Losing a Bet Pt. 02

This is (as the name implies) a continuation of "Losing a bet", a story that involves males engaging in sex together. As usual, if this is not to your liking, please move on to a different story.

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After the tryst with Jane and Frank and Ed, Ed's parting words kept rolling around in my head. I'd certainly enjoyed the many things that Jane had led me to, including fucking Frank's ass, and all the cock sucking, but the invitation from Ed would be without Jane. Somehow her presence almost felt like permission to explore my bisexual side, but if I took Ed up on his invitation it would be he and his boyfriend Thomas, and me, and as he said "no women allowed!" I was both intrigued at the thought of being with them, and almost scared to take that step away from having someone female there, too. Would that make me gay? Was I gay? I didn't really think so, but the emotions were making me kind of unsure.

About a week or so after our get together my phone buzzed. It was a text from an unknown number that read:

"Hi Mike, this is Ed - we met the other night, I'm a friend of Jane and Frank's. I'm just wondering if you've thought about my invitation. Thomas wants to meet you. We could have dinner at our place on Friday. BTW, I got your number from Jane, I hope you don't mind! :)"

I had been thinking about getting Ed's number, but I'd chickened out of asking for it, and now he'd made it a moot point. It did not settle my mind about things, though, so I decided that I should talk to Jane, and I invited her out for a drink.

"A drink, huh?" she replied. "So I can get you drunk and fuck you again?"

"Well, really I want to talk," I replied. "But fucking with you is always a good prospect, too!"

"Wow, just what a girl hopes to hear!" she laughed. "OK, a drink and a talk, then we can see what happens! Where shall we go? There's Gregory's near your place?"

"How about you come to my place, or me to yours? I don't want any prying ears."

"Wow, OK, I'll come by your place. This sounds serious."

"Well, a little, but mostly just private. I'll order some Chinese, too, so we can eat."

"Alright, I'll be there at 7-ish!"

She was at my place by a little after 7:00, and the food arrived just after she did. We sat down to eat.

"So what the heck is up?" she asked.

"Well, Ed invited me to his place to, um, 'meet' his boyfriend, Thomas, and to, well, I guess to hook up."

I was not quite ready to tell her that he wanted Thomas to fuck my ass, mostly because I was a mix of wanting it to happen, and fully frightened of it.

"Yeah, so?" she replied, completely unfazed by it.

"Well, I, uh, I," I stuttered, "I'm kind of not sure about it. In all of my previous times with guys, you've been there, so I've felt like maybe I'm still, uh, well,..."

"What? Spit it out, man!" she said.

"Look, if you are there, then it's still just 'bisexual', but if you aren't, am I... well, am I gay?"

"What?!?" she said, "Well, first of all, who the hell cares? Do you give a shit what some stick-up-their-ass society person thinks? I've had sex with just other women, does that make me a lesbian? I've also fucked you several times, so I must be 'just' a heterosexual! Who gives a fuck? Did you like being with Ed? Then go! When you're done, call me, and I'll come by and fuck you back into being straight if you need that to feel better about yourself!"

By that last comment she started laughing at me.

"You're really something, aren't you? Just go with it all! It's just fucking! Explore the whole person that you are! God, you simp, just go enjoy yourself. Or, don't go if you're not ready to take the step, but for God's sake, don't stay away because of what society labels as 'gay' or 'straight' or 'perverted' or whatever! It's consenting adults - either consent or don't!"

She sat there looking at me. I heard what she said, but here I was considering letting a guy put his cock in me. I was still waffling about it.

Suddenly she sat up, reading the look on my face.

"Ooh, I get it now! You're nervous from the other night! He was ready to take your ass. But you're an anal virgin, so will you let him fuck you? He's pretty big - maybe Thomas, he's not as big as Ed - probably not as big as Frank, either. Hey, you could practice deep throating, too!"

I just looked at her, and she could see that I was still confused and worried.

"Look, Mike, I can tell you are thinking about it, right? Most of us wonder what it's like for the 'other side' - girls think about what it would be like to have a dick and fuck someone - that's why we have strap-ons and dildos, and guys think about what it would be like to get fucked, only for you it's a lot easier - you already have two of the three orifices that us ladies have, so you can try it out! You've already gotten practice sucking cocks, so you should try anal play, too! Have you ever tried it, other than me putting my finger back there the other night? You've got a whole other world of play and pleasure just waiting for you to try! And you know what? If you'll let go of your society-fed neuroses, I know that you'll love it! I have experienced it, and I love it, and I don't have a prostate. Frank tells me it's heavenly cumming with a dick pushing on it. You sure made him cum a ton when you were fucking him, and you shot off like a fire hose as soon as I pushed on yours!"

I just sat there looking at her. What she was saying made sense to me, cognitively, but for some reason I was still apprehensive.

"Come on," she said to me, standing up and taking my hand, "we're going to my place, and I'm going to show you some things, and then I bet you'll call up Ed and say 'Yes, please!'"

She was pulling me along firmly, and I knew that "no" was not an answer to be attempted with her.

"Why do we have to go to your place for this?" I asked.

"Because, I did not pack a 'travel bag' with proper toys and such!" she replied, pulling me through the door.

On the way over I my stomach was full of butterflies, and my my head kept thinking about my sphincter. I wanted this, and I knew it, but I was still a bundle of nerves.

When we got to her place, she led me to her bedroom and told me to strip and lay down on the bed.

"Really, no drink first?" I asked.

"No - sober. You want this and you need to be fully sensitive and aware. And Mike?"

"Yeah?"

"Your going to love it, I promise!"

I did as she asked, and she went to her closet and started to open a couple of boxes. Onto the bed she placed a butt plug, a set of anal beads, and a fairly thin pink dildo, about 10 cm long, and she started undressing. When she was naked, she pulled out a pair of black, stretchy underwear and the biggest dildo I'd ever seen in real life. She pushed the dildo through an opening in the underwear and pulled them on, leaving her looking like a transsexual with a really huge dick. She turned to me.

"So, big boy, are you ready for this?" she asked, walking slowly my way, the big dong swaying with each step.

"There's no way!" I exclaimed, "I didn't think I could take Ed, and that thing is way bigger than him - bigger than anyone I've seen!"

She started laughing.

"You should see your face right now!" she said. "I'm not really going to try you with this! I do have one girlfriend who likes it, but she's had four children and says she needs something this big just to feel like she's being fucked! Anyway, no, this was just to get a reaction - and boy, did it ever!"

"Jeez, Jane, I'm really nervous here, and this is not helping!"

"I know, I just had to do it, but relax, see the things on the bed? They're all fairly small and will get you started and, again, I promise you are going to love it! Pegging - that's what it's called if I fuck you with a strap-on - that comes later, after you beg me to do it! Even then, I promise to start you with something more realistic in size than this monster!"

She slipped back out of the underwear and walked over to the bed. She crawled up to me and started kissing me, and running her hands over my chest.

"The first thing is to get you to relax, and get you into the proper mood."

Jane and I had fucked many times before, so there was a familiarity and an excitement in this. She never failed to turn me on. After some time of kissing and petting, I was as hard as a rock and had almost forgotten the reason we were there when she told me to roll onto my belly. When I did, she began to kiss and caress my butt. She pushed my legs apart a bit and took a position between them, on her knees and she bent down and gave her full attention to my backside. She kissed my buns and ran her tongue down each side, down to my upper thighs and then back. She came close to my hole, but never quite got there. Her hands were firmly kneading my buns, squeezing and pushing them up, and a bit open. When her thumbs brushed over my anal opening it gave me a jolt. She pushed me open again and then put a kiss directly on that puckered entrance. I moaned loudly, enjoying the warm sensation.

She continued to kiss me directly on my back door, then I felt a finger pushing. She was then sucking loudly on her fingers, and then she began to push into me with her finger. I tensed and clenched my ass.

"Relax, baby," she said to me. "The key is relaxing - keep it all sensual, and remember to enjoy the sensations!"

She again kissed me - my buns, my thighs, my butt hole. She ran her finger down the cleft of my buns, and then pushed when the finger got to my opening. I closed my eyes and tried to just let go. She pushed inward, and then stopped, then she repeated. With each inward push, the pushes got stronger and more insistent until I could feel the fingertip slipping inside me. She pushed a bit further, and then withdrew, only to keep coming back, pushing in a bit further each time. Finally she pushed in and kept pushing.

The feeling inside me was glorious! She started pumping her finger in and out, and rubbing the prostate as she went. Each touch sent shocks through me. Then she slowly pulled completely out of me, and left me feeling empty.

As I looked around, she had grabbed a bottle of lube with a pump top.

"This may be a little cold, at first!" she said, pressing down on the spout and a thick, clear gel landed between my cheeks. I jumped a little - she was right, it was kind of cold! But, as soon as it landed she began rubbing it down and over my bum hole, and pushing it into my bum. Another glob landed and she was pushing it into me as well. Then, once again, her hand was gone, and again I looked back.

She had picked up the pink dildo and was spreading lube on it.

"See?" she said, "not much bigger than my finger - smaller than two together."

She grabbed the dildo near one end, and pointed the end right at my asshole. I felt it push against me, and expected to be somewhat resistant to it, but my butt was used to her finger, so this slipped in fairly easily. She was slowly pushing it inside me. It was an odd sensation to me. I could feel the tip sliding its way into me, and the width of the dildo holding me open. She began to move the dildo in and out, slowly, at first, then picking up speed. After a few minutes, though, she slipped it completely out of me. I audibly gasped at its absence.

"Don't worry!" she said smiling, "I'm not going to leave you empty for long!"

Very quickly I felt another push at my anus. It pushed in, and I could feel my butt close around it, and just as quickly felt another push. This must be the anal beads, I thought to myself as it, too, pushed its way past the sphincter, which again closed around it. Then another. Each one was a little larger than the last, and she kept pushing until I felt five balls enter, with another stretching me even more than the previous ones. Somehow I was pushing against this one and again she spoke to me.

"Relax your muscles! Just enjoy the sensation! The others all feel good, right? Especially once they slip past the gate!"

She was pushing and relaxing the last bead (at least, I hoped it was the last one!) and with each successive push I opened wider, until it almost popped going in. I felt my butt relax again, and close around the latest ball.

"Oh my God!" I moaned.

Jane giggled and began twisting the toy in my ass, and pulling it against my hole, and then pushing it in again. The sensation of the length of the toy on my insides was something unknown to me, and I was really getting into it.

"Are you ready to go to the moon?" she asked me.

I couldn't imagine what she was talking about, but said, "Oh, yes!"

Suddenly the toy started to vibrate in my ass.

"Holy shit!" I exclaimed involuntarily.

Between the buzzing in my ass and her pulling and pushing suddenly my cock began to spew out cum. Not in blasts like I was used to, but in an almost continuous stream like from a hose. My mind was completely overwhelmed with the orgasm and I lost all conscious thought processes.

When I could think again, I spoke.

"Jane... too much... oh my God... switch it off!"

My hips were twitching and I could not focus on anything.

She did finally switch it off and I again got some control of my faculties.

"That was amazing! Absolutely amazing!"

I slumped down on the bed, my belly and dick settling into a massive pool of cum.

"Oh, God, I made a huge mess!" I said, sitting back up.

Jane reached down and ran her fingers through the pool of cum on the sheets. She did her best to scoop up some of it, and pushed her fingers into my mouth, and I slurped and sucked them clean. She repeated the motion, and also ran her fingers over my belly, collecting the slimy liquid and feeding it to me. She then pushed me onto my belly again, and I felt a tug in my ass as she grabbed the loop at the end of the beads and put a slow but steady outward pressure on the toy still buried in my ass.

I moaned as my butthole expanded and allowed the last bead in to go out again. I felt myself close down again as it slipped out, and the toy again tapered down. She kept up the pressure and slowly the next one slipped out, and then the next, and quickly the smallest bead popped out. My ass felt very empty, and I could tell that it was still gaping open. Jane slipped a finger, then two into me again, pressing down on my prostate. Again I moaned.

As she pulled them out again, I felt a cold sensation replace her fingers. She kept pushing and rotating something new against my sphincter and it again opened. Similar to the beads, once the breadth of it passed, my asshole closed down. I felt her twist things around a bit, and push on it so it, too, pressed against my prostate.

"There!" she said, in a self satisfactory voice.

"There, what?" I asked.

"A pretty butt plug for you!"

I heard her scramble and the "click" sound of her phone snapping a picture.

"See?" she said, showing me.

There, between my butt cheeks was a green emerald-like jewel. My ass again felt pretty full.

"A butt plug?" I asked.

"Yes, you should try walking around with it inserted. It'll help you get used to having something up there - and when you join Ed and Thomas, you'll be ready for them!"

"What about when I have to poop?" I asked.

"Obviously, you take it out, take a shit, clean it up, and then put it back! I'll give you a tube of anal lube, too!"

"Anal lube?" I asked.

"Yes, it's a bit thicker than standard lube - you'll appreciate that! Now, I need to get to bed early, I have to be out early in the morning. You want to stay? You can, but no more sex tonight! You want to shower?"

"With the butt plug?" I asked.

"Of course! It can get wet!"

I went to take a shower. The sensation of that thing up my ass was strange to say the least, but I got used to it - well, a little bit, anyway.

Jane was up and about by 5:30 the next morning, and I was awake by six.

"Promise me that you'll keep that plug in all day!" she said as she left for work. "Just pull the door shut on your way out!"

I got up and grabbed some coffee and quickly made my way home to change and get to work. I promised I'd keep the butt plug in, so I did. Going to work that way had me distracted and horny all day long. By mid afternoon, I was sending Ed a text.

"Hi Ed. What can I bring on Friday for dinner? Wine? Dessert?"

By now I'd lost all focus on work. My butt was full with the plug, my cock was at least half-hard all day, and now I could do nothing but wait anxiously for a reply.

"Hi Mike, it's great to hear from you! Just bring yourself, Thomas and I will provide everything we need! Come by around 7:00" At the end of the text were three emoji penises.

I looked at the clock, it was only 3:15, but I needed to get out of there. I told my boss that something had come up and I needed to get going early. He had no problem with it, and I raced home.

I put a towel on the bed and stripped out of my clothes. I sat on the bed, my legs splayed open and I reached between them and began to push and pull on the butt plug. As I pushed it in, I experimented with the pressure direction until I found one that pushed my prostate explicitly. My dick was hard and pointed at me and with my other hand I started to jack my cock. I thought about some "self facial" videos I'd seen and I threw my legs up and over and found myself looking right up at the head of my own dick. Reaching the butt plug was a bit awkward now, so I just started to jerk off furiously. I felt my balls contract and I opened my mouth and tried to direct my orgasm into it. Mostly I failed at that, shooting my cum on my forehead, and my neck and my chest as my hips jerked with the climax. As my hip twitches settled down, though, I succeeded in directing the flow into my own mouth. The pungent taste was a total turn on to me now, and I played with it on my tongue before swallowing it down. As I settled down, I squeezed the last bit from my soft cock, and gathered it on my finger and licked my finger clean. I wiped it from my forehead and my neck, also enjoying that.

I took a nice shower and ate some dinner.

Then I called Jane.

"Well," I said, "I'm invited for dinner on Friday!"

"I knew you'd go!" she said. "I want to hear all the details on Saturday - and I do mean all of them!"

"Should I wear the plug when I go?" I asked.

"Oh hell yes!" she replied, "Why is that even a question?"

For the next two days I was in a constant state of arousal with the butt plug in place, and the anticipation of spending the evening with Ed and Thomas.

I showed up at their apartment on Friday with a bottle of scotch, even though I was told it was not necessary.

"Really, you didn't need to!" Ed said as I was let in the door.

"Mike, I'd like you to meet Thomas. Thomas, this is Mike!"

I reached out to shake Thomas's hand, but he pulled me into a hug.

"Oh! OK!" I said, returning the hug.

Thomas was about Ed's height, also slim, but with more feminine features than Ed's surfer body.

"Ed told me so much about you, I'm glad that you decided to join us!" he was saying.

We poured about two-fingers of scotch into glasses and enjoyed some conversation in the living room. Ed was mostly in the kitchen though, and soon called us to the dining room for supper. We had a great meal and good conversation. I learned how they'd met and a bit more about their relationship. They clearly enjoyed one another, but also liked to open things up a bit. Ed, as he noted before, was a bit bisexual, whereas Thomas was strictly gay.

"I guess you're more like Ed, then?" Thomas asked me.

"I would say so - in fact, I am only recently finding and exploring the side of me that is interested in men."

"Well, then, I'm happy you're here - I'm know that we will be glad to help you explore that! You're a very handsome guy!"

"As are the both of you!" I replied. Even though I'd proven that I can enjoy a guy sexually, I'd not really thought too much about the real attraction side of things. Ed's face was certainly more masculine than Thomas's, and looking at the two of them, I did find myself attracted by the more feminine look of Thomas.