Turnabout is Fair Play Part 1

Disclaimer: The following is another TRUE account of several of my sexual experiences with my boyfriend over the past year, and contains adult content. Please don’t read if you are under 18! Otherwise enjoy!

I’ve been writing up my sexual experiences with my boyfriend over the past year. Like all the other stories, this is in fact true! Hey, I need something to do while I’m not in class!

I admit anal play felt strange and uncomfortable the first few times I tried it, but a lot of that was because the idea of it just never turned me on. I had never really wanted to try toys either, they just seemed to strange. However, I became more curious about them after watching some adult videos with my boyfriend, and seeing how kinky they could be. After looking up some information and seeing that there are women who actually love them, I decided to have my first truly kinky anal experience months ago (you can read about it in my account “Pushing My Boundaries,” which is on a lot of sites!). Since then, we’ve added anal and toy play to our sexual repertoire, indulging every couple of weeks. My boyfriend and I couldn’t be happier!

I can’t begin to say how much I’m turned on by the pure sexiness of knowing we’re a kinky couple (my girlfriends know a little bit of what we do, and as shocked as they were they couldn’t help being curious!). It’s so hot knowing that our sex is kinkier than most porn; it added new excitement to our love life. Not to mention, there is no pleasure like an orgasm with the yummy, full feeling of having something up your butt. I enjoyed it so much, that I even began to use my butt plug occasionally while masturbating (remember, masturbating is good for a relationship!). Sometimes my boyfriend would come over to find I had been “warming up,” so he could give me some good old-fashioned tushy teasing!

One day, while we were getting off together to a video, we noticed the woman started to eat out and play with the guy’s ass. We ignored it right about the time my boyfriend rolled on top of me and proceeded to pump my pussy and rub my wet clit until I came. His cock slid in and out of me, and I heard his balls slapping while the actors moaned in the background. We stared into each other’s eyes as he held my leg up, using it to penetrate my pussy as deep as he could. Once I came, he held put his hand around my throat and pounded me as hard as he could (I like a little bit of rough sex, nothing intense!) I moaned and gasped in pleasure until he pulled out and blew his load into my mouth. After a stellar performance, we kissed and went on with the day. However, I became curious later in the week. I loved the feeling of having my ass played with and fucked; it’s one of the most exquisite sensations ever. Could my boyfriend possibly like it?

Licking his butt had been something I started doing a couple of months ago, and more than once he’s shot hot cum all over my face while my tongue teased his tight ass. But never before had I thought about taking it further with him; it was a new idea, and I was honestly more curious than turned on. I’d heard of prostate stimulation, but it seemed just a little too kinky for me. It sounded exciting, but was I going too far? Nevertheless, I became more and more interested in it, and even looked to see what I could find online. After reading hundreds of how-to’s and posts from husbands and wives who swore by it, I decided it wouldn’t hurt to ask my boyfriend if that was something he’s interested in. He was surprised at first, and unsure if it was something he really wanted to do. Always in the spirit of exploring however, he said we could possibly take it slow.

After he had fucked me until I came hard, I laid him down and kissed my way down his body. I gave him particularly messy head, slobbering all over his hard cock, tickling his erogenous zones lightly as I worked. I felt it twitch as my soft lips wrapped around the tip each time I came up, and he jumped at the sensation of my fingers on his body. It then progressed to licking his ass, which I knew he loved. Once I could tell his ass was begging for more, I placed a well-lubed finger at his opening, while slowly sliding up and down his hard wet cock. I massaged it in slow soft circles, occasionally letting the tip slip in. He briefly tightened up, but relaxed with some more teasing; I could tell he was enjoying it. When he was ready, I slowly let my finger slide in. He breathed out a deep sigh of pleasure as I kept it still, slowly pumping his cock all the while. I started to lick his balls and the creases between his legs, continuing to give him slow delicious pleasure. I looked at him to make sure he wasn’t uncomfortable or in pain. I saw him bite his lip and moan. Each time I twisted my hand over his tip, he jolted and gasped with pleasure, while his ass tightened and pulsed (apparently the penis tip and the prostate are connected, so stimulating both is guaranteed pleasure!). I began to move my finger in long, slow strokes, kissing and nibbling on him.

My clit pulsed and my pussy got wet again, watching my boyfriend receive such a naughty pleasure from me. Even my ass became jealous, and I thought about quickly stopping to slide the plug up my butt while holding my vibrator against my clit. But this was about him; I wanted him to feel the amazing sensation of ass play. He clearly was enjoying it and I wanted to keep going until he came. I gradually sped up my left hand on his cock, letting my finger slide in and out in rhythm. His pleasure moans and twitches became involuntary, I was driving him wild. Having dated for several years, I can always tell when he’s getting close to coming. All my research said the strongest orgasm a man can have usually involves his prostate being stimulated. I put my mouth over the tip of his cock, licking and sucking it as pre-cum oozed out. My finger was deep in his hot ass, stroking his prostate in a come hither motion. As I sucked and slurped, I looked to see him bucking uncontrollably. He groaned loudly, and I felt his ass tighten up incredibly. His cock pulsed and I began sucking harder and harder. Hot cum shot into my mouth as he squirmed in complete bliss, my finger still milking his prostate so I could taste every last drop.

My boyfriend laid in a complete stupor, his mind blown by what he later called one of the strongest orgasms in his life. That didn’t stop me from straddling his face with my wet pussy and telling him to thank me. He licked and sucked my clit, reaching back to massage my ass just how he knew I wanted it. Thinking of what I just did to him, I only took minutes to come.

My boyfriend was completely sold, and we would occasionally play with his butt, even working up to two fingers. He loved the stimulation, and knowing that his kinky girlfriend got off on pleasing him that way. It was hot for us to be able to share anal pleasure with each other, knowing (hoping) we were one of only a few couples who were kinky enough to do it. Sometimes he’d hint that he wanted it, sliding my hand down his back while he touched me. Other times, I would walk up behind him, squeezing his ass and licking my lips in his ear to let him know what I wanted.

Watching him cum hard and uncontrollably each time I played with his butt made me want him to do that while he was inside me. I wanted to feel him spasm against my body while my pussy was full of his hard cock. But I could only tease the outside during sex, and I couldn’t help but stop while I was coming. Then I thought, with a butt toy, he would be able to fuck me in any position we wanted, and still get that prostate stimulation that would make him come so hard. I thought about my first experience with the butt plug, how we took the evening to get into it. It was so hot and kinky; I couldn’t help but want him to have the same experience. But what if he thought it was too weird?

I was nervous; it was something I remained quietly curious about for weeks. I didn’t want to look like a huge weirdo, but I really thought it could be fun for us to try. We’ve been dating for a few years, we weren’t some old couple with a struggling sex life. Still, it makes both of us happy to experiment with sex. I figured with a little persuasion, my sweety would let me get him his own anal toy. After all, if my butt was good enough for one, his was too!

One night while we were laying in bed after he fucked me with my plug in, I thought long and hard (pun intended), and I asked him if he would ever be interested in possibly using one.

“Umm… I’m not sure…” he said.

I mentioned how he would be able to fuck me while it was in, and how much it would turn me on to know how kinky he was being while he railed me. I told him how I read online that anal play for men is becoming common for couples looking to spice up their sex life (not that we needed to). Not to mention, I told him how wonderful it feels to have a plug in. After all, I knew from experience.

“Think about it,” I sexily whispered into his ear while grabbing his soft cock and reaching under him to fondle his sexy ass, “Think about how much I love you teasing my ass with the plug, circling my ass and filling me up.” I let go of his cock and moved his hand under the sheet so he could grab the base of the plug which was still nestled nicely between my cheeks. “Think about how good it feels when I finger and blow you, and you can show me by fucking me hard. Think how wet your kinky girlfriend will be, knowing how hard you’re going to cum inside her.” As silly and awkward as I thought my persuasion was, I knew right then I was beginning to convince him; I felt pre-cum dribbling onto my wrist as I tweaked his tush with my fingers. “Pretty please…” I begged, having him rub my toy while I teased him, “… with a cherry on top?” I licked my lips, watching his body jump as I massaged his hot ass.

He laid on his back as I got on my hands and knees, feeling the soft wonderful toy inside my butt. I grinned at him while shaking my derriere in his face, letting him see how hot it felt to have my ass stuffed, hoping to make him jealous. With that, I took his whole cock into my mouth and fingered his ass. With my free hand, I began to rub the base of my plug, each rotation teasing my g-spot and making my body tingle. “Mmmmmmmm,” I moaned, letting my mouth vibrate on his cock. He grunted as I worked his shaft with my lips, and I had two fingers nicely teasing his ass. His cock kept throbbing in my mouth, twitching as my fingers stroked his prostate. I could hear him gasping, and feel him squirming underneath me. Like the considerate lover he is, he reached between my legs and started rubbing my soaking wet clit. I moaned with approval, and slowly removed the plug part way. I wanted him to see my tight butt hole around the toy, like the girls do in porn.

“That’s so fucking hot,” he said, seeing my horny ass around the purple toy, with my wet pussy right below it. However, the sensation brought me close to the edge; I felt the most amazing stretch as my tushy gripped the widest part. “Oh fuck…” I whined in pleasure after taking my mouth off of his cock. I started to stroke up the shaft, twisting over the tip and back down, making him spasm the way I love. I was so horny, the plug actually popped out! I squealed and laughed at the sudden surprise, but then said in my sexy whine “Baby, please put that back in my ass, sloooooooowly.” He was too busy gasping in pleasure to answer, but followed my orders. I shook his target up and down, and could feel the plug rubbing at my entry. I was so fucking horny and it opened right up. “Don’t put it in all the way, fuck me with it baby.” He slid the wide part in and out just a little bit, and it felt like his cock giving me the hottest stretch. “Oh fuck… Fuck yes… Fuck me baby… Fuck my naughty ass.” My whole pelvic region was tingling with pleasure, his fingers rubbing my clit and making my knees week while my horny ass radiated joy to the rest of my body. I was so close to coming, it was time to seal the deal. Faster and faster my hand slid over his cock, and I moaned “Baby please let me toy with your hot ass, it’ll feel so fucking good,” I teased. He moaned and grunted as his cock began to pulse. “Please let me do it, I want you to cum so fucking hard while I toy with your ass, I want you to fuck me hard with a toy in your ass…” At those words his ass tightened up and a fountain of cum shot out of his cock. He slowed down only a little, but promptly went back to pleasuring me. “Keep going,” I whined, as my body began to tremble. My horny ass sucked the plug in up to the base, making me shudder with pleasure. My boyfriend rolled on top of me as I collapsed in ecstasy. He thrust his tongue into my mouth, rubbing my clit faster and faster. I moaned and whined out against his mouth as I began to come, my ass squeezing the toy harder than I thought possible; it felt so fucking hot. His weight on top of me, he began licking and sucking my neck and I came so fucking hard. I could do nothing to move or escape the pleasure; I was his prisoner of love.

We both lay there sweating, dazed from the sex hurricane we both just experienced. After collecting myself, I walked towards the bathroom to shower, but not before I bent over and let my sweety see me ease the toy out of my ass. It came out with a pleasant pop, to which I gave a cute “Ooo!” My boyfriend laughed and turned over, and I knew he was game. The whole time in the shower, I was excited just thinking about what my boyfriend had just agreed to. I smiled to myself, marveling at how only a year ago, I only liked vanilla sex. Funny how things change!

That weekend, we both went to the Babeland store in SoHo where I bought my plug and vibrator earlier in the year. It clearly wasn’t what my boyfriend expected from an adult store. “So the creepy men in raincoats… where are they?” He jested. I giggled and we kept walking around the store. For anyone who doesn’t know about Babeland, it’s a pretty nice place run entirely by women who are all about being sex positive. One of my girlfriends recommended it to me as the place she gets her vibes from.

As we shopped I looked up, expecting to see either a saleswoman or a customer surprised by the sight of my boyfriend and me (who is as manly looking as they come) in the butt toy section. To my surprise, nobody even raised an eyebrow. We weren’t even the only couple looking there (albeit the others seemed much more familiar with it)! We looked for a while, my boyfriend had no idea what would be best to get. I noticed one of the saleswomen, a cute girl with short hair, restocking the shelf.

“Can I help you with anything?” she cheerily asked, having noticed I was looking at her.

I shyly told her we were interested in purchasing a butt toy my boyfriend could use and be comfortable with, but were not sure what would be best.

Sensing we were timid, she told us how over the past few years, most of the butt toys Babeland sold were to heterosexual couples interested in turnabout. “We love it here when straight men explore butt sex!, it keeps us in business!” she exclaimed. She then proceeded to show us the most popular toys. One toy, the Aneros, was designed by doctors as a way to prevent prostate cancer but ended up working great as a sex toy as well. In fact, she said all butt play reduces the risk of prostate cancer in men (can you say hot and healthy?!).

After going through several toys, she told us about one called the Tristan. It’s named after a famous sex educator who specializes in anal play, and comes in a beautiful purple (like my plug back home), as well as a much manlier black (much more fitting for my sweetheart). I just pictured seeing that nestled inside my kinky stud, and my felt my clit pulse a little. The saleswoman explained how it is big enough to give a pleasurable full sensation, but just right for a beginner, with the base designed to fit comfortably between the cheeks! She even told us how both her and her husband love the Tristan. Thoroughly convinced (and secretly turned on), we went ahead and purchased it.

We held hands on the way out, both excited by our new purchase. We giggled about how we were officially a couple who went sex shopping together. It wasn’t hot so much as it was nice; here we were on a beautiful Saturday in April, exploring sexuality with each other. It really is a big part of love to be able to be so open with each other, truly believing there is no shame in pleasure with each other. With the toy in my purse, we spent the rest of the day in Central Park, and even had a lovely dinner to cap off the day.

Sorry, I always have to throw something mushy in at the end! Relationships aren’t all about sex after all! I’ll post part two once we try it!

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