Near miss(ish) with my friend’s gf

I had a small, but tight, group of friends back in college. As you probably know, in situations like this, couples tend to get "recycled", and you can't really hold it against a buddy for getting together with your ex. That said, if a couple was still dating, no matter how rocky, you were expected to back off.

Alyssa pushed that one to the brink for me.

She was dating a good friend of mine, Chad. Alyssa and Chad (obviously not their real names) had been together for as long as I'd known them. Sure, they'd break up from time to time, or cheat on one another (usually instigated by Chad and then Alyssa for balance), but they'd been together almost three years.

On the night of this story, Chad was out of town to visit "friends", which inevitably meant he was getting drunk and picking up some floozie in a bar a few towns over. Alyssa knew this and was having her own private party in her dorm room with a cheap bottle of vodka. That's when I got her drunken call.

"DJ, you've got to come over! Right now!" she slurred into the phone.

I sighed, preparing for another long night dealing with a drunk Alyssa. "What is it?"

"My roommate is a total lesbo!"

"And she's hitting on you?"

"No! She was out! And I was going through her drawers! And I found a strap on! It's huge, DJ! A huge strap on! You have to come see this! It's hilarious! She totally wants to fuck me with a huge red strap on!"

I knew from prior experience that if I didn't stop by to entertain her antics I'd end up with my phone ringing off the hook all night by a bored, drunk girl pouting that she didn't get her way. It was easier just to stop by and humor her.

Alyssa and I lived in the same dorm. It wasn't quite co-ed, but guys were on the ground floor and girls were on the top, with nothing barring the way between the two. It was late, so I really shouldn't have been up there, but it was also Friday night, so it's not like there was anyone left in the dorms except shy lonely dudes and drunken chicks.

I knocked on her door and was greeted with a drunkenly sexy "Come in…" followed by some giggles. The room was lit but a dozen candles and Alyssa was draped across her bed, trying to look sultry (and only missing the mark slightly), wearing a black lace corset, garter belt, stockings, the works. She was a short, thick girl. Not chubby, but not slim either. The outfit clung to her, and the corset was doing its best to hold back her massive breasts. I'd never really been interested in her before, but I won't lie, my dick did start to wake up a bit.

I sighed and closed the door. "Alyssa, what are you doing?"

"I'm going to fuck you in the ass!" She shouted, and pulled the strap on out from under the bed, waving it around maniacally while collapsing in a fit of laughter.

"Holy shit, you weren't kidding." I said. "Though to be fair, Tina may use that on guys instead of girls. So she may be straight." I pulled up a chair and sat down, ready for a long night.

"Oh no, that's not all I found! Here, it's right behind you."

I started to turn, but Alyssa had already bounded across the room in a surprising display of dexterity. She straddled me and reached behind me for something with both hands. This, of course, had the result of my face being pressed between her tits.

For a moment, all rational thought went out of my head. My face was completely enveloped by her massive cleavage. Her big, soft tits rising up on either side of my head, cool against my warm skin. It was an odd, blissful moment. I could have stayed there forever. But as soon as it happened, it was over, with Alyssa sitting back on my lap and her arms on either side of my shoulder. If she'd done it intentionally, she was showing no signs. She was, however, grinning wickedly.

"Guess what else I found…" she whispered, as I felt something cool wrap around the back of my neck.

"A double. Headed. Dildo." And sure enough, as she slid it across my neck and nestled it into her cleavage, there it was. About two and a half feet long and purple. Alyssa started pumping it up and down between the flesh spilling out of her top. I was shocked, horrified, and then mesmerized. Also, was that a nipple trying to poke out?

"See? Total lesbo." she smiled triumphantly.

"Um," I said, trying to form a cohesive though, "possibly. Although there are girls who can use it on themselves. For. Y'know. Double penetration."

"Ugh! You're such a perv!" she said, and slapped me on the forehead with one end of the dong. "But the good news is," she threw the dildo over her shoulder and came in close, "that's exactly what I'm looking for tonight."

Again, I won't lie, I was doing everything I could to keep my dick from raging at this point. Her legs were wrapped around me, squeezing. She was not quite grinding against me, but rocking back and forth softly. Her breasts were pressed against my chest and her lips were centimeters away from mine. "Alyssa…" I protested weekly.

"DJ…" she mocked back. "We both know what's happening. Chad is out fucking some bar slut. I'm drunk. And you're here. And my pussy is aching. I need a good. Deep. Fucking. And right now, you're my best choice for that." she punctuated each word with a hard grind against my cock. At this point there was nothing I could do. I had one of the hardest erections of my life. Even though I was wearing jeans, I knew she could feel it. "And don't tell me you're not interested too." She finished rolling her hips in circles across me to emphasis your point.

To this day, I still can't believe the following words came out of my mouth. "No. I can't." I sighed. "You're still dating Chad, and you're drunk. You're not making good decisions right now."

"Maybe not" she said, "but that doesn't mean I'm making bad ones." She said as she got up and walked back across the room, her ample ass bouncing pleasantly with each step. "Tell you what. I'm just going to fuck myself," she picked up the double headed dildo and waved it at me to underscore her point, "and you're going to watch. And whatever you happen to do while you watch… is up to you. No penis in no vagina, no touching, no cheating right? Just two friends… " she said, sliding the tip of the rubber cock across her lips, "hanging out…" with one fluid motion she had swallowed a good 5 inches and then slipped it back out just as gracefully, "having fun." she finished, smiling deviously.

By this point I couldn't catch my breath. My heart was in my throat. My ears were pounding. And my hand found its way to the front of my pants, rubbing the outline of my erection. My eyes were locked on Alyssa.

Her eyes sparkled as she knew she'd ensnared me. Wasting no time, unsnapped the top of her corset, allowing her massive E tits out. She had large, dark areolas with thick, hard nipples. She lifted one breast up, never losing eye contact with me, as her tongue snaked out to lick her nipple. A couple of soft wet circles, then a flick or two, and then she sucked it hard into her mouth. I swear to god I could've cum right there.

"If only that was you mouth… your hands." she moaned, "Your cock…" as she began to stroke one side of the dildo between her tits, flicking at the tip with her tongue and sucking on the head. My breath came faster as I slouched on the chair, legs spreading, not even trying to hide the fact that I was groping myself thinking about her.

"Oh god, DJ… don't you know how bad I want you? Look at how wet my pussy is…" She teased as she leaned back a bit and spread her legs. She pulled her panties to the side, and even in the dim light of her room I could see the dark wet stain. Her lips were fat and puffy, and when she spread them you could see her pink, wet, hole glistening in the candlelight. Twitching, contracting, "Waiting for your cock."

"But I guess this will have to do." She signed melodramatically as she took the end of the dildo and ran it up and down her pussy lips. "Since I showed you mine, can I at least see yours?" she pouted as she batted her eyes.

Let's be honest, we all knew I couldn't hold out entirely, right? I tried to be as suave as possible, but I know it was more of a flailing rush to undo my belt, my zipper and pull my pants and underwear to the floor. My cock's not long, only slightly above average, but it is thick. About 6.5" circumference (99.97%ile. Thanks howlongismyschlong!) so it usually gets some reaction.

Alyssa was no different. She gasped and slid the toy deep inside herself, almost unconsciously, prompting another louder gasp and moan.

We were both so charged up, the rest of the evening didn't last long. I stared hard at her body, laid out before me, as I began to pump slowly. Showing off for her as much as she did for me. Soon our eyes locked and our paces synched up. She was cramming as much of that dildo as she could up inside that aching pussy. Her other hand roamed from her tits, grasping and groping and pinching and pulling, to her clit, rubbing and flicking and slapping.

I could tell we were both getting close, so I stepped out of my pants to go stand next to her. "Yes," she moaned, eyes half closed, "please… cum on me… I want your cum…"

"Where?" I half moaned, straining to hold on to the huge load that had built up from the night's teasing.

"Anywhere, ungh… everywhere… mmmm… my… my face…. my tits… I want your cum…. please DJ…. plea-" and it was as this point that she orgasmed. A long, body shaking release. Her eyes literally rolled back in her head as her whole body was wracked with spasms. Her tits bouncing everywhere, her thighs quaking, moaning and gasping and grunting.

After what seemed like an eternity she finished and lay there, spent. Her eyes slowly fluttered open and focused on my cock. Head dripping with precum, just waiting for the right moment.

"I meant what I said," she said as she sat up in front of me. "I worked for that load you've built, and I want it all." She smiled and cradled her tits, opening her mouth wide and sticking out her tongue. "Give it to me."

That was all I needed. I let go to everything that had been pent up inside me. The first burst was a thick strong jet that splashed across her cheek, into her mouth, and dripped off her chin. She moaned orgasmically as it hit. The next few rounds found their way to her face as well, and then I aimed lower to glaze her tits and empty my sacks. When I was finished she was covered in thick white cum and she lay back, basking in it.

After a brief moment she began to wipe the cum away with a finger and clean it with her tongue. Her eyes lit up and said "I thought I saw you drinking pineapple juice in the cafeteria!"

I just laughed and dropped back down into my chair, exhausted. I wasn't up for clever conversation.

She cleaned up the rest of my mess quickly and quite appreciatively, then gave me that devilish look and said, "You know. I only ever got to use one end of that thing. Next time I'll have to give you a better show."

Which, if you're interested, is a story I can tell another time.

EDIT Just found this picture today which is a surprisingly close portrayal of Alyssa and her outfit.

Source: reddit.com/r/gonewildstories/comments/390zrc/near_missish_with_my_friends_gf