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GAY SEX STORIES

The Crossroads

The Crossroads

by Willwor4wine
19 min read
4.71 (2600 views)
gaybisexualthreesomemmfgroup
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Tyler and I had been living together for three months and were both experiencing an evolution of sorts. Prior to meeting, the only gay sex I had experienced was with some casual experimentation in college and with Bob, an older guy I had casually met and at the club where Tyler and I met. While Tyler had been far more active, he had not been involved in an actual relationship, focusing purely on sexual engagements. While both of us continued to enjoy an open relationship and routinely spent time at the club letting our inner sluts out, our shared connection was leading to both emotional and behavioral changes.

Until we had met, both of us had been exclusively bottoms, but together, we discovered the pleasure of being fully versatile and fucked each other every day. That said, we were also becoming more feminine in our mannerisms and preferences. We slept together every night and kissing and cuddling were now routine and enhanced by a growing emotional bond. Tyler had also discovered the joy of being smooth all over and we now kept our bodies total bare, including legs and underarms.

While we still maintained a very reserved public persona, in private, our mannerisms and physical movements had become distinctly more feminine. Added to this, I had developed a strong preference for dressing more feminine, now exclusively wearing women's panties, thongs, and lingerie, and even experimenting in our apartment with makeup and women's clothes, including a growing collection of women's heels.

We had also started discussing a move to somewhere more aligned with our lifestyle and preference. Key West was on our shortlist, but we knew any move would be at least six months away when our current lease expired. That plan though was about to get a major adjustment.

I only worked a half day on Friday's and it was just after 12:30 when I got back to our apartment complex. I always took a shortcut through the central courtyard and pool area to our unit, when I noticed a very attractive girl about my age sunbathing in a very skimpy string bikini. She looked familiar and it suddenly hit me. This girl had been the roommate of the girl I had gone home with that night at the Crazy Eight when I was drunk off my ass.

That night seemed like forever ago, but I still remembered the next morning, when I was still in bed with Rhonda and her roommate came into the room and bounced on the bed, wanting to join us for a threesome, causing Rhonda to yell at her until she left. 'Beer goggles' had been in full effect the night before, so I had zero interest in doing anything else with Rhonda, but her roommate was a different story. I clearly remembered how hot she was...and seeing her sunbathing by the pool confirmed that fact.

She recognized me too and leaned up on her elbow, "Hey, don't we know each other?"

"Ummn...sorta. A little over six months ago, I...ahhh...ended up spending the night at your place with Rhonda."

"That's right! I probably still owe you an apology. I was horny as shit and when I saw that Rhonda actually had a guy in her bed, I decided to see if I could have some fun too. That was probably seriously rude of me. I'm sorry. Rhonda was seriously pissed and is convinced I scared you away."

"Trust me...you definitely didn't scare me away. You actually made me very tempted to stay, but...I never should have allowed myself to be there in the first place. I had...well...I had had way too much to drink that night and wasn't thinking straight."

"Maybe...but at least you were thinking straight enough not to fuck her. She had been trying to get a guy to knock her up for over a year...wanted to get married and figured that was the best way. You were smart to steer clear of all that...a lot smarter than the local hick a few months later who did knock her up."

"Seriously?"

"Yah. And then he felt like he needed to do his "manly" duty and proposed to her. It was all seriously fucked up and I couldn't wait to get out of there. I only knew her from work and initially thought that she'd be a good roommate...she seemed like she wouldn't have any issue with me bringing guys home whenever, or girls for that matter. But she would get super jealous. It just became totally fucking stupid."

"So you moved out and into this place?"

"Yah. Just finished moving in a few days ago. The first day I had free to enjoy the pool. I'm Teri by the way. So...you live here too?"

"Hi Teri, I'm Brandon. Yah, I have a place on the second floor with a roommate."

"Ohhh. Girlfriend?"

"No...just another guy," I tried to say as casually as I could.

"That's cool...wish I had a roommate. Would definitely save on the rent, but it's worth it having my own space and being able to do what I want. Hey, it would be really cool to begin meeting some people here. If you all don't have any plans tonight, wanna come over? I got a new grill and we could break it in with some burgers."

It was so odd...I hadn't looked twice at a girl in three months, but for whatever reason, there was something about Teri that had caught my interest. There was like some kind of draw I felt, almost like we were magnets attracting each other. "We don't have any plans, so yes. What time and what can we bring?"

"How about 6?"

"Perfect."

"And you all wanna bring some beer over? I'll take care of the food."

"Sounds good. Any preference?"

"I'm pretty easy going...as long as it has alcohol in it, but Corona with some limes to add is my fav."

"Mine too. What apartment number?"

"112."

"Ok then. We'll see you at 6 pm, apartment 112...and we'll bring the beer."

As I walked to my apartment, I couldn't understand why I was excited, and why I thought Tyler would be too. She was a girl, but for some weird reason, she felt like a kindred spirit. Maybe I was just making it all up.

Tyler could tell I was excited about meeting Teri and actually seemed excited to meet her too. He could tell I was a little nervous about telling him and reminded me that jealousy had zero to do with our relationship. He also reminded me that girls always have girlfriends and I seemed to be leaning that direction these days so it made sense. He added he still got turned on watching all girl porn too, and there was absolutely nothing wrong with fucking around with girls. Damn he was cool.

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I ran out to the store and grabbed a couple of 12-packs of Corona and three limes, and we headed over right at six. Both Tyler and I dressed casually in cutoffs, t-shirts, and sandals. These cutoffs weren't nearly as short as the ones I would wear to the club, but still very short by today's standards, exposing just the bottom end of the inner front pockets.

We knocked and a few seconds later, Teri answered the door. She had clearly gotten the message and dressed nearly identical to Tyler and me, except her shorts were far shorter, barely covering her ass and instead of a t-shirt, she wore a white cotton, sleeveless button-down that was tied at the bottom, exposing her lower belly. She had also left four buttons at the top undone and clearly wasn't wearing a bra, exposing a fair amount of cleavage. As we walked in, Tyler turned to me and mouthed, "wow."

We did introductions and I opened a beer for everyone while Tyler helped Teri get the charcoal lit. Her apartment was very similar to the one I had initially lived in, with one bedroom, a living room with attached dining area, kitchen and a single, full bath. The furniture wasn't new, but was in good shape and everything was neat and tidy.

By the time we had the burgers ready, we were all on our third beer and laughing and exchanging stories like old friends. Teri had to give Tyler her impression of the morning with Rhonda while I listened in mock horror. It was clear she was very comfortable with herself and her body since she left nothing out, including how she had pulled off her sleep shirt in hopes of enticing me for a threesome.

Tyler played the innocent, "So...if there had been a threesome, would it have just been you two on Brandon, or a full threesome?"

"So, the short answer is that there was zero chance of having a threesome. Rhonda was way too insecure to have ever let me play with one of her dates. But to answer the question you were really asking, neither of us had any issue with girl-on-girl play. She and I played around sometimes and while she considered it experimenting, I have no issue openly admitting to being bi.

Just like there are guys I'm turned on by and ones I wouldn't fuck in a million years, the same goes for girls. Rhonda wasn't attractive at all, but she did have a nice body, which got me most of the way there, so to speak. The thing is, I'm in it for the pleasure, so girls can be just as fun as guys, but Rhonda was in it to find a husband, so unless she was really horny, girls didn't do anything for her."

"That makes sense. Thanks for being so open," Tyler said.

"It's a lot easier to be open and honest, and you both seem pretty open minded, unlike most of the people in this hick town."

"We'll take that as a compliment," I said.

"Besides, unless I'm totally wrong, you two are actually more than simple roommates," Teri said in a very matter of fact way.

"Excuse me," I said.

"Come on...I spent two years in college thinking I might be lesbian and had several close guy friends who were closeted. They did a good job of being discrete for the most part, but you could tell if you knew what to look for, especially guys that were dating each other and it's pretty obvious with you both."

"Like what," I asked?

"Just occasional mannerisms you both let happen now and then and the way you look at each other. And you both shave your legs. If I had to guess, I'd say you're both bi, even if you think you're gay. And you've been undressing me with your eyes all evening," she said looking at me.

I looked over at Tyler and he looked at me, a little surprised by her comment, knowing I had been doing just that. I could tell we were both unsure where to take this conversation and what to admit, but Teri threw us a lifeline.

"Look, I'm totally cool with it and am actually glad to have met two people who aren't total rednecks and have a more liberal view of how to live. I've been open about being bi and while guys think that's hot, it wouldn't be a good thing for me either if people knew. This town is way too close minded...just like most everyone in this state, except for a few people at the universities."

I looked at Tyler and he nodded just a little. "Ok...busted," I said. "I had no idea it was that obvious."

"Trust me, 99% of the people here wouldn't ever have a clue. Like I said, I've just been around enough gay guys to see the tells."

"But you said we're both bi? I mean...yah, I'll admit to having imagined you naked, especially since I've seen you naked before, but I guess I hadn't really been thinking about myself that way."

"Me either," Tyler said. "I've only ever been with guys, although I'll definitely admit to finding you attractive."

"I mean, I guess you could both be truly gay...and yah, gay guys still know when a girl is attractive, but real gay guys I've known don't have that certain look in their yes," again she said looking directly at me. Maybe I'm imagining it...or just wanting it, but it's definitely there."

"Maybe we should do a little experiment," I said with a more than obvious grin.

"You mean, like me getting naked and seeing if you both get hard?"

"Hmmm...tell you what...why don't we all get naked and see what happens? If you both get turned on by what you see, then we can just take it from there and enjoy ourselves."

I looked over at Tyler. "Why not...sounds fun," he said.

"Oh...just one more thing," Teri said. "If we do decide to have fun, you have to promise it will be a real threesome. I'd love to see you two get it on too...watching guys together is seriously hot."

"Sure...works for me," I said.

"Me too," Tyler added.

With that, we all got up and began undressing, which took surprisingly little time as none of us was wearing any underwear. Teri's body was just as lovely as I remembered it, full, firm breasts with brownish aureoles and long, thick nipples. The first time, I hadn't gotten much of a look at her pussy, but is was shaved except for a thin landing strip. Her lips were full and pouty, with visible labia poking out. Fuck, it's like her body was built for sex.

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Tyler and I both were semi aroused, our cocks curving out in front of our balls. Teri just stared at our bodies. "Damn...I've never seen a guy shaved bare before, much less two. That's hot as fuck."

"I actually got Tyler into it. You didn't see, but I was shaved bare when we first me. A former girlfriend of mine got me into it. Hated hair for oral sex and I decided I like it so I kept it that way."

"It looks amazing on you both," she said, licking her lips. "Why don't you both sit down side by side on the sofa," she said with a naughty smile. We both sat down on the sofa, our cocks now standing out in front of us, nearly hard.

Teri got on her knees in front of me and smiled. "Rhonda actually told me later that you were shaved bare and having a smooth, hairless cock in my mouth has been a regular masturbation fantasy of mine," she said as she took hold of it then proceeded to run her tongue around the head. She used her thumb and index finger to open my peehole and licked it several times with the tip of her tongue.

"Fuck dude, she does that just like you do," Tyler said.

Teri looked over at Tyler. "Does he like swallowing what comes out of it too?"

"Oh yah...he definitely does...every drop."

Teri returned to my cock, licking from the base to the tip, then opened her mouth and slid it in, taking more than half of me as her tongue swirled around the shaft as she inched lower until the head was at the back of her throat. She pushed just a little more and the head slid in, her lips hitting the base of my cock and eliciting a low moan from me.

"Feel good," Tyler asked?

"Don't get jealous, but her mouth feels as good as yours. It's like velvet."

"He doesn't need to be jealous...he can feel it too," Teri said as she pulled off my cock and moved between Tyler's legs and repeated the same, taking him to the base, then sucking him in long, steady strokes. As she did, she took hold of my rock-hard cock and slowly stroked me in tempo with her sucking. A minute later, she sat back.

"I assume you both know you have almost identical cocks...and they're both perfect I might add. Oh...and your precum tastes the same too...And I think smooth cocks have just become my new favorite."

Teri spent the next ten minutes switching back and forth between us, never sucking long enough to get us close, but keeping us nice and hard. Her mouth really was incredible. Finally, she sat back. "Ok, time to switch things around."

Teri stood up and we both did too. Teri then sat down in the middle of the sofa with her legs spread wide. "Tyler, stand on the sofa in front of me so I can continue enjoying your cock. Tyler, let's see if you're any good at licking pussy."

As we switched around, I noticed that while my own cock was still rock hard, Tyler's was only semi-hard, even though Teri had just been sucking him. Tyler climbed onto the sofa and stood in front of Teri, who once again took his cock in her expert mouth. I kneeled down between Teri's open legs and took a closer look at her bare pussy.

She looked totally smooth and I ran my fingers over her pubic area, confirming the fact. This was more than shaving. She either waxed, or had done something permanent, like laser or electrolysis. I'd have to ask her later.

She was definitely very aroused. Her outer lips were swollen and with her legs spread, the wings of her labia were open, revealing that she was soaking wet, literally almost dripping. I leaned forward and kissed in the middle of the opening, my touch eliciting a moan from her. I ran my tongue between her labia, tasting her flowing juices.

I had become very accustomed to the taste of male cum over the past few months and Teri was definitely sweeter and more mild tasting, but equally pleasant to me. Given how wet she was, I had to assume she was probably a squirter, which might be fun to experience.

I kissed my way around her sex, avoiding her clit, then concentrated on her labia, licking deep between them, Teri's hips pushing up into my mouth as I did. I had always enjoyed doing this to Samantha, especially given how smooth she was and Teri's pussy was equally enjoyable. I had to admit to myself that I missed it.

I went slowly and made sure to avoid her clit, purposely working to bring Teri close to an orgasm, but not taking her over the edge. As I licked her, I slid my right hand under her ass and began teasing her tight little asshole with a finger, causing another series of moans and a noticeable increase in her wetness level.

Teri finally pulled back from Tyler's cock. "This is pretty fuckin' hot and you definitely have a talented tongue Brandon, but I want to see the two of you play together."

Brandon stepped off the sofa and Teri moved over to the chair a few feet away as Tyler and I positioned ourselves into a 69 on the sofa. Neither of us wasted any time in taking the other's cock as Teri began masturbating as she watched.

I had been incredibly aroused this entire time and my cock was rock hard as Tyler took it in his mouth. Tyler's cock on the other hand was only semi-aroused which was odd given that Teri had just been sucking him. I knew from personal experience just how talented Teri's mouth was so had to assume that Tyler just wasn't all that into it. It took less than a minute though before his cock was full and hard again as I sucked him and took him down my throat.

This entire scene was pushing me towards the edge and I finally pulled back from Tyler's cock and looked over at Teri. "So...who do you want to see fuck who?"

"Oh fuck," Teri said breathlessly. "I want to see you fuck Tyler."

Tyler got off the sofa and got on all fours in front of Teri, giving her a great view of the action. I kneeled behind him and began running my wet cock up and down his ass. "You wanna help guide me in," I asked Teri?

She just bit her lower lip and nodded. Tyler held his cheeks open, fully exposing his asshole as Teri rubbed the head of my cock over it. Teri leaned over and licked up the length of my shaft then over Tyler's horny hole before depositing a glob of saliva on my head as I began to push forward, my head spreading Tyler's asshole as it accepted me.

Teri was mesmerized as my cock began sliding into Tyler's ass, his hole opening to accept my girth as my shaft disappeared inch by inch into him. I began to fuck him in a slow, steady rhythm going deeper each thrust until I was fully buried inside him. "Fuck...that's sooo fuckin' hot," Teri said in almost a guttural moan. I held his cheeks open with my hands, giving her a perfect view of the action.

As usual, Tyler's ass felt like silk. He knew how I liked it and relaxed his ass, letting it gently caress my cock. He was warm and increasingly wet, his own juices mixing with a generous amount of precum I knew was dripping from my cock.

Our bodies got into a steady rhythm as his hips pushed back against my cock as we fucked. Being watched by Teri had me incredibly hard, the veins of my shaft hard and very visible. With her free hand, she reached over and caressed my bare public area, clearly enjoying the look and feel.

I reached over between her legs and slid my middle finger into her soaked pussy, then a second, which went in as easily as the first. I finger fucked her at the same pace as I fucked Tyler's ass, her body responding with small jerks. Suddenly, I felt a wave of heat spread over my hand as Teri came, a stream of hot cum pouring out of her orgasming pussy, her hips bucking down onto my hand.

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