A gay story: Losing a Bet This story involves a guy’s discovery of his bisexual nature and specifically involves male on male sex. As usual, if this is not your thing, please move on to a different story!
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I guess the cautionary part of this tale is to be careful when you make a bet. On the other hand, you may just discover things about yourself!
My friend Jane was always kind of wild. Uninhibited in almost any way, she and I had had more than one romp in bed together. She was the one who introduced me to my own cum when she gave me a blow job and immediately kissed me, fully pushing my entire load from her mouth into mine. Instead of hating it, I loved it, which was quite surprising to me. After that, we played lots of cum games – boob jobs where I would clean up the pearl necklace, cumming on her hairy pussy and then I’d eat it up, cumming on her ass and back and licking it all up. It even included one where she showed up at my door saying how horny she was, and she led me quickly to the bedroom and proceeded to feed me cum from her “date” with another guy right from her pussy! Again, I’d expected to be grossed out by it, but it turned me on completely! After eating her out, we fucked and I shot my load inside her, and then ate her out again!
One afternoon when she was at my place she looked at me with an odd look on her face.
“What?” I asked.
“Make a bet with me!” she replied.
“What kind of bet?” I asked.
“I can drink you under the table!” she said.
“Ridiculous!” I replied, “I outweigh you by almost 90 pounds!”
“Yep, but I’ll do it! First one to pass out or cry ‘Uncle!’ loses! What do you say?”
“What do I get if I win?” I asked.
“Well, once we’re sober again, I’ll be your sex slave for a week – anything you want, and I do mean anything!”
“What if, and it won’t happen, but what if I lose?”
“Then I surprise you!”
I just looked at her confidently and said “You’re on!”
We headed to the kitchen and my liquor cabinet and started the game, a shot at a time. One bottle of bourbon gone, we cracked the second. I was really wobbly by then, but somehow she did not seem as far gone as me. About half way down the second bottle, I could barely get the shot glass to my lips. She was really blurry, along with everything else in the room, when I poured the next shot completely down my chin.
“I win!” she declared.
“No, no, no, no, no, no, no, no!” I replied, completely slurred. “That wasss jussst a misssss – a misssss – a missstake!”
I tried a second time, but watched as the room darkened and I passed out.
Somehow, I woke up, naked in the bathtub, my head in a vice and fucking freezing. The shower was on and the cold water was raining down on me.
“Jane!” I shouted, “help me!”
She laughed as she came in from the bedroom.
“Are you awake?” she asked.
“Turn on some warm water!” I almost screamed, “this is fucking freezing my balls off!”
“You ran out of hot water about 10 minutes ago!” she said, still laughing.
I crawled out of the tub, and fed the porcelain throne my stomach contents. She helped me dry off and I stumbled into the bed.
I don’t know how long I slept, but when I awoke again it was dark outside. My head still felt like hell, and I got some water to drink, and went back to bed. Jane was softly sleeping and I cradled her as I climbed back into bed.
The next day I was hungover and barely ate, but Jane had a shit eating grin on her face.
“So, what’s my surprise?” I asked.
“You’ll see!” she replied, “but not today, you need to be far clearer in your head than you can possibly be today!”
A few days later, she called me at work.
“We’re going out on Friday evening!” she said. “I won’t tell you where, but dress in something that might get a little dirty, and I’ll come by your place at 10:30!”
“That late to start?” I asked.
“Yep! It’s someplace – special!”
I was filled with questions, none of which she would answer.
On Friday evening, I dressed casually and waited for her to pick me up. She was wearing a short black dress and looked sexy as hell, but would not tell me where we were going. In fact, once I was in the car, she put a blindfold on me.
“Hey, what the fuck?” I protested.
“All will be revealed!” was all that she would say.
We started driving and after about 20 minutes she parked and then opened my door and took my hand.
“Walk with me!” she said.
I stepped unevenly as she guided me along.
“Trust me, Mike,” she said, “I’m not going to let you walk into any walls or fall down!”
As we entered a door, I could hear dance music. We walked down a hall, and she lead me into a room. The dance music got muffled a bit, but was still prominent. She sat me down and I could hear the rustle of clothing, and then she began to unbutton my shirt and pull it off of me.
“What’s going on?” I asked her.
“Just preparation!” she said.
I began to get excited thinking that she was naked and taking my clothes off. Once she had my shirt off, she pulled my hands behind me and I heard the click of handcuffs and realized that I was now trapped. In our many games, we hadn’t really done any kind of bondage, so I wondered.
“Hey, what’s this?” I asked.
“Shh!” she said, “Nothing too extreme, just go with it!”
I then heard her knock on the wall, still wondering what was going on.
“Oooh!” I heard her say.
I could hear the sound of kissing and a muffled voice say “Oh, yeah, I like when you use your tongue!”
My mind was racing, and filling with images.
Suddenly, Jane’s hands were grabbing my shoulders.
“Come here, Mike!” she said pulling me.
I stood and she guided me over and said, “Kneel down here! Right, there’s a pillow down here – it’s OK, just kneel right here!”
She helped me get down on my knees. I was trying to “look” in her direction, though the blindfold meant that I could not see anything. I felt her hand caress my cheek and I could smell a scent that I could not quite place. I felt her kiss me and soon her tongue was snaking inside my mouth. I opened my mouth to accept her kiss and tongue, when suddenly it was invaded with a large, soft something. As I reacted, it pushed into my mouth, and I knew that it was the soft head of a hard cock. Jane’s hand was around behind my head as my reaction was to pull back, but she pushed me forward as the cock invaded my mouth.
“No, no, baby,” she said to me, “enjoy this! You need this! You’ve tasted cum before and you know you like it!”
Her hand ensured that I could not back away, and the cock began to move back and forth. Her other hand caressed my chin, and then was gone and then was back.
“You’ve already tasted this one!” she said. “This is Frank – you tasted him in my pussy last week, so you need to taste it at the source! Isn’t his cock amazing!”
The dick was pushing in and out of my mouth. The scent filled my nostrils and the sensation of his velvety head and otherwise rock hard shaft on my tongue and in my mouth was definitely different, and somehow highly erotic to me. I stopped pushing my head back against Jane’s hand and then slowly began to rock it back and forth over Frank’s prick.
“Oh, yeah, baby!” Jane was saying to me, “I knew you’d get into this! Frank, he needs your load, honey! I got you going, now fill his mouth! I want to kiss your load out of his mouth!”
Suddenly the cock jerked forward and it felt like the head swelled up even more and I tasted a bit of bitter cum on my tongue. I heard a grunt from the other side of the wall and the whole cock thrust forward into me and a stream of cum filled my mouth. I was not quite ready for the amount of liquid that came out, and my cheeks bulged, along with my eyes. My throat closed quickly and I opened my mouth wide and I know a lot of cum flowed out.
“Ooh, Frank! You shoot quite a lot! It actually spurted out of Mike’s mouth! Mmm! Mmm!” I could feel her now licking my chin. Meanwhile, more spurts of cum were firing from the cock in my mouth.
From my “cum games” with Jane, I knew that I was not bothered by it, so I began to swallow the copious amounts of fluid down my throat. As Frank’s cock was softening, I felt Jane unlocking the handcuffs and I reached up and fondled his balls and ran my hand along the length of his cock, and I squeezed out more fluid. Jane also untied the blindfold from me. I blinked as my eyes adjusted to the light.
Frank’s cock was now quite a bit softer. His cock was a dark pink color, with an even darker pink head. A bit of liquid was clinging to the slit in the end, and there were white globs of cum in various places along the shaft. I looked at Jane who was grinning from ear to ear. She grabbed Frank’s now soft cock and she kissed it, and again I felt her hand behind my head, now pulling me to a kiss that met right at the head of Frank’s dick. We kissed and slobbered over it, cleaning the cum from it, and she was cleaning the cum from my mouth.
“See what happens when you can’t hold your liquor!” she said to me.
I reached behind her head and pulled her into a kiss. Our tongues lashed at one another, tasting and licking up Frank’s cum.
As his dick disappeared through the whole, she looked at me.
“Are you angry?” she asked.
“No,” I replied, “things with you are always an adventure!”
“Did you enjoy it?”
“Well,” I thought, at first unsure, “yes, I did. I don’t think I’d have let you talk me into this without the blindfold and all, but now that we’ve done it, yeah, I did.”
She was smiling at me again.
“Want to do another? I want to watch again, but this time, I want to see it with your hands free and have you look in my eyes!”
This time I knocked on the wall.
A rather modest looking cock came through the hole. It was still rather flaccid and Jane leaned in and kissed it on the uncut head.
“Together!” she said to me, and we both leaned together and kissed it and it began to grow. I opened my mouth and took the head in, and she leaned a bit further and licked his balls. It grew some more from this and was now growing to quite a respectable length and girth. As it grew, the head began to protrude through the foreskin a bit, and I grabbed it with my hand and pulled back, exposing the pinkish, purplish head. I tapped Jane and she looked and I fed the now hard cock into her mouth. She bobbed her head on it for a few seconds, then slowly withdrew it from the warm confines of her mouth and turned it toward me. I smiled as she pushed it my way, and I pursed my lips and let it push its way into my mouth.
“Damn, that is so sexy!” she said as I began to bob my head, and used my hands to pump his shaft.
We kept swapping from my mouth to hers and then back again. The guy on the other side of the wall began to moan, and then we heard him say, “I’m gonna cum!”
Jane pushed him into my mouth and I felt the first jerk forward and the warm fluid shoot from his cock. I slipped him from me and fed him to Jane, but another shot fired before he was in her mouth. A big glob hit her cheek and her hair and then she had him in her mouth again. I watched as he throbbed and emptied his balls into her. The throbbing subsided and I again took him in my mouth and sucked on and squeezed his cock, trying to get more. I let his limp dick slip out of my mouth and turned and kissed Jane. I licked the cum from her cheek and tried to get it out of her hair.
I looked down at her bare chest and could see more cum there and leaned in and licked it from her there, too. We were lost in our cum kissing bliss when our mystery man slipped two twenties through the hole.
“Thanks, that was terrific!” he said.
I just looked a Jane.
“You take them!” she said to me, “a bonus for the first timer!”
Before Jane could ask again, I knocked on the wall and a new dick snaked through the hole. This was the biggest one I’d seen in person, by far. It was only about half hard but it was clearly bigger than mine, and I’d been told that I should be proud! I leaned in and opened wide and took the head in my mouth. I ran my tongue around it and it started to swell even more. I sat up high and pushed my head forward as the dick’s owner pushed forward and it hit the back of my throat, causing me to gag. As I coughed and pulled my head back, Jane laughed and looked at me. She grabbed the prick and pumped it several times causing it to swell to be fully hard. She looked at me and opened her mouth and pushed her face forward. I could see that she had enough in that he must have been hitting the back of her throat, but instead of gagging, she breathed in and then pushed her head forward and kept taking him into her mouth until her nose was at his thick tangle of black pubic hairs. She then withdrew again.
“How do you do that?” I asked her.
“Practice!” she said, gleefully. “I’ll teach you, and you can do it, too, but not today! Here, take as much in as you can, just use your tongue for what’s inside, and your hands for the rest!”
She pushed the cock back toward me and I did as she suggested. Even without trying to take in too much, the head felt huge in my mouth. I ran my tongue all around the head, pulled the big cock out, and then ran my tongue up and down the frenulum causing the man to moan. I was jacking his shaft with one hand and caressing his balls with the other. I opened wide again and took the head into my mouth again and he started to rock his hips, fucking my mouth with his monstrous dick.
“Mmm, I’m gonna cum!” came the voice from the other side of the wall. His hips jerked forward again and he began to flood my mouth with his semen. Although he was less of a “shooter” than the previous two, he seemed to produce an enormous volume of cum. I was swallowing to keep up, but still some spilled from my lips. I kept the suction going until his posture began to relax. He was not nearly as hard as he was even moments ago, but still bigger than me. I squeezed the massive shaft with my hands and purposely made a slurping sucking sound as I tried to get the last bit of cum from him.
I looked over at Jane and she was grinning from ear to ear.
“That was awesomely sexy!” she exclaimed as she moved in to kiss me and share in the taste. As we kissed, the dick withdrew and a fifty flopped in through the hole.
“I guess he liked it!” Jane said.
All in all, Jane and I blew five dicks that night. She pulled out a tub of wipes from her large purse and we cleaned each other up before heading to her car.
“Well, would you do it again?” she asked.
“Hell, yeah!” I replied.
“You better still have time to fuck me!” she said.
“Double hell yeah, to that!” I replied, “but I discovered something about myself! There is something entirely empowering about sucking off a cock! I always thought that it was kind of demeaning, but I realized how much it is empowering! I could deny it, or I can deliver it!”
“Come here!” she said to me as we stopped for a light, and kissed me. “I think I’ve created a monster!”
“Do you think that Frank would participate in a real three-way – with no wall in between?” I asked.
“Oh, baby, I have created a monster! And yes, I’m sure I could convince Frank to join us! He likes to suck cocks, too, so it’ll be a great time – especially for me!”
We went back to my place and as soon as we entered, she was unbuckling my pants and stripping me out of my clothes.
“On the bed!” she commanded, and I did as I was told.
She did a strip for me – not exactly a strip tease, because it was way too direct to call it a tease. She was soon naked and pounced on me, turning herself around so we were in an immediate 69 position. She sank her wet pussy in my face and leaned down and took my cock in her mouth. After a few minutes of that, she sat up and ground herself over my face.
“Eat me up, Mike!” she said.
Her hips bucking on my face, she reached her first orgasm, nearly drenching me in her fluids.
She turned and kissed me, licking my face, and simultaneously impaling herself on my stiff cock. She bounced on me, more fucking me than me fucking her. After all the stimulation of the night, I was quickly unleashing a torrent of semen into her, and I knew what was coming next.
“Now, clean me up, you dirty boy!” she said as she hopped off of me, and moved herself up, and pushed her pussy over my mouth. My cum was slipping from her lips and down onto my face. I opened my mouth and used my tongue to gather as much of my white, runny, slimy cum from her cunt as I could. She soon reached another orgasm, bucking her hips into my face.
After that, she kissed me again, and we both settled down and fell asleep.
About a week later, I got a call from Jane.
“Frank is on board – come to my place tonight – about 8:30!”
As quickly as that, she hung up.
All afternoon I was a mixture of excited anticipation and a bit of “what the hell have I gotten myself into”. The night at the glory hole had awakened desires in me that I did not know that I had, but it had been somewhat anonymous. I knew that it was Frank, but I’d never met him, and never saw him.
I got to Jane’s place and she let me in. Frank was not there yet, but Jane pulled me into a kiss.
“I’m SO excited for this!” she said to me. “Are you, too? Please tell me you are!”
“I am,” I said, “but a little nervous, too!”
“About what? I’m here with you – and you’ve already eaten more than one of Frank’s loads – out of me, and direct from him! He can’t wait to meet you – he’ll suck your cock, too!”
That did have me a bit excited.
The doorbell rang, and Jane pulled me along with her to answer the door. Two very handsome guys were there – I was only expecting one, but Jane seemed to know what was going on.
“Frank! Ed! Please come in! Guys, this is Mike, Mike this is Frank and Ed.”
I looked at her questioningly, but she just smiled. Jane. Always something up her sleeve, and she hadn’t let me down yet, so I decided to just go along with her.
“Frank,” I said, to the shorter of the two. Shorter than me, he had a rugged look about him. Sandy blonde hair, deep blue eyes and an easy smile. Frank was holding a bag with a couple of bottles in it.
“Ed,” I said to the taller one. He was a surfer dude type, with shaggy red hair, slim, yet muscular.
“Nice to meet you, Mike, formally, at least!” said Frank giving me a familiar look.
“So, Mike,” Jane began, “when I mentioned this to Frank, Ed was there and wanted to join us – I KNOW that you won’t mind at all! Come on everyone, a drink is in order!”
I was reminded that drinking with Jane was how I got to this fork in the road in the first place, and I told myself to go easy.
Frank gave Jane the bag, holding a couple of bottles of nice Scotch and she poured four shots.
“First one down quick!” she declared and we each took a shot. She then poured a generous amount in each of four glasses and we went to the living room. I sat on the couch, and Frank quickly sat with me, while Jane and Ed each sat in stuffed chairs.
Frank wasted no time.
“So Mike, Jane tells me that the other night at the glory hole was your first time. You did pretty well for a first timer! She also told me that you stayed for more! It must not have been your first time to taste cum, though?”
I looked at Jane, she just smiled back at me, and replied, “No, not even the first time for yours, Frank! About a week before that – remember hooking up? I brought your load home to him and he happily sucked it out of me – right where you deposited it!”
“Damn, that’s hot!” Ed interjected.
“I take it you’ve tasted your own, too?”
“Yes, I have,” I replied.
“Lots of times,” Jane jumped in. “Out of my pussy, off my tits, off my ass, nice gooey cum kisses!”
“I’d like to see that!” Ed said.
“Or join in!” said Frank.
“Oh, I have lots of ideas,” said Jane. “Starting with this!”
She stood up, and grabbed a deck of cards, fanning them out to the three of us.
“Low card loses an article of clothing.”
“What about you?” Ed asked.
“Hmm, I’m in charge,” she replied, “I’ll direct, and then maybe lose a piece or two as I see fit!”
I drew a deuce, and kicked off my shoes without even waiting for the others. As it turned out, Ed also drew a deuce, and did the same.
After a few rounds, we were all shirtless. I still had my jeans on, Frank and Ed were both down to their underwear – Ed’s a pair of dark blue briefs, his 3/4 stiff cock outlined nicely and off to the side somewhat, and Frank’s a pair of loose boxers with a definite tent rising. Somewhere along the way, Jane was down to a lacy bra and matching lace panties.
I lost the next two rounds – first down to my own boxers, and then again, so it was time to lose them. I hooked my thumbs in the waistband and pulled the elastic out and over my own stiff cock, and pushed them down over my hips.
“We have a winner!” Jane said, “or, I suppose, a loser!”
“Mike, your reward for losing, is that you get to remove everyone else’s underwear, you get to choose the order.”
“Including yours?” I asked.
She glanced at the lacy material covering her pussy. She ran her hand down over her mound and remarked, “They are very wet, and I think they need to come off, too!”
I looked at everyone, trying to decide the order. I’d seen all of the genitalia in the room except for Ed’s, so I decided to leave him for last. I walked over to Jane first, and kissed her, running my hands over her bra-clad breasts, and down over her belly. I moved my hands to her hips, and then caressed her round, beautiful ass. I squeezed and gently smacked it, holding the smack against her. I ran my hands up her back and found the bra clasp and deftly unhooked it. I took the straps and slid them over her shoulder and down her arms, exposing her smallish, but very perky tits. I leaned down and kissed each nipple, running my hands along, too, caressing each one in turn. I then ran my hands down her sides, and I hooked my thumbs in the waistband of her panties, and as I moved them over her hips, I sank to my knees and kissed her pubic mound, and slid my tongue over her exposed clitoris.
“Mmm!” she moaned.
I pushed the panties down to her feet and she stepped out of them. I stood again, brushing my hard cock against her pubic region as I turned to walk to Frank.
As I got to him, I had a decision to make – do I repeat everything I did with Jane, or do something different? I decided to go boldly where I’d never been before, and I walked up to him and kissed him, too, running my hands over his chest, and down over his stomach, too. I moved my hands around and caressed his ass, too, and gently smacked it. This was, obviously a more masculine ass than Jane’s with a muscular firmness to it. I hooked my thumbs in his waistband. As I sank down, I kissed each of his nipples, too, and ran my tongue around them. I sank to my knees as I lowered his shorts. His stiff cock was bobbing in front of my face, and I kissed the head of it. I opened my mouth and let the head slip between my lips. As my hands pushed the boxers to his feet, he stepped out of them, and I ran my hands back up his legs and again caressed his ass, and now his balls. He moaned and rocked his hips forward, pushing his cock further into my mouth.
I quickly stood and let him slip out of my mouth. I reached behind his head and pulled him into another kiss.
“Patience!” I said to him, “I still have another package to unwrap!”
I turned toward Ed. I looked at the outline of his hard cock under his briefs. It was clear to me that Ed was the winner of the largest cock in the room. I walked up to him and put my hand behind his head and pulled him into a kiss. He was slightly taller than me, so I had to pull him down to me – I was used to being taller than most, so this felt unusual to me, but nonetheless, it felt right. Ed kissed me back, and I felt his tongue brush my lips. His lips were softer than Frank’s, but not as soft as Jane’s. I ran my hands along his chest, too. He was more “defined” than Frank, but in an athletic way, not a body-builder way. I leaned down and kissed and licked his nipples as I had with the others. I ran my hands over his belly and around to his ass, which was firmer and tighter than the other two. I hooked my thumbs in his waistband and pulled the elastic out and over the head of his stiff cock, and then slid them down past his hips. As with the others, I sank to my knees as I pushed his underwear to the floor. I looked at the head of his cock, now shiny with precum and I kissed and licked it – slippery with his liquid. He was both longer and thicker than Frank. The scent of his cock, musky and manly turned me on in ways I did not previously know. He rocked forward and pushed himself into my mouth even further. I did my best, but could not take him in, and started to choke in the girth. I let him slip from my mouth and coughed.
When I recovered a bit, Jane was leading Frank over to where Ed stood. She pushed the two of them together until their cocks were touching, and started to frot them together.
“Mike, you need to take over for me!” she said, inviting me to grab the two cocks together.
I gently took the two cocks in my two hands and began to pump them up and down. Ed and Frank began to lean in to one another. Both cocks were oozing clear precum that I pumped onto their shafts. Frank’s skin was a bit darker than Ed’s, and his head was more purple color, where Ed’s was more pink. I leaned down and licked the heads together from one to the other.
“Holy hell, that’s hot!” Jane said. Her hand had drifted down my back and was rubbing over my ass and to my balls, but I was focused on the two beautiful pieces of meat in front of me. I leaned down again and opened my mouth as wide as I could and tried to force both into my gaping mouth. It really stretched me to the point of pain, so I contented myself by licking the two heads.
Ed looked down and saw what I was trying and he said to Frank, “Let’s rock in opposite pattern!”
At first Frank didn’t understand, but Ed held Frank while he pushed his cock forward, and then as he withdrew, he nudged Frank to push forward. Soon the two cocks were pistoning forward and back so that one was always pushing into my mouth. I opened wide again to help accommodate them, and tried my best to keep breathing through my nose. The guys were rocking their hips and I kept getting a cock head slipping between my lips.
“God, I’m gonna cum!” announced Ed.
“Yeah, Ed, cum in his mouth!” Jane shouted.
Frank just grunted and both guy’s hips started thrusting forward, not in the smooth motion from before, but in a jerky, “I’m about to cum!” motion.
Ed’s hips pushed forward and a stream of white liquid fired from the head of his cock. A bit went straight into my mouth, a bit more on my face and a lot shot Frank and his cock. Another jerk of his hips and I wrapped my lips around his cock and he fired right into my mouth. I swallowed quickly getting ready for another when I felt Frank’s hips spasm forward, and felt his cum hit the side of my face. I opened as Ed again shot a rope, this time mostly in my mouth, but also on my face. I pulled back from Ed’s cock and turned and took Frank in my mouth. His cock was white and sloppy with cum, some from Ed, and some his own. He spurted another stream directly in my mouth, which I also swallowed quickly, as I tried to run my tongue over his shaft and suck the cum off of him.
Ed had reached down and was jerking and squeezing his cock as more, less intense spasms of cum were still oozing and dribbling from it. He rubbed the cum on my face and I let go of Frank’s cock and turned again and took Ed in my mouth. I grabbed his shaft with my hand and squeezed as my mouth sucked hard to extract those last dribbles from him. I let his soft cock slip out again, and did the same for Frank.
“Damn that was hotter than hell!” Jane said, as she pushed her face between Frank and Ed and started to kiss and lick my face. “You’re all covered in their spunk and I want to lick it all up! Let’s clean up these cocks together!”
She was alternately licking my face, and sucking on the soft cocks in front of her, trying to clean up the cum. And there was a lot of cum to clean! Eventually, Ed pulled away, only to push his face in with Jane and the three of us were kissing and cleaning up Frank. Then Frank joined us, and the three of them were licking my face and neck.
“I think Mike needs some proper attention!” declared Jane, as her hand was rubbing my still stiff cock, “but we need to move this show to the bedroom.”
We went to her room and collapsed on her extra large king bed. I was pushed onto my back and immediately Frank and Ed moved to kiss my cock. Someone pushed my legs out wide and while one started bobbing his head on my cock, the other was licking my balls. Then I felt a tongue at my back door and I froze, not sure if I was ready for that, or not.
Jane felt me tense up and moved up to kiss me.
“I think you’ll love it!” she said, “but if you are not ready, we can skip it – for now!”
I was still feeling a tongue on my ass, and my cock was enveloped by a warm, wet mouth. I felt myself torn. She’d been right all along with opening me up to new sexual adventures, but this was really a new step.
I didn’t have to say anything, she read my face.
“Ed,” she said, “not yet! But I have an idea! Come up here and fuck me while Mike is eating my pussy!”
I looked at her with a raised eyebrow.
“You just had his cock in your mouth, this way you get the best of both worlds!”
I smiled at her and she quickly moved to push her pussy right over my mouth. Frank continued to suck on my cock, and now Jane also pushed her face into my crotch. She and Frank kissed each other and then began to lick my cock like they were sharing a Popsicle.
I started to nibble on Jane’s clit and I could feel Ed moving up the bed and then climbing in behind Jane. I looked up and saw his now again stiff cock and tried to imagine it pushing into my backside and thought how there’s no way I could handle it. Ed grabbed the shaft and began to rub it against Jane’s labia, splayed open just in front of my eyes. As he eased his hips forward, her lips opened to take him inside her. She moaned as he did and I closed my lips around her distended clit and ran my tongue over it. The low moan increased to an almost scream. As Ed pushed in further, I moved my head back a bit and ran my tongue now over his shaft and licked his balls. He smelled of manly musk and cum from before and the scent filled my nostrils and turned me on.
“This is such a fucking sexy view!” I said as I watched Ed start to push in and out of Jane’s pussy.
“Mmm, I can make it even better!” Jane said.
“Go on Frank – do it!”
Again I felt the mattress moving and Jane again lowered her head and took my cock in. As I looked up, Frank came in behind Ed and started to rub his hard cock against Ed’s butt. He leaned down and kissed Ed’s butt cheeks and ran his tongue down over his puckered hole, and began to push into it with a finger. He put a generous glob of lube between Ed’s cheeks and started to rub his finger in and out of Ed’s ass, then slipped his finger out and pushed the head of his cock against the opening.
“Oh, Frank, fuck me!” Ed moaned.
Ed was fucking Jane and Frank was fucking Ed and I was watching and licking while Jane was sucking my cock. Suddenly I felt her fingers now pushing into my own ass. Just barely a fingertip at first, then more and more. When she pushed her finger against my prostate I lost it.
“Oh God!” I screamed as I spurted out my own stream of semen. I felt her mouth clamp down on my cock and her finger push hard against my prostate. My hips bucked and tensed as I emptied myself in her mouth.
As I enjoyed the sensation of orgasm, I again looked at the scene right in front of my eyes. The two cocks were moving in and out of the orifices in front of me. I again began to focus attention on Jane’s clit while Ed began to move faster.
“Oh, Jesus!” Jane exclaimed, “I’m nearly there! Don’t stop – either one of you! Yes, yes, yes, make me cum! Oh God! Yes! YESSSSSSSSSS!” Her hips were spasming and her voice unintelligible, when Ed started.
“Damn! Your pussy is gripping me! I’m cumming, too! Frank you feel so good in my ass!”
He slammed his hips forward into Jane and I could see his shaft clenching and I knew that he was emptying himself deep inside her.
Suddenly Frank pulled himself free of Ed’s ass and started to jerk his cock, aiming it right at me.
“I’m cumming too! Take it Mike! Take it!”
A moment’s hesitation hit me as he had just pulled his cock from Ed’s ass, but Frank’s beautiful cock cumming again intrigued me and I opened my mouth and he leaned down so I just got the head in my mouth as the first dribble oozed from the slit in his head, followed by several strong shots that I eagerly swallowed. His dick tasted mostly of the lube – not great, but the cum was still pungent with his smell.
He backed his cock from my mouth, and Ed backed up just a bit and his soft cock slipped out of the folds of Jane’s pussy. It flopped down so I opened my mouth again to take him in. This cock tasted strongly of cum – Ed’s and Jane’s. Much better than the lube. I sucked on it and Ed’s legs again tightened and I could taste those last bits of cum. I licked all around, tasting Jane’s pussy all over his prick.
“Oh!” Jane said, “Here comes the leak!”
A river of mixed up cum came flowing from her lips. I tried to catch it, but it flowed out rather forcefully, and much of it went on my chin and down my neck. I pushed my head up and clamped my lips to hers, slurping and sucking the cum and vaginal juices from her.
“Goddamn!” Jane said, as she and Frank and Ed all moved themselves up and around. Once again they were licking and kissing my face and neck cleaning up what they could find. I kissed each of them and Jane settled half on, half off of me, with Frank cuddled just behind her, and Ed settling on my other side.
Exhausted, I fell asleep.
When I awoke, I felt Ed moving and getting up. I looked at him quizzically.
“I’m sorry, I have to go. It was wonderful, we absolutely must do this again sometime!”
He leaned over and kissed me. Jane sort of moved, but not really.
“Tell everyone I’m sorry to have to leave, but I must go!”
“Why?” I asked.
“My boyfriend doesn’t mind ‘extra’ activities, but we agree that we will sleep at home!”
I was a bit surprised to hear it, but it was not like I was going to complain.
“You were terrific,” Ed said to me. “He’s going to want to have you over for supper, but he’s strictly into guys, so no women allowed! Frank will give you my number if you are interested, give me a call, I’m sure that you and Thomas will hit it off!”
I looked at him for a second before responding.
“I’m sorry I was not ready for you – you know, for fucking. I’ve never done that and, well frankly, you’re a bit intimidating.”
“No worries – I understand. Give me and Thomas a call – he’s smaller than me, and smaller than you, too. We’ll gladly get you started, and we’ll be gentle and slow – until you beg us not to be!”
With that he winked at me, and headed into the living room to retrieve his clothes and go. His words were rattling around my brain as I fell back to sleep with Jane and Frank.
When I awoke again, it was to sensations that my sleep fogged brain was trying to place. As I opened my eyes I could see that Jane was kissing my neck and my face, planting a few pecks on my lips, too. But there was more. As the fog rolled back I realized that my morning wood was being encouraged by a warm mouth. I kissed Jane, and then looked down, confirming that Frank was trying to swallow my cock.
“Wakey, wakey!” Jane was saying between kisses.
“Mmm! A nice way to wake up in the morning!” I said.
Frank pulled my cock from his mouth, and grinned, “Oh, you were already ‘up’ – I was just taking advantage!”
With that he opened his mouth and again took me into it. His tongue was swirling around my head, and his hand was pumping the shaft. I put a hand behind Jane’s head and pulled her into a deeper kiss.
When she broke the kiss she looked right in my eyes, then leaned forward and whispered in my ear.
“I want to watch you fuck Frank! He wants it, too!”
I pulled back from her and looked at her face. She was smiling at me, and nodding her head just a little.
“You’ll love it! And so will he! He has a nice tight bum and your cock will fill it so perfectly!”
I thought about what Ed said as he left, and the things I’d done already that I had never thought I’d do, but I certainly did enjoy sucking cocks. I’d already fucked Jane’s ass before, too, so what would be the harm?
“Only if you are the one feeding me into him!” I said to her.
She squealed with excitement.
“Frank!” she said, “he’s up for it!”
Frank looked up at me, my cock filling his mouth, and smiled with his eyes. He pushed his head down until his nose was in my pubes, his throat gripping me, and then slowly backed up, his tongue bathing my entire length with his saliva. I involuntarily pushed my hips up toward his retreating mouth, but I slipped between his lips and was suddenly cooled by the wet sensation and the air. He crawled up to me and kissed me, his mouth smelling of my cock.
“Don’t be too gentle!” he said to me as he broke the kiss.
He turned around and went down on his forearms, his ass lifted in the air. His balls were dangling beneath his puckered opening. Immediately Jane pushed her face between his buns and ran her tongue over his backdoor. He moaned loudly.
I got up and moved to join her. I ran my hand over his taut buns, down his thighs, and back up again. I ran my hands over his balls, and grasped his stiff prick. I leaned in and kissed his buns now, and Jane turned slightly and kissed me and Frank’s ass. The shape of his ass was quite different from Jane’s – less rounded, more squared off. Even the shape of the opening seemed different – more vertical, and not as rounded. Jane put a hand on each of his buns and pushed outward, opening him up even more, and then it took the rounder shape. I leaned in and kissed right on the puckered opening. I’d rimmed women before, and got about what I expected – at first he was tightly closed, but as I probed with the tip of my tongue, he softened and opened. As I moved to kiss his buns again, Jane zeroed in and started her own rimming and he moaned again and began to open up more.
Jane began to drizzle some lube on the cleft above his ass hole and it dribbled down onto his opening. As it slid down further she caught the drips with her thumb and began to massage it around and into his hole. She held the bottle of lube toward me and put some in my hand, and then I, too, began to rub and massage him. As I took over the massaging part, she took some of the lube and coated my hard cock, slathering it good with the slippery, thick gel. I slipped a finger inside of Frank and again he moaned.
“More!” he said, “more fingers!”
I pulled my finger out, and inserted my forefinger and middle finger together.
“Oh yeah!” Frank said as I began to finger fuck him.
Jane had different ideas, though, and grabbed my hand and pulled back. My fingers slipped out of Frank, but his opening remained a bit gaped. She pulled me, cock first, toward his bum hole and started to push my cock into him. It was a very tight fit, and at first, I did not think it was going to work at all, but she patiently keep pushing me in, and then pulling me out until on one of the pushes, my head slipped right inside him, eliciting the biggest moan yet from Frank’s throat.
Jane did not push further, but also did not pull me out, instead letting me sit just there, barely inside of his butt. After about 20 seconds, I felt Frank pushing back toward me, and Jane pushed on my ass, urging me to go further. Frank’s ass seemed to open up and invite me in, and I was soon about 1/2 way inside.
“Damn, you’re big!” Frank said, “give me a second to adjust!”
We held still again until I sensed Frank again pushing his ass back at me.
“Take me!” he said, “I want all of you in me!”
I leaned forward again and slowly slid into him until his taut buns were pressed against me. I rotated my hips a little against his ass and a guttural groan was all I got in response. I slowly began to pull out, and then push back in. I could feel my balls slap against his perineum.
“How’s it feel?” Jane asked.
We both answered.
“Amazing!” I said.
“So goddamned full!” Frank said. “Fuck me hard, Mike! God, this feels so good!”
I picked up my pace until I felt like I was slamming into him with every forward thrust. The sound of “slap, slap, slap” and Frank’s moans were filling the room and I hit the point where nothing was going to stop me from cumming.
“Oh, shit! I’m gonna cum Frank!” I said, and I started to pull back.
“No!” he shouted, “I want it in me! Cum in me! Fill me up, please! I’m…I’m…cumming, too!”
I wasn’t sure how that could happen, but my mind had lost all ability to reason and I slammed into him again, feeling my balls contract and his ass gripping me as I unleashed my load. The orgasmic release felt glorious and I felt spurt after spurt going deep inside of him. My hips were thrusting against his ass, and my hands were gripping his hips, his ass gripping my cock.
As my orgasm subsided, my strength was suddenly gone and I directed Frank to lay down on his side as I tried to keep my cock inside him and lay down, too.
“Damn, that was fucking awesome!” Jane said, “Just look at how much cum you shot, Frank!”
“I’m sorry, I messed your sheets!” he was saying.
She ran her fingers through the white mess and licked off the rewards.
“Mmm, totally worth it!” she exclaimed.
She reached around and caressed my balls.
“Did you empty these inside him?” she asked.
“Yes, I did!” I replied, as my now softened cock was pushed out of his bum.
As I slid out, so did a river of white cum and lube, also “messing” the sheets.
“Oh, wow, you really did!” Jane said, watching Frank’s ass leak.
Frank rolled over toward me and kissed me.
“Thank you!” he said.
“Oh, thank you!” I replied. “I didn’t know that it might make you cum, too!”
“You never had a prostate orgasm?” he asked.
“No,” I replied, “I guess not.”
“Well,” he replied, kissing me again, “that’s something we will have to fix, sometime!”
“Yeah, ‘sometime'” Jane said, “but not now – I have to get cleaned up and get to work, so we are going to have to take a raincheck on that. But, believe me, I’d love to be there!”
We all pitched in getting things cleaned up. Jane ran for a shower and Frank and I helped by stripping the bed. I was watching him move about the room naked, and felt oddly turned on by the whole thing. Six weeks earlier, I’d have never imagined the things I’d seen and done turning me on, but here I was, far the wiser for having met Jane, and tried her experiments, and lost that bet. A whole new world was out there waiting for me to discover it!