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.