[MF] First kinky experience with my girlfriend... [Role reversal] | 2016

Sooooo... the most pivotal moment in my sex life was definitely the time in my early twenties that my girlfriend started playing with my ass. We had been hooking up for a while and it was starting to turn from nothing more than a hot and heavy hookup to a serious relationship. We had really grown to trust each other over those couple of months.

On this particular night, we ended up back at her place after a date. We started making out in her bedroom and before I knew it, we were both naked and she was sitting on the edge of the bed, sucking my cock. She stopped for a minute, gave me a funny look, and said she wanted to ask me something... I said ok, and she said, "Please, pretty please, would you pick up my panties off the floor and bring them over to me?" I did it in a heartbeat. I wanted her to take me back in her mouth. But she wasn't done. "I know this is random, but would you maybe wear them for me while I finish you off? … I want to feel the lace covering your ass while I blow you. I'm so wet already just thinking about it." I hesitated for half a second, thought "fuck it," and slipped them on. Her eyes glinted. She loved getting her way. She took me back in her mouth like she promised, and before I knew it, she was slipping her hand under the panties to squeeze and caress my ass. Before long, she was letting her fingers lightly brush against my asshole. I shuddered. She could tell I liked it, and she started rubbing one finger up against my ass, pressing lightly. We hadn't done that before, but we had talked about it and she knew I was open to it. I didn't object, and she took it a little further. She got her finger nice and wet and slowly pushed it in up to the knuckle. My knees almost buckled. She was still sucking lightly on the head of my cock as she worked her finger in and out, slowly applying pressure to all the right places. Five minutes later and I was on cloud nine, dying to cum, but she slowly pulled her finger out without saying a word. She went back to just sucking me. As great as she was with her lips and tongue, I didn't think I'd be able to cum now without her in my ass. It just felt too fucking good to go without. I finally gave in and asked her to play with my ass again. She told me she wanted me to beg for it. Obviously this was her plan all along. "Please play with my ass again, baby," I said. She looked right into my eyes and said, "Make it worth my while." Seriously? I had no idea what she wanted from me, but I would do anything in that moment, and I told her as much. She had that glint in her eye again. "Grab that bag off the chair in the corner for me." I walked over and picked it up. It was heavier than it looked, and I got a little scared. She had clearly planned this. What was I getting myself into? I handed it over and she looked so excited. She pulled out a tiny black skirt and a little lacy bralette that matched the panties I was already wearing and said "you don't have to do anything you won't want to do, but if you want me to keep playing with your ass tonight, take these into the bathroom and get dressed for me." She was sweet, but firm, and I knew exactly what I had to do. Feeling her finger in my ass had honestly changed my world. Nothing had ever felt so good. I gave her a trusting look, grabbed the bag, turned on my heel, and headed straight for the bathroom. Now, I don't have a naturally feminine form. I’m not petite. I don't have slender shoulders and smooth skin. I have a hairy chest, wide shoulders, a narrow waist, hairy legs, and I'm about 6 feet tall. My cock was already rock hard and sticking out of the top of the panties. The skirt barely covered my cock, and I had chest hair poking out of the bralette every which way. Oddly enough, I felt so feminine in that moment. I was the farthest thing from passable, but I loved the power dynamic of it. I was totally and completely vulnerable with this girl. I nervously opened the door to head back into the bedroom. She was laying on the bed, face down, wiggling that big, perfect ass of hers in anticipation, wearing nothing but some black spandex panties I had never seen before. She turned her head at the sound of the door, and her jaw dropped when she saw me. I don't know what she expected, but she seemed more than pleased with the results. “Look at you. So sexy. Come over here and go down on me before I play with that ass again,” she all but demanded. As I slid onto the bed, she turned over and revealed the true purpose of these spandex panties: a slender, realistic looking dildo sticking out of a hole in the front. I stopped in my tracks, starting at the thing. I looked up at her, and she was so nervous. Clearly she wasn't sure how I would take this part. “Wanna give it a lick?” She asked, clearly unsure what my answer would be. Every step I had taken outside of my comfort zone that night had only made things hotter. Why not? If I was honest with myself, I had always been a little bit curious. I reached out to her fake cock, grabbed a hold, and leaned in to give it a tentative lick. I loved it. On my knees on the bed in front of her, in panties and a bra and skirt, serving her cock like that, I could feel my cock pulsing.

She ran her hands through my hair as I took the dildo in my mouth and began bobbing up and down. I held onto the base of it and pushed it against her clit to make her moan. My jaw started to get sore almost immediately, so I kept grinding the base of the dildo against her clit while I made a show of flicking my tongue over the head of her cock. I locked eyes with her and we were both in heaven, having stumbled onto something we both clearly loved. By then she was pushing her hips up against me urgently and I could tell she was really getting close. I kept my eyes locked with hers and I took as much of the cock into my mouth as I could while holding the base and grinding it in circular motions against her clit. I sucked that fake cock as enthusiastically ever, and pushed it against her as she let out a deep moan and gave herself over to a shuddering orgasm. She lay there for a moment, her head on a pillow, while I laid between her legs, still holding her fake cock in my hand. Then she opened her eyes, looked at me, and said, “That was incredible. Now it's your turn. Get on all fours for me so I can get at that ass.” She got behind me and started rubbing my asshole through my panties before slipping them down. I buried my head in a pillow as I felt her tongue find my ass. She licked softly around the outside for a minute while she stroked my cock under my skirt. As she began pushing her tongue into my ass, I couldn't help but moan into the pillow. I was getting my ass properly tongue fucked and loving every second of it. I was so turned on and so worked up, I needed her finger again. As I pushed back against her, she knew. She pulled her tongue away and pushed a finger deep into my ass, making me moan into the pillow again. I was in ecstasy. She milked my cock with one hand while she fucked my ass with the other. Then she slipped a second finger in and I felt so full. “Is that good, baby?” She asked, as she pushed two fingers in and out of my tight ass. “yes, I'm so close,” I managed to spit out. She picked up the pace, fucking my ass with her fingers faster and tightly gripping my cock in her other hand. Her fingers hit the perfect spot and I moaned and bucked and finally came so hard I swear I went blind for a minute. I collapsed in a sticky mess on the bed as she slowly pulled her fingers out of me and slid up behind me. She was the big spoon and I the little, and she held me. “That was incredible,” she whispered in my ear. She was pushing her hips against mine and I could feel the dildo slip between my cheeks. She put on her cutest little voice and said, “Maybe next time you can take my cock in your ass after I cum in your mouth…”