tagGroup SexGuessing Game

Guessing Game


Just after college, I met this incredible girl Carol where I worked, and we began dating, and after a few weeks, things were getting a bit more serious. I don't think either of us intended to have anything major serious, but we really enjoyed each other's company and were having lots of great sex. We were in our 20's and not really thinking long term.

I was living on one side of Cambridge, and she lived near downtown Boston with her sister Leslie, who was rarely there. And Carol and I developed a small group of friends with whom we did things regularly together on weekends. One of these friends was Debbie, who was a very sexy and fun woman, single but 'always looking' for the right man. She never seemed to be without a boyfriend, but for a while, she was having a dry spell with male company.

Carol and I were spending lots of nights together, mostly at her place because her sister wasn't there. I think she did a lot of traveling with work and my place was small and on a less convenient pathway where we liked to hang out. She was a very sexy lady indeed, with a tall, trim body and rarely wore any undergarments. Many times we would go out and she would just have on a mid thigh length dress. That's it. It didn't bother her that her small breasts were visible, as were her prominent nipples, that seemed constantly hard. She rather liked the attention I think. I told her a number of times how much I liked looking at her and how sexy she looked. And I knew other people looked at her when we walked into a store or restaurant because she was so hot and carried herself in a very sensual manner. Even though we had been together for 5 months, and had been naked together countless times, I never tired of looking at her and looking at other looking at her, and trying to catch a glimpse up her dress or look at her breasts through the sides and arm holes of her dresses. She was as much of an exhibitionist as I was a voyeur...that's probably why we got along so well and had such wild sex together.

Even when we were alone together, Carol would walk around naked, or just with a tee shirt on, not really caring who was watching. Or perhaps it was that she cared that people were watching and enjoyed it all the more. I tried to be discreet when Leslie was around, but since they were sisters, there wasn't much modesty. And a number of times, I saw Leslie naked too, since there was only one bathroom and Leslie enjoyed the 'accidental' encounter in the bathroom when she emerged from the shower, not having fully closed the door and I was passing by.

I think Carol purposely left her bedroom door open when Leslie was around and I was staying over so that Leslie could see us having sex and a number of times, I though I could sense some shadows in the hall way outside our room, and more than just imagined Leslie in the darkness.

And then one evening, Debbie, Carol and I were hanging around the apartment and were getting a bit bored. We were drinking more than usual and I was serving up a constant supply of Margaritas, and the evening wore on, we were getting more than a bit sloshed. Then Debbie produced some weed, and offered it around. I declined, saying that if affected me weird one day a year ago, and didn't want to experience that again. When pressed for details, both Debbie and Carol were anxious for an explanation. Never having shared this with my girlfriend, I didn't want this to be the time of place to explain a bit of an embarrassing situation. But the alcohol was loosening my inhibitions and Carol said,

"If you tell us, I'll make it worth your while later tonight."

"Just what are you offering my dear..." I asked smiling, thinking about all the options from which I could choose my payment.

" I'm sure I could come up with something..." Carol said, sitting in one of her short dresses, legs exposed up to mid thigh, and slyly pulled the dress up a bit higher.

Debbie was sitting next to Carol on the sofa, and the nuance of Carol's activities were not lost on her.

"Yeah, let's her it Dave, what you would want Carol to do. I want to hear what happened with the weed too." Debbie added.

They could sense my reluctance and were teaming up to pounce on my vulnerability.

"How about one of 'those' massages you say you like?" Carol offered, again with that sly, sultry smile.

"What's one of 'those' massages?" Debbie asked, giggling, clearly feeling good from the cold drinks we were having.

"He likes me to have oil on my hands and rub his back, then turn over so I can slowly stroke his cock and then have me fuck him from on top." Carol quickly and without reservation offered.

"Sounds like fun Dave....wouldn't that be worth a bit of disclosure?"

"Does sound fun...but perhaps Debbie would feel a little left out?" I said, my mind filling with images of both of them rubbing me all over with oil and four hands and two mouths and two pussies to delve into...

"That wouldn't be a problem," Debbie said, not exactly being clear with what she meant.

"C'mon Dave...tell us what happened...we won't tell anyone and we wouldn't make you smoke any if you didn't want...we might partake though." Carol smiled, looking at Debbie and nodding their heads in agreement.

"Allright girls...go ahead and get yourselves going...I'll tell you. Carol's offer sounds pretty good to me."

Debbie went to her purse and got a joint and lighter our and started to smoke, inhaling deeply, and passing the cigarette to Carol, who also inhaled, held her breath, and then both exhaled deeply.

"So what happened that you've been reluctant to tell?" Carol asked.

"Well, it's a bit odd...but last year, this girl I was dating had some weed, and when we smoked we got good and high and then were screwing, and screwing real good."

"Sounds normal to me...I thought you were going to say you couldn't get it up or something..." Debbie said, inhaling again, and passing it back to Carol, who did the same. I was meanwhile drinking the Margarita, watching the girls get high on top of the alcohol buzz.

"But the problem was that we were screwing pretty good for a while and after about 20-30 minutes, I couldn't get off."

"What do you mean?" Carol asked, eyes getting glazed and clearly enjoying herself. "I know that's never been a problem with you," she smiled, knowing full well that we were very compatible sexually and she was quite adept at getting me off.

"Well, I just couldn't come...something about the weed I guess."

"Doesn't sound like a problem to me. Most guys don't last 5 minutes." Debbie said, and both girls broke into bouts of laughter.

"Yeah...sounds like it was quite worth while for your girlfriend...I'll be she liked your staying power." Carol said, resuming their reams of laughing, now both with tears running down their faces.

"Perhaps so...but it didn't feel good after a while...sort of hurt when I was all bottled up."

"Poor guy...all blue balls..." Carol said, and then they were inconsolable with laughter, literally falling over each other on the sofa while I sat there starting to laugh too, mostly at their amusement even if was a bit at my expense. It was contagious.

"I bet I could have gotten you off...I've learned what works, haven't I?" Carol said when she could finally catch her breath, and managed a wink at me through her haze of a drunken buzz.

"I'll bet I could too." Debbie said, all serious like, which did nothing but get them laughing and doubling over with laughter.

"You guys think you're so hilarious, don't you?"

"Yeah...we're pretty funny...more fun than you can handle..." Debbie said.

"I think it was just that my senses were a bit dulled by the stuff."

"And so your senses are pretty keen now, are they then?" Debbie asked, also eyes glazed by the combination of the tequila, marijuana and laughing for the last few minutes.

"Well, the tequilas are making me feel pretty good, but I think I can tell what's what."

I could see Carol just sitting there, smoking and taking in the conversation. I thought she was stoned out but her wheels were turning.

"So you want to prove that to us Dave?" Carol finally asked.

"What do you mean?"

"We've been together for a while, right?"


"And you and I have fun together, right?"

"Right again," I said, not sure where Carol was going with all this.

"And you like what we've got going on...in the bedroom that is, right?"

"Yeah, sure."

"And you fancy Debbie a bit right?"

I looked at Carol, and then at Debbie, and back at Carol, not knowing what's the right thing to say, not wanting to offend Debbie and not wanting to tell my girlfriend that I had the hots for her friend.

"Sure...Debbie is pretty and hot, but not as much as you babe," I said, hoping that I wasn't putting my foot in my mouth.

"And we look a bit alike, don't we Dave?"

I looked at them again, and they were roughly the same build...5'6", tight, toned, medium breasted....Debbie was a bit more full in the tits department...same long hair, Debbie reddish hair and Carol with brown hair. A bit similar, but different at the same time.

"Some is the same, some is different," I said.

"Well, how about a bit of a game then?" Carol asked.

"What kind of game?"

Debbie was sitting quiet and absorbing the dialog, and I couldn't tell if she knew what was going on in Carol's head or if they had discussed this before. She was looking a bit buzzed out.

"So Dave...you think you've got our senses about you enough to tell us apart?"

"I'm not sure what you mean."

"Do you think you could tell Debbie apart from me?"

"Sure I can...you guys are different...I'm still not sure what you're getting at babe."

"Well..." she said., eyes narrowed in the smoke. "Here's the deal."

Debbie and I were listening intently.

"You sit there with a blindfold on and at first sit on your hands. Debbie and I take turns touching you and letting you touch us, and if you can tell the difference, you'll get the reward we were talking about before, but with both of us"

"Intriguiging... sort of a guessing game, but with you two taking turns..."

Debbie hadn't said a word in a few minutes and then said without further ado,

"I'm in. I don't think he can do it."

"Yeah, I don't think so either, " Carol added.

"You guys feel pretty sure you can fool me, huh?"

"Yeah, we do," Debbie said, looking at Carol. "We can pull it off."

"And if you can't, you have to give each one of us a 30 minute massage...just to make it interesting."

I thought about this for a couple minutes...didn't seem like I could lose either way because having my hands on them for an hour didn't seem much like a loss, and playing the game Carol suggested was immensely exciting.

"You're on." I said, emphatically.

Game on.

So Carol jumped up and ran to her bedroom and came back with a scarf.

"Ok, big Dave...sit here," she gestured to the sofa where they were sitting and I got up from the chair adjacent and sat between the girls. Carol proceeded to tie the scarf around my head, and thoroughly blindfolded me so I couldn't see even a glimpse of light. She pressed my hands to my sides and guided me to sit on my hands.

"You do this pretty well...had a bit of practice, have we?" I asked.

"Perhaps..." Carol giggled and then I was sitting along on the sofa. I heard Debbie giggle too and the two resumed their giggling fit, I presume seeing me blindfolded at their feet.

"I guess there's more to you than I knew, eh babe?"

"I guess so...so here's the deal...one of us will touch you or you touch us, and you have to guess who it is. If you guess right, one point for you. If you guess wrong, one for us. First to seven wins. Ok?"

"Ok with me...bring it on girls..."

"Here it goes...I can feel that massage comin', can't you Deb?"

"Ummm...sure can..." more giggling...

After a bit of whispering, I soon felt a pair of hands touching my head, rubbing my hair and then my neck and ears. I felt goose bumps on my arms and though I was starting to get a bit excited, I was trying to feel and smell a difference between the Carol I knew and the Debbie I was anxious to know.

The caresses continued and down to my upper chest and then felt a couple buttons on my shirt open, and stroking the hair on my chest but avoiding my sensitive nipples...for now. I leaned forward towards the direction of the arms trying to smell the performer, but all I could smell was a faint smell of pot and a hint of hair draping against my ears. Could Debbie's hair reach like this? Was this what Carol would do? Wouldn't Carol start this off?....

...yeah...must be that....must be Carol starting this because Debbie wasn't sure of the rules exactly. Carol would tell her what to do and where to touch me, but not yet.

"I know...this is you Carol...I can tell the touch of your hands."

"Right you are my Dave...right you are..." Carol said, a bit of disappointment in her voice. "1-0 you."

"Maybe just a lucky guess..."

"Yeah, that's right...just a lucky guess."

Then after a few moments pause, I heard some more giggling from a few feet away, and then I felt the pressure of someone next to me on the sofa. My right arm was pulled away and guided to a smooth leg. I stroked the calf and then the knee and thigh, and tried to figure out whose this was. Felt smooth and toned...this was a bit tougher than the last one. I tried to tap into my memory of Carol's legs and then picture what Debbie's would feel like. Felt way familiar, but would Carol go twice in a row? Must be Debbie's turn. But would Carol let me stroke Debbie's leg? I had to just guess...

"I think this is you again Carol...feels like your smooth legs..." I said, without as much conviction as prior.

"HA!...wrong this time Dave," exclaimed Carol. That's our good friend Debbie who your were copping a feel."

"1-1 Dave..." said Debbie..."this is getting fun."

"Ok girls, I'm ready again. "

More whispering and a couple tokes a few feet away, and then the giggles again. They were just plain funny hearing them carry on.

Soon I felt two hands rub my legs up to the hem of my shorts. I felt the soft skin of small hands massaging my calves and then my knees and thighs, getting tantalizingly close to my groin, where I felt a distinct stirring.

This was way hard, I mean telling who this was was way difficult. Could be either of them. Nothing distinctive...I tried to smell who was closer, but again was met with the same smell of the weed. Perhaps this second-hand smoke was getting to me too...this was going to be an all out guess.

"You guys are getting sneaky on me...this is going to be tough...but I think this is Debbie's leg."

"Wrong again Dave..." said Carol. "I was hoping you could tell who was giving you the feel."

"2-1 us," said Debbie... "This is really fun now... we've got him now, huh Carol," which led to another laughing fit from the two.

"Back on the hands Dave...we're getting you now," said Carol. "Good luck on the next one."

Someone pushed my hands back so that I was sitting on them and offered me a sip of my Margarita. Then a few moments of them discussing their game plan and I felt a pair of hands unbutton my shirt a bit more and pull the tails from the hem of my shorts. Then the person kneeling next to me was against my side and I thought I could feel some breasts against my arm. Were these Carol's boobs or Debbie's slightly larger ones? Was there a bra there? Was Debbie wearing a bra before? I knew Carol wasn't. Further challenging my guess was that these hands were now caressing my chest and stomach and I was getting way turned on. I was squirming now trying to give my cock some room to grow, and I felt the hands caressing my stomach and then lightly at my nipples.

I now had a full erection and I'm sure it was quite evident in my shorts. My thoughts were getting a bit cloudy and I was struggling with this one. Another pure guess. The last one was Debbie and perhaps Carol told Debbie what to do. They were pretty stoned so I couldn't rule out that Debbie was again put up to the task.

My cock was rock hard and the caresses continued and my nipples were hard and sensitive and my stomach wiggled under the fingernails of the gentle fingers touching me all over. That did feel a bit like Carol's touch...

"Carol...that's you..."

"Good one Dave...you're right...just a guess right? You weren't sure, were you?"

"I could tell your touch Carol," I lied...it was indeed a lucky guess.

"Well, we're tied Dave...2-2. You're giving us a challenge," Carol said.

More whispering and game planning and clothes rustling, and another drink to my lips.

I felt someone pull my left hand from underneath me and pulled towards the unknown. I felt myself drawn towards a thigh and then a bare ass. She let my hand go to wander a bit and I felt around the firm leg, the ass. I squeezed and probed, not only liking the feel but trying to gauge the woman. A great feel...firm, muscled and toned....but that could be either. No voice or laugh to determine either. I tried to feel a bit around the front to see if this would help me, but she didn't let my hand get that far.

Wow...tougher than I thought. Part of me loved the game and getting to cop a feel, especially if this was Debbie's naked leg and ass I was feeling. But I wanted to win and get my prize and also know that I could tell my girlfriend from another woman.

But this was again another guess...I was glad the odds were no worse than 50-50.

"Carol's leg..." I said, with feigned confidence.

"Right you are Dave...right you are..." Debbie said, withdrawing to discuss strategy.

"3-2 you Dave...you're getting good," Carol said. "We're gonna get tougher I guess."

"Bring it on ladies..."

Whispering, giggling, inhaling again...more giggling..."Hold still now," said Carol from where they were strategizing.

I felt my hands being pushed back to sit on them, which I obediently did. Then I felt someone straddle my thighs and felt skin against my face. I instinctively leaned forward to press against the smooth skin that I quickly knew were bare breasts. I tried to move my head back and forth and get a sense of the size of these wonderful orbs in my face, but hands quickly held me still.

Debbie's breasts, though I have never seen naked before, were larger than Carol's, but not by much. I sure had Carol's in my face and mouth before to know what hers felt like. I felt the skin on my cheeks and then a nipple across my lips. I opened my lips without thinking and then quickly felt a touch to my mouth and pulling away, telling me that I couldn't use my lips to help. That would have given me the answer.

But these felt just a bit larger than Carol's...a different aroma...too close to be clouded by the smoke that their hair felt from the weed. They couldn't mask this proximity...I knew the answer but I wanted to prolong this sensation, of Debbie's breasts against and around my face. I would be lying if I said I'd never thought of this before, and though I couldn't use my mouth, and tongue and suck these nipples, these were Debbie's glorious tits in my face.

Then they pulled away, and I sighed..."Debbie...for sure Debbie..."

"Right you are Dave...good thing you got that right," said Carol, with some sincerity in her voice.

Right indeed...needed to store that one away for a while.

"4-2 you," said Carol..."You're proving to be a touch customer. I guess we're gonna have to get serious now..."

Another sip or Margarita was offered and accepted. Then the whispering and a few moments later, I felt someone sit beside me to my right side, and start stroking my inner thighs. I was still way hard and squirming a bit in my seat, but enjoying the game and my lead.

Then the hands were stroking higher towards my crotch and inevitably to my aching erection tenting my shorts. They unbuckled my shorts and reached in and I gasped at the touch of a hand on my throbbing cock. I was going to struggle with this one. I was so turned on it was hard to concentrate on making a good guess.

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