It started with her new vibrator. The old one had finally died, and so off I went to the adult store to replace it. Just a simple, metallic blue toy, about 6 inches long and about the width of a big permanent marker. Returning home, she took it out of the packaging and looked it over. A little thinner than I expected, she said. Hell, I bet it could go in you pretty easily!
That caught me off guard, I have to say. I had known a few gay guys, and understood that anal play was a thing, but beyond a stray finger brushing against me back there during foreplay, I hadn’t considered it. But… I was intrigued.
I laughed it off that night, but the next day, I was off work, and she worked the morning shift. So I had some free time, and I knew how to spend it. I went up to the bedroom and got out of my clothes. We didn’t have any lube, so I used some hand lotion that was on the nightstand. I spread a bit on the toy, making it slick, and then used a bit more in and around my opening. This was a new sensation, and I was surprised how sensitive it was back there, and how eager I was to continue. I slid the vibe in, slowly and with a little pain, but when I got it a few inches in, it felt amazing! I twisted the control on the vibe, starting a buzzing that pushed everything else out of my mind and began playing with my cock. I came pretty quickly and couldn’t wait to share the news later.
That night, after work and nearing bedtime, I let her know.
Hey, so today I tried something, and you were right.
What?!
So.. I can take your new toy… I said it shyly, kind of embarrassed.
Let me see, she replied.
Back upstairs, did the whole setup again. Lotion on the toy, and started to finger myself, but now with an audience. I could feel her eyes on me, so I closed mine and tried to recreate the moment from earlier. As it slid home again and started pulsing inside me, I began stroking, and felt her hand close over mine, speeding up as I worked the toy in and out. Soon, I felt my balls tightening and the splash of my hot cum onto my chest.
Wow, she said. So, you liked it?
I did, we should think about doing this again, I told her.
As time went on, we did do it more often. It became a regular thing to have her assist my masturbation with the toy, and sometimes she would initiate it, bringing it out during sex or offering it as foreplay. I continued playing with it on my own, and looked for porn similar to what I was doing. I found pegging videos and pictures, and they were a revelation. I felt a little embarrassed at how hard and turned on they got me, so I didn’t mention it. Nor did I mention that while looking for more of them, I stumbled across something I hadn’t even considered: a beautiful redhead woman with a hard cock between her legs. I found trans porn, and I was definitely into it!
Again, this felt a little more taboo than just playing with a vibrator, so I kept it to myself and my private jacking time. But it slowly became my go-to for those times. And then the questions started in my head… was I into this because I was wanting cock? Did I want to be dress up and “be the girl” for someone? I started to experiment a bit more, using a second dildo to suck on while playing, and found that while it was arousing, it wasn’t quite right. I also started trying on some of her clothes while she was out, starting with panties, which were a huge turn-on, and over time, trying on her skirts, bras, and tops, which was also a thrill. But, a thrill I wasn’t going to share just yet.
So it continued, the periodic anal play slaking my growing lust for these taboo turn-ons. Eventually, we hit a lull sexually, and decided to expand our horizons. We signed up for a Netflix-like porn movie service, and ordered a few different things, and then we went to one of those boutique adult stores for couples. We browsed a bit, picked out some lingerie for her, a couple scented candles and massage oils and the like. While we were waiting to check out, she nudged me and pointed to a strapon dildo and harness kit.
What about that, she asked.
I gave a little nod, then we cashed out and went to the car. On the drive home, she asked again, did you want to get a strapon, are you into that?
I said, with a little trepidation, that I wanted one, and yes, I would be into that. We agreed that I would go pick one up, but also maybe a DVD of some strapon play, to give her ideas and insight.
I went out later that night to a different store and picked one up, and the requested movie, along with lube and headed home. We sat down on the couch with some drinks and put in the movie. My chest was pounding, fearing judgment or disappointment. After 2 or three scenes, she turned and said she’d seen enough for tonight. No pegging that night, but not off the table. She needed to process it a bit.
A few days later, I came home from work to find her in a short dress and a devilish grin, and not much else. She stood up and led me upstairs, flashing a naked ass on her way up. In the bedroom, she lifted the front of the dress to show me what else she was wearing: the harness, holding a purple dildo sticking out from her waist.
Are you ready, she asked, pushing me back on the bed and undressing me.
I lay back on the bed and spread my legs as she stroked and rubbed my cock, my thighs, and my ass, grazing a finger across my opening and pushing against it. She dripped some lube onto my hole, working it in gently. Then, joining me on the bed, she knelt with the toy swinging in my face, and stuck it in my mouth. I licked it hungrily, pulling it to the side to lick her pussy as well, and getting both nice and wet. She laid back on the bed, her cock standing up and beckoned to me, saying, Ride me, I want to watch you get fucked.
I straddled her, reaching back to spread my ass open and take it. I slid down it slowly, lowering myself ’til my ass rested on her thighs and my balls were on her belly, and begin rocking forward and back. My ass was filled up, and I was in ecstasy; eyes rolling back in my head. She closed a hand around my dick and began stroking. I wasn’t hard yet, I found it took a little more stimulation up front when attending to ’round back first. Soon, though, I was bouncing up and down and thrusting my hips against her hand, spraying her chest with my cum. I slumped forward, spent, collapsing in a pool of cum and tits and thanked her.
Fast forward a few weeks, with a couple more repeats. It’s time to order new videos from the porn-Netflix thing, and I am browsing. I figured, she hasn’t freaked out over the pegging, let’s see what happens next, and ordered a DVD of MFT threesomes, with some penetration on everyone’s part. A few days later it arrives, along with some other, less deviant fare. Come evening, I hand her the stack of discs and offer her the choice.
Flipping through, she takes in the porn-with-a-plot, something about the hard life of skinny blonde models in LA. No, not interested. The blowjob compilation, maybe, let’s what else we got. Then, as I stand with heart in throat, she reads the label on the final one.
Shemale threesomes?! Really?
It looked like it could be hot, I answered. There was a little preview and the tgirls are pretty convincing.
OK, you want to start with this one, then? And she walked to the DVD player and put it in.
We watched the first scene with studied indifference, as we usually, did. Picking apart the bad acting or obvious edits. The second scene began with a woman and her guy necking on the couch, moving to blowing him. Then she pulls away, and a stunning redhead walks in in lingerie. The guy and her begin kissing, and then she strips down, showing her dick.
You liking it so far, she asked, moving closer and putting a hand into my crotch. Sort of a ready-made lie detector, there. The rising bulge told her what she needed to know. She kept a hand there as I returned the favor, playing with each others bits as we watched the video. The scene had escalated to the redhead and the guy sucking each other, and then to the redhead entering him, as the blonde sat watching and fingering herself. It finished with the redhead cumming in his mouth, but I had turned away to take a drink, and missed it. She helpfully rewound it, then stopped to ask, You wanted to see her cum in his mouth?
I did, it looked hot, all right? I said, a little defensively.
OK, Just asking.
That night the sex was straight, mostly, but very intense. The next night, she put the same disc in again, to my surprise.
Thought you weren’t into it so much?
It’s growing on me, but can we try something different on the next videos?
What’s that?
Can we get something with 2 guys, you know… together?
Obviously, in the spirit of fairness, I had to pick one up for her. So the next time I went to the porn store, I found a bi 3some movie and brought it home. Up to this point, I was figuring it was mostly for her, and even though I liked girls with hard cocks, even watching them fuck guys and cum in or on them, this was not going to be my scene.
Turns out I was wrong. I just happen to have a thing for guys sucking cock, apparently. We put it in, and I don’t know which of us got fired up faster. That night, she strapped on a bigger dildo than we had used before, and I took it missionary style as she jacked me off onto my face and chest. I briefly considered licking some of it up, but chickened out before it happened.
Several months go by- things happen, we split up. Now single, and moved to a new city. Signed up for a dating site or 2 when I’m ready, but keep it very straitlaced. In the meantime, the fantasies and memories are creeping in around the edges, and I start getting curious again. Soon, I’m keeping shemale porn videos open in a background tab after work and just devouring hours of it, usually masturbating a few times as well. I also started playing with my ass again, buying a small plug, and keeping it for a while on the weekends while watching videos.
Eventually, I sign up for an adult “dating site,” figuring on looking for hookups or people into the same taboo play I am. Being a single guy, I uploaded the obligatory dick shot, as well as a few others where you could see the rest of me. I talked to a few women, and decided to take the bold step of putting that I was looking for TS/TV partners as well. That is, I learned, the kiss of death for most women’s interest. I saw my messages drop off and views from women dwindled. But, views from guys and from trans girls started increasing. I started talking to a CD from just south of me, who was just getting back into things after a purge, and we hit it off. She had a few pieces of lingerie, but was looking for something more before we got together. We agreed to meet at a local adult store and do some shopping. I got there and waited in my car until there ws a knock at the window. A cute younger Asian boy with glasses and a backpack stood there, asking if I was looking for Kenzie. I certainly was, and we headed into the store together to find what we needed. He whispered shyly before we went in that he wanted to show me what he already had, and opened the backpack to show a red teddy and a long black wig. We agreed to some stockings and panties, and he’d pick up some makeup on the way back to his place.
I stopped for some beers and to give him prep time, and when I arrived, he texted and said to come in and go to the bedroom down in the basement. I did, sat at the desk and opened a beer, nervous as could be. Was this really going to happen? Did I want it to happen?
Soon, the door opened and it was the moment of truth. Where I had gone to the shop with a slender boy, standing in front of me was a sexy, waifish girl, in red lingerie and fishnets with heels. Long black hair reached past her shoulders, and her lips were a glossy red.
You like?
I responded by putting out a hand and pulling her onto my lap, running my hands over her body. We kissed for a few minutes, still groping like horny teenagers. I slid a hand down to the front of her panties, asking, Is this OK? She whispered her approval and I found myself touching another cock for the first time. It was softer than I thought it would be, not as in erect, but the feeling of it, I stroked for a minute or two, staring at it in fascination, than kneeled down and took a tentative lick of the head. It was a musky flavor, at once earthy and salty. I felt her swell against my tongue, and that was when I realized how much I liked this. It was amazing!
I stood up, kissing her again as we moved to the bed and began to take my clothes off. Naked, I slid her panties down and pushed her legs up. Exposing her hole, I dripped lube on it and onto my cock, and slid in. It had been years since I had done anal on the giving side, and the tightness and warmth were almost unbearable. I had to slow my strokes to keep it together, and as I did I leaned in and licked a pearly drop of precum off the tip of her dick. As I thrust in, my mouth filled with a gush from her cumming, and I lapped it down without thinking. Soon after, I felt the moment coming, and pumped my cum into her ass, out of breath and in a headspace I’d never felt before. We lay there, idly chatting and made plans to stay in touch for future meetings.
Source: reddit.com/r/gonewildstories/comments/7mol3u/how_i_got_where_i_am_mf_mm