Double Headed Dildo Drama (Follow-up to the Alyssa story) [m/f]

So after that one night with Alyssa things pretty much went back to normal. Neither of us mentioned what happened, and if she seemed to ignore me a little more than before in social settings no one really noticed. I just figured that in the clear, sober light of day she realized what happened and thought it was a mistake. And while I felt a bit dejected, I couldn't really blame her. I guess when you've been facialized by a friend you've never really had feelings for, you can feel a bit awkward about social interactions with them.

But did she have feelings for me? Besides drunk and horny? Was there a reason she called me, or was I just available? Was it interest or luck?

I spent about a week with these thought churning through my head. It felt like high school awkwardness all over again. But after a little while, and no signs from Alyssa whatsoever, I was able to just chalk it up as a fun experience and a small boost to my ridiculously small self confidence.

Then a few months later, she called me again.

Her boyfriend Chad was "out of town" again (i.e. cheating on her), but he'd been doing that fairly regularly since our last encounter. I'll admit the first time he was out I got my hopes up, and then dashed as no call came. So this one struck me out of the blue. Not only had she called me, she was sober.

"Hey, DJ," she said, sounding almost nervous, "can you drop by real quick?"

It was another Friday night, the dorm was empty, and I was sitting on my ass playing Star Craft or something. "Um, sure." I said, not quite sure where this was headed, but trying not to get my hopes up.

I tried not to run up the stairs three at a time to get to her room. My heart was pounding enough as it is. I paused in front of her door in a futile attempt to calm myself, took a deep breath, and walked in.

No candles this time, no corset, no drunken giggling. Just Alyssa, looking plain yet beautiful, sitting on her bed, nervously chewing on a nail.

The good-guy side of me took over, clearly seeing a damsel in distress, and washed away all my awkward horniness. I sat down beside her, took her hand in mine and asked what was wrong.

"It's just…" she started, then sighed heavily, and then unleashed.

"Chad's cheating on me again. And you know it, and I know it and everybody knows it and it's okay, I mean I don't like it, but it's who we are. As a couple. It's what he does. But I'm tired of it. But I love him. And I don't want to break up. But we never have sex anymore. And I'm horny. And I love him and I don't want to cheat but I need something and I need someone and I need…"

"I need someone safe. I need someone who isn't going to try and break us up. Or brag to everyone about what we did. And I know we did that one thing once and maybe it didn't count and he's your friend and you're nice and I really, really enjoyed what we did last time, and…"

She finally looked up at me, her eyes sad but passionate. "Can we… can we do something like that again?"

I try not to brag, but I have to say, I was cooler than motherfucking Fonzie at that point. Everything inside me went to all hands battle-stations, full alert! But all I said was, "If you really want to, Alyssa, sure. I think I'd like that too." with a kind smile.

Cooler. Than. Fonzie.

"You still seem upset though. Do you want to wait a little while?" I asked, being gentlemanly as fuck. (Luckily she was nowhere near my pants so she couldn't feel the nuclear meltdown that was happening in my boxers.)

"Um. No. But, um… would you be okay if we kissed a little? That's not really cheating, right?"

By response I simply leaned in to meet her lips. They were soft and slightly pouty. We kissed simply and with no tongue. Our bodies leaned in together. She wrapped her arms around my neck as I ran one of mine around her back, the other caressing her knee.

A few more soft pecks and her tongue slid out to explore. Just the tip, gently working around my lips before tentatively sliding in. When our tongues touched in my mouth, it was like a bolt of electricity that sent everything into overdrive. Her fingers dug into my back, pulling me closer. I grabbed on with everything I could, my free hand sliding up to her chest.

Over the shirt, over the bra, I didn't care, just feeling one of those big, beautiful tits in my hand made the world disappear. I was the one that felt drunk now. The world spun around me and was reduced to me and her, touching and kissing and groping. I wanted nothing more that to rip her clothes off and have my way with her. Throw her back and pound the shit out of her pretty pink pussy. Fill her with my cum until it spilled out onto the sheets. And I knew if I tried she would let me.

But a tiny voice in the back of my head said no. Stupid voice. Here we were, practically cheating on her boyfriend, one of my good friends, already. Why not go the extra step? It would serve him right! But I knew she didn't want that. And if she didn't, I didn't.

Gasping for air, I pulled back. A quick look at Alyssa confirmed that she must have been having the same thoughts. And although her cheeks were flushed and her eyes were on fire, she took a second to look away from me and gather her thoughts. When she came back to me, she had that same devilish look I've come to love.

"So, I believe I promised you a show last time…"

"What? Oh! Wow. Um. Are you sure that's clean?"

Alyssa crossed the room to pull out the double headed dildo her roommate kept hidden in her dresser. "Yeah, she doesn't really use it. Turns out it was a gag gift," she mimed deep throating the thing, "no pun intended."

"Oh." I said, laughing. "And the strap on?"

"No, that's from one of her old boyfriends. He liked getting drilled in the ass apparently. Though I'm still not sure she's not bi."

"Now. Get your ass over here." she said, patting the chair opposite her bed.

Alyssa turned on some music and started doing a strip tease / lap dance. Slowly removing her clothes, grinding against my crotch. Softly running her tits across my face, tantalizing me with her nipples, knowing I wouldn't try anything. It was a dizzying combination of freedom and safety and sexiness and, really, just pure evil. (Something like this actually) It's a good thing we agreed no touching, because I think I'd come instantly with the slightest contact with my dick at this point. Hell, just remembering this kinda has me on the brink.

After what seemed like a hellish eternity, Alyssa finally strutted over to the bed, those beautiful healthy cheeks bouncing with each step, and laid down on the bed. With grand theatricality she spread her legs, touching her wetness with an exaggerated porn style moan.

"Now remember," she said, clearly back in control of her senses "you stay over there." She smiled and began to run her hands all over her body. Groping and squeezing and playing. "But feel free to get comfortable as you watch."

I remembered she seemed to get off on watching me play with myself as much as I did her, so I took what little self control I could muster, leaned forward, and said. "I'm perfectly comfortable right now."

She pouted and made a cute little mou, but quickly recovered and said, "Let's see how long you can stay that way."

She placed the double headed dildo between her copious breasts and began to stroke it. More porn moans and toothy snarls, with lots of eye contact, only to be broken when she went down on it, still jerking it off with her tits. It was a sloppy, noisy blowjob, with lots of drool dripping down the shaft of the toy. Once it was good and wet she laid back again, lifting her legs in the air.

"This is what you were waiting for, wasn't it?" and she spread her ass cheeks, revealing a pert little asshole, twitching in anticipation. Anal was clearly not new to her, as it took little time for her to slide one end of the purple monstrosity into her opening. I may have scooted the chair closer at this point for a better view.

Closer than I thought, apparently, because Alyssa rested her ankles on my shoulders and pulled in closer. She had about 3-4 inches of the dildo inside her already, and was slowly pumping back and forth, trying to get another inch inside. I had abandoned all pretense at this point and gotten my cock out. Slowly stroking and trying to keep control. My other hand caressing her silky leg next to my head.

Seeing my cock flipped a switch in her, because she quickly bent the dildo in half and effortlessly slipped the other end inside of her with a loud gasp that settled into a growling moan. We instantly matched up our rhythms, my stroking and her pumping slowly building in speed and intensity. Just as I was getting close again, she stopped.

"Here," she said, letting go and freeing her hands to play with her tits. "you do it."

Again, I could have exploded at those words.

Tentatively I reached out, one hand on each end of the toy. I started by doing what she did, pumping each end at the same time. Slower, though, as I wanted to watch it slide in and out of each hole. It wasn't long, however, before I started to switch it up a bit. Alternating fast pumps, pussy, ass, pussy, ass. Alyssa seemed to like this as she began to squirm on the bed and pull at her nipples. I could tell she was going to come soon, so I kept going with the same thing, not wanting to ruin her momentum. It was a quiet, breathy orgasm, and I knew she had more.

I took that opportunity to ramp things up. For the top half, I started doing long pounding strokes in and out of her pussy. Really hammering away and making sure that my knuckle hit her clit with each stroke. At the same time, I started doing short fast strokes in her asshole. Barely even pulling it out, almost vibrating it in place. My idea had the intended effect.

Alyssa started screaming almost immediately. She grabbed a pillow to cover her mouth as her other hand clawed at the bedsheets. I knew she was going to come soon, so I upped the speed and really leaned into it. Just like last time, she exploded into a body shaking orgasm. She tried to push my hands away, but I wasn't having any of it. I kept going and I could see one orgasm rolling into the next. Her body spasming, stomach tightening, legs grasping the back of my head. Those perfect tits jumping every which way. After at least four orgasms I finally slowed my pace and stopped.

I let go of the toy and leaned back to inspect my handiwork. Alyssa lay across the bed, spread eagled and limp. The pillow was still across her face, unattended. The dildo slid out with a wet pop, breaking the silence. Any other time I would have laughed, but I was too hard, too horny, to ready to unleash on that beautiful body.

Alyssa wasn't so glib this time. She barely had the strength to pull the pillow from her face and say, "Cum. Now."

I started to stand up to get closer to her chest, but she pushed me back down with one foot. "No. Pussy." She had regained enough coherence to be cutely pouty about it.

"I want to feel that warm cum of yours all over my pussy. If I can't feel you inside me, I want to at least feel part of you inside me."

I briefly hesitated before I remembered she was on the pill, and that was all the encouragement I needed. I leaned forward, beating furiously at my engorged cock, as Alyssa played with her slippery lips, spreading them, then fingering herself, then playing with her clit, then back to spreading them again. I could feel the heat coming off of her, smell the warm musky scent of her pussy. Watching her play with herself, knowing she wanted me, it was almost too much.

I tried my best to aim, and most of it hit the target. Thick, ropy strands of cum shot out drenching her hot pussy. She started to pull her hand back to allow for better coverage only to slide back in. Rubbing my cum all over her pussy, matting her pubic hair, and fingering herself. Seeing her fingers covered in my cum, sliding in and out of that wet little hole, it was like a reverse cream pie. She was stuffing my cum up inside her. I'd never seen anything like it.

I finished off with my last few spurts and then collapsed on the bed next to her. I figured we knew each other well enough at this point to lie naked beside one another.

We took a few minutes to catch our breath before she said she needed a shower. I threw on my clothes, gave her one last peck on the cheek, and left.

That was my last experience with Alyssa. Somehow, though, the awkwardness from after the first time was gone, and we were right back to being the playful friends we were when we started.

Alyssa did finally break up with Chad about a year later. We don't really keep in touch, but I know she's married now with a few kids and quite happy. I'm certain her husband is quite happy, too.

Source: reddit.com/r/gonewildstories/comments/395u7z/double_headed_dildo_drama_followup_to_the_alyssa