said that people were supposed to bring their own toys, but reminded us of the boutique in the lobby.

We decided that we’d go check out the boutique and after I ran back to the car to drop off my vest and tie (no way I was putting them back on), we could then look and see if there was a toy she liked in the store. If she found one, I’d buy it for her as a thank you.

In the corner of the store was a Sybian, so we spent a couple minutes talking about that with the clerk. Our price range was about $1200 less than that, so she found a little bullet vibe that she liked and I bought it for her. We remembered to buy the batteries as well.

As walked back to the play area I asked how she wanted to do this. Private room, middle of the play area, or what?

Between the lobby and the bar and the play area was the pool area. As it was a clothing optional pool several couples were sitting by the pool naked, some being intimate, some not. We noticed Tyra and Jim in a pool chair by the shallow end, cuddling.

“Over there,” Candy said, and she pointed to the shallow side of the pool.

We walked over and sat down. She took off her shoes and pulled the top of her dress down so her breasts were out. They really are pretty gorgeous. Perfect for her body. I put the batteries into the vibe and handed it to her, she gave me the speed controller. She slid her dress up so it along her waist and put her feet in the pool. I turned on the vibe and she slid it into her panties.

“Sit behind me,” she asked. “I like to be groped when I masturbate.”

See, friends share important info.

I slid along behind her and rolled up my dress sleeves. I reached around and caressed her breasts.

“Does it go higher?” she asked. I pushed the button a couple more times and 4 bars lit up.

“Full power,” I said, and resisted the urge to make a Star Trek Scotty joke.

She leaned her head back against me. She started to breathe heavier, quicker. She grabbed one of my hands and put it right on her breast. She took the other hand and put it across her throat.

“Not too hard,” she said, “but I’m a screamer. When I get close to cumming, cover my mouth so I don’t wake up the entire neighborhood.”

I looked up and saw Tyra watching, slowly fingering herself while Jim played with her tits from behind. We had given Candy a show, so it was nice to be returning the favor.

Candy leaned back even more to me, and I could see her moving the vibe around inside her panties. After a minute, she hiked up her dress, picked up her ass, and slid her panties off. I watched with wonder and she rubbed the vibe all over her clit. I leaned down and kissed her forehead, her cheek, and finally on the lips. My hand slipped down from her breast to her thighs, those amazing dancer legs, and I massaged them, closer and closer to her pussy because I wanted to make sure she was okay with it. I finally slid my fingers over her pussy and inside, to feel how wet she was. I didn’t have the right angle to play with her G-spot so I just kept rubbing her pussy lips and sliding my fingers under her clit to help with the vibe.

When I started doing that, it didn’t take much time. Her back arched, she pulled my hand tight across her mouth and she started screaming. I mean, full on screaming. My hand was tight across her mouth as she came, constantly, for about ten seconds. Wow, that was impressive.

I kissed her softly on the lips. “Feel better?” I asked.

“Mmmm hmmm. Thank you.”

She slid her panties back on, then pulled her dress back to starting position, and we waved at Tyra and her guy as they walked off.

At that point we were both kind of exhausted and overheated, so we sat by the pool for a few minutes and then decided to take one more turn through the play area to see if anything interested us in any way. Nobody did, so we started walking back to the car.

“I do have to admit,” I said, “I’m a little annoyed I didn’t get to cum.”

“I was wondering about that,” she answered. “If you want to take care of that?”

I thought about it for a second. “I would kinda like it if we flipped the script. You wanna watch me?”

“I’m okay with that. Where?”

I wasn’t as much of an exhibitionist as her, so we walked into the play area again and found an empty private room in the back. We locked the door and closed the blinds.

I got naked and laid down on the bed. I had been pretty much hard all night due to everything around me. Candy laid down next to me, and softly caressed my chest as I started stroking myself. She was watching very closely. I started whispering to her, asking her about what she had been thinking watching me and Tyra. She confessed how turned on she had been, how her clit had been aching. We spent a couple minutes discussing a mutual female friend that she knows I have the hots for, a woman that is stuck in an obviously passionless marriage who I really want to fuck but know I never will. Candy has expressed for me her interest in watching me “defile” this woman. So, you can see why we’re friends.

I asked her to pull her dress down so I could see her tits and she did, and we made out a little as I kept slowly stroking myself, enjoying the attention. “You have a really nice dick,” she repeated, and I was really appreciative of the compliment.

She slid her leg over mine, and the skin to skin contact was amazing. She started running her hands up and down my thighs, and I realized I was starting to get close. I couldn’t take it anymore, so I just grabbed her hand and put it on my cock and she started stroking it. It was amazing.

“Talk dirty to me,” I begged, nearing orgasm.

“I want you to cum for me,” she said. Over and over.

And I did.

After the orgasm died down, I started laughing.

“What?” she said.

“If this experience had happened to me, like it did, the first person in the world I’d want to brag about it would be…you. And you already know.”

She laughed. “Time to go home?” she asked.

“Yeah,” I answered.

We got dressed and finally headed out to the car. As we walked through the lobby the clerk asked us if we’d had a good time.

“Yeah,” I said, “After all, my wingman totally got me laid.”

Source: reddit.com/r/gonewildstories/comments/6tn8nv/my_wingman_has_great_boobs_mf_f_swinging