Shortly after graduating college, I moved to a new town where I didn’t have many friends close by. This led to me cruising facebook a lot to find old acquaintances that lived in or near my town. During this time I reconnected with an old high school friend named Amanda. She had always had a crush on me, and I always thought she was cute, but we never dated. She was still adorable. She was 5’6” 140 lbs with curly brown hair and lots of freckles (which I love). She was not well-endowed up top with just A cup tits, but her booty was wide and plump… just the way I like them.
Now for the bad news… she lived 4 hours from where I was currently living. Bummer. But that didn’t stop us from messaging constantly on facebook. At first our messages were innocent and rehashing old memories. Then I got flirtatious by teasing her about her crush on me and saying how it was too bad we didn’t live closer. She shot back that I wouldn’t be able to handle her as she had gotten a bit more wild since high school. This piqued my interest. Just how wild?
Our messages got VERY naughty after that. We talked about past partners and sexual experiences. Amanda thought it was so hot that I was bisexual. We shared our deepest kinks that we hadn’t yet got to act on, and we happened to share one in common: anal play. Sure, we had both done anal and enjoyed anal play while we masturbated, but neither of us had done true ass worshipping with another person. But we both wanted to just dive in and make out with another person’s ass, slide in a finger or two, use some toys, and just have another person sit on our face and smother us with their asshole.
Then began the dirty emails to each other. Nearly every day I was greeted with a new picture of her ass. Amanda sent pics of her ass in tight jeans, in a thong, spread open, with a finger in it. Nearly every imaginable scenario. I reciprocated by doing the same. I don’t have a ba-donk-a-donk like her, but she seemed to love the pictures of my skinny little ass. I had plugs and vibrators that I would shove in me and snap a picture. She said she wished she had a strap-on to fuck my tight little hole. We also sent more traditional sexy pics of tits, pussy, dick, etc, but we heavily skewed towards ass pictures.
After weeks of trying to match our schedules and meet up at a hotel halfway between us, the stars aligned. We booked a semi-nice hotel in a city halfway between our respective cities. The plan was simple: have a light dinner and drinks, take a shower, and worship some ass.
I got to the hotel first and checked-in. I got up to the room and unpacked. On the bedside table, I staged my “sex enhancers”: a bottle of lube, a blue vibrating dildo, a black butt plug, and cock rings. I pulled out the bottle of wine I brought too and opened it to calm my nerves. Amanda texted me she was in the lobby. Butterflies were flying around in my stomach. She knocked on the door and when I opened it, she was even cuter in person than I had remembered.
She wheeled her suitcase in and set it down next to the door, and immediately dove into my face for a really hot and long kiss. My cock stiffened immediately, and I thought of abandoning the plan and just stripping her naked right then in there. But senses got the better of me. “Hey now,” I said pulling away. “We need to get some dinner first.”
The whole dinner consisted of footsie under the table and knowing glances at each other. I don’t even remember what we had, but I was feeling tipsy from the wine. We paid and walked back the hotel. The moment the door closed we resumed our passionate kissing from earlier, this time with the clothes coming off. Once naked, Amanda excused herself to the bathroom to perform an enema. Like I said, we wanted to do this right. After she finished, I did the same.
Once she heard I was done, she came back in and started the shower. We took our time in the shower rubbing each other’s bodies all over. I soaped up my hands and moved them to Amanda’s ass crack. I rubbed the edge of my hand between her cheeks and paused to rub a finger against her asshole. I didn’t want to push too hard because I knew soap is not a great lube, but she seemed to want more.
We exited the shower, dried off, and ran to the bed. The making out ensued, but I made the first move. I started kissing down her neck, chest, stomach, and hips. I gave her a devilish look and pushed her over onto her stomach. Her ass was mine for the taking. I grabbed the cheeks and gave them a jiggle. I kissed, licked, and nibbled them a bit. Then the moment of truth. I spread her ass wide open exposing her smooth, pink hole. I dove in, kissing and tonguing just as I was doing to her mouth moments earlier. At first she giggled, but that soon turned into moans.
As I frenched her asshole, I pushed my thumb against her pussy. She was dripping with her juices (and probably my spit too). I slid my thumb into her and used it to gently rub her g-spot while my mouth stayed locked to her ass. She was now pushing back on my face and thumb, and moaning things like “Oh my god” and “That feels incredible”. It only took a couple of minutes until she came for the first time.
After she came down from her orgasm, I told her to stay put. I grabbed a butt plug and lube from the bedside table. After a generous dose of lube, I pushed the plug against her inviting hole. It only took a light push for her whole ass to envelope the plug entirely. She gave a huge moan.
Amanda rolled over with a huge smile and said “My turn!” She grabbed my arms and yanked me down on my back. Her hands gripped just behind my knees and pushed my legs high in the air, exposing my ass to the air. She did not tease at all and simply drove her tongue deep in my ass. Like her, I giggled at first, but soon became overwhelmed with pleasure. She licked and darted her tongue in and out of my asshole meanwhile her hand moved up to firmly grip by cock, which at this point was oozing with precum. Amanda’s mouth would detour to my balls every now again while she stroked me, but would resume making out with my hole every time.
After what felt like 15 minutes, she moved up to my face and kissed me hard, mixing together our spit and ass juices. It was so incredible hot. She broke our kiss and said “I want to fuck you in the ass.”
While we talked about splitting the cost of a strap-on, we never actually did. Those things are expensive! At least the good ones are. So instead, she grabbed the lube and dildo from the table. She lubed her fingers and rubbed against my ass, inserting a finger or two every now and again. After she felt I was warmed up enough, she guided two fingers into my ass and shoved them deep. She started curling her fingers back and forth against my prostate, which make my cock twitch and run with a steady stream of precum. She worked in a third finger and I could feel my asshole stretching, which probably should have hurt, but since I was so horny it actually felt really fucking good.
She removed her fingers and slid in the dildo. Amanda positioned her body so that it seemed as though the dildo was her dick. She started to thrust and with it moved the dildo in and out of my ass. “You love it when I fuck you, don’t you?” she asked seductively. I could only nod as I was so focused on how insane it felt to have my prostate massaged by this dildo.
Amanda reached down and turned on the vibrating function. With new batteries just installed that day, the vibration was stronger than I had gotten used to. I just closed my eyes and let the euphoria overtake me. Amanda noticed this and started fucking me harder and harder. I could feel the wave of an orgasm coming on. I was so tempted to grab and stroke my cock, but I also knew that if I could cum hands-free that it was feel 1000 times more amazing. I just focused on the feeling and clenched my kegels over and over. Within just a few seconds, I climaxed and opened my eyes to see rope after rope of hot cum firing all over my chest and stomach. Looking up at an out-of-breath Amanda, she just smiled and said “Whole fuck! I made you cum!”
After some clean up and cooling down, I returned the favor. She laid down on her back with her legs pinned to her chest. I relubed all of us for good measure and slid my dick into her ass for the first time. Her eyes rolled back in her head, and I knew that she wouldn’t last long. I began fucking her ass as hard and as fast as I could muster. Thrust after thrust, she just kept grunting and squealing. She couldn’t take much more when she finally lowered her legs as her body convulsed into a huge orgasm. She was speechless. I was tired. After a couple of minutes of aftershocks and big breaths, she winked at me.
We called it a night there, but spent the next morning until check-out laying around completely naked and doing some traditional stuff like typical oral, PIV, etc. We still played with each other’s asses, but it wasn’t the main focus.
After parting ways, we made plans to meet up again soon. Which we did. And it was fun. There were moments that I wished we lived a bit closer to each other because it might have turned into something more. After about a year and about a half dozen meet ups, she got a job on the other side of the country. And that was that. But I still play with my ass and cum to the memory of this first time together.
Source: reddit.com/r/gonewildstories/comments/bpl0y7/massive_ass_play_with_a_friend_mf
One lucky guy that’s for sure.