[FM] My boyfriend finally agreed to try anal play…on him

My boyfriend and I have always been open-minded. We aren’t each other’s first sexual partners (far from it in fact), but we have achieved a lot of firsts together – first public sex, first group sex, first extensive bondage, etc. I could potentially be convinced to write up these stories another time. Who knows? We’ll see. But, without a doubt, the biggest, sexiest first for us was the first time I played with his ass.

For some background on us, we were in our mid-twenties and had been together about six months when this finally happened. Pegging and anal play had been a joke between us for so long that I didn’t think it would ever actually happen. We even joked about it the first time we had sex; we had talked about Broad City earlier in the evening, and when we changed positions I joked that I was going to peg him like in one episode. From then on it was almost a meme. We’d be lounging around on a weekend morning and he’d ask what I wanted to do that day and I’d say “oh wasn’t I supposed to peg you today?” or “oh my gosh I totally forgot that I have an appointment to peg you raw.” I never actually expected it to go anywhere.

My boyfriend, let’s call him Henry, found these jokes absolutely fucking hilarious. On the days he laughed a little too hard, I would put on an exaggerated English accent and say “methinks m’lord doth protest too much.” He would always roll his eyes and then tackle me and pound me into the bed to “prove” he thought it was a joke. I found out later that he was always rock hard during those fuck sections because he was thinking about me pegging him.

It all came to a head (terrible pun not intended) one night when we got a little twirly on G&Ts and two player drinking games. Which are basically any drinking games turned into an excuse for a couple to get wasted and fuck. I was sipping on my third or fourth G&T and kept licking and sliding my tongue around the straw (metal obviously, I’m not a monster) as if it were a penis. You know, the height of comedy and seduction. At one point I picked up the straw and slid it partway down my throat. Henry did his adorable stupid little snort laugh that he does whenever he’s trying to laugh off being turned on. “You’re getting off on this,” I said, letting some of the drink slide down my chin.

Henry rolled his eyes, but I could tell he had to shift to adjust himself under the table. “You aren’t all that, you know.”

“Oh?” I asked innocently, using the straw to drip liquid down my neck and into my ample cleavage, “So this does nothing for you?”

“Absolutely nothing,” he said, his eyes following my movements and his tongue peeking out to wet his lips.

“Then you won’t mind if instead of sucking your cock I……..PEG the ever loving FUCK out of you?” I took the straw and held it at my pelvis like a dick, thrusting at the air and making a dumb face at him.

Henry, as drunk and silly as I was, got up and stood behind his chair, bending over and leaning on it to stick out his ass. He has an absolutely incredible ass. The kind of donk you need a killer combination of genetics and daily squats to achieve. I got up behind him and jokingly thrusted against him with my metal straw penis, lowering my voice to a hoarse whisper. “Ah yeah you like that don’t you? You like me fucking you with my long, fake cock?”

Henry responded in a silly voice at least a full octave higher than his regular speaking voice. “Oh baby! Fuck me raw with your straw!”

We kept giggling, and I kept thrusting against him. He stayed bent over but turned his head slightly to the right so that I could kiss him while I “fucked” him. What started as a joking sloppy make out interspersed with “oh yeah baby fuck me harder” and “your asshole is so tight” in funny voices eventually turned sincere as we deepened the kisses. I took advantage of his submissive position to lean into my rarely-seen dominant side, sucking on his bottom lip and biting down harder than my usual soft nibbles.

At some point the metal straw clattered to the floor while we kissed, but I didn’t stop thrusting against him. I don’t know why. Maybe inertia? Maybe I just found it hot to drunkenly slam against him while we made out. I gripped his hips, thrusting progressively harder against his perfect ass and panting into our kisses. Henry reached his right hand behind himself to grab my arm as I fake fucked him, his ass almost involuntarily pushing back to meet my thrusts. I kept my right hand gripping his hip and slowly slid my left hand up his back to hold onto his left shoulder. Henry broke our kissing to bend down farther over the chair, letting out a slow groan as he did.

I’m not sure how long we stood like that, me non-jokingly humping my boyfriends ass while we bent over my kitchen chair, but I knew I had to progress it or stop it. I slowed my thrusting to a grind and brought my right hand around to dip below the waistband of his sweatpants. I could tell his pants were stretched tight from his rock hard cock before my fingers even found the proof of his erection. Eventually I was able to grab his dick and start slowly tugging on it while grinding my now dripping pussy against his firm ass. Henry’s soft groans became more frequent. Peppering kisses down his back and pressing my tits against him, I spread my legs slightly and angled my pussy so that I could stimulate my clit with each up and down rub against his ass.

I used my thumb to spread Henry’s precum around the tip of his cock, his body bucking against me while I played with his sensitive head. I couldn’t believe how turned on I was. “Henry,” I whispered, not wanting to break our trance, “I really want to fuck you.”

“Please,” he whispered back.

I am not a naturally dominant person. But when my sexy boyfriend whisper-begged for us to fuck, I nearly orgasmed right then and there. I took my hand out of his pants and spun him around to face me. Looking back, I would have thought that my ability to be dominant would be slightly hindered by his height, but I forcefully grabbed a fistful of his shirt and brought him down to meet my lips. His hands wandered around my waist to cup my ass, pulling himself against me as I stood firm on the spot. I kept one hand holding onto his shirt and snaked my other hand into his hair to pull it slightly. Henry moaned into my mouth.

We stumbled into the bedroom blindly, trying not to trip over anything but not willing to separate from our frantic kissing. I gruffly licked and bit my way down his neck, using the hand tangled in his hair to pull him down to a manageable height. Henry’s hands roamed my body, first cupping my ass then dragging one long finger along my pussy lips over my shorts then squeezing my tits under my t-shirt and tweaking my nipples. Our moans and heavy panting filled the air. I felt the backs of his knees hit the bed and broke our kissing to look him directly in the eyes. “I don’t want you to do anything you wouldn’t do sober,” I said, using both hands to cup his face and force him to look at me, “I want this, but only if you want this.”

Henry was still panting, his lips swollen and hair disheveled. “I want this. Please.”

I swear I felt myself get wetter. “Tell me what you want, Henry.”

He looked down, his hands shyly playing with the bottom of my shirt and drifting across the soft skin of my stomach as he swallowed, building up his courage. Still not meeting my eyes, he said, “I want you to play with my ass. I might change my mind during if I don’t like it, but I want to try.”

I stood on my tiptoes to kiss him softly, sweetly, before deepening the kiss to regain our hot, frantic energy from earlier. I pushed him down on the bed lightly, enjoying the fact that he was suddenly shorter than me and I could take a dominant stance. Henry’s hands tangled into my hair as we kissed, his fingers massaging my scalp slightly. I reached down and spread his legs so that I could stand between them. He helped pull off my shirt, my nipples hardening even more as they were exposed to the air. I leaned my head back and sighed as he dipped his head to lick, suck, and scrape his teeth against my nipples. One of his hands snaked down the front of my shorts, slowly circling my clit with one finger. My panting turned into moaning. I leaned my forehead down against his as he put more and more pressure on my clit. “Don’t fucking stop,” I whisper moaned.

Henry turned his face up to kiss me, slowly penetrating my mouth with his tongue. At the same time, he finally pressed two fingers into my wet cunt. “Fuck, Henry.”

He smiled into our kiss, and used his other hand to slide my shorts down and let me step out of them. He resumed fucking me with his fingers and using his thumb to apply pressure to my clit. It wasn’t long before I felt an orgasm building in my lower stomach. I started bucking against his hand. My moaning got louder. Finally, I felt myself reach the edge of the precipice and fall over, cumming hard against his fingers.

Henry brought his hand up to his mouth to lick his fingers, but I grabbed his arm to stop him. Slowly, and maintaining eye contact, I licked up the length of his fingers before pulling them into my mouth and sucking hard. His eyes darkened, and his mouth opened slightly. Breathing hard, Henry used his other hand to pull down his sweatpants. I released his fingers and swiftly pulled his shirt off over his head. “Are you ready?” I asked.

Henry nodded.

“I need you to say it, Henry.”

I saw him swallow, and his voice was low and husky when he finally repeated his words from earlier. “I want you to play with my ass.”

A grin quickly spread across my face as I adjusted us more fully onto the bed. Henry’s head lay against the soft headboard, and he spread his legs so I could kneel between them. I leaned down to kiss him deeply again, catching his bottom lip between my teeth and biting down on it roughly as I pulled away. I kissed, licked, and bit my way down his body, pausing to pay special attention to his hipbones. He bucked against me, my ticklish bites visibly making his cock twitch. I continued to tease him, moving my mouth around the base of his cock but never quite touching it. My hands travelled up and down his thighs, the dual purpose of holding myself up for balance and massaging him. I glanced up at Henry – his eyes were closed and he was breathing heavily through his slightly open mouth. After one final pass up and down his hips with my lips and tongue, I finally took his cock into my mouth.

Henry let out a low groan, my name falling from his lips. I opened my mouth wider and relaxed, taking him deeper and deeper until he bottomed out in my throat. He thrust slightly against me, but I pushed his hips down as a warning. I released his cock with a slight suction noise. “Do that again and I won’t let you cum.”

He nodded, eyes still closed and balling the sheets in his fists. I resumed sucking his cock slowly, using one hand to prop myself up and the other hand to grip the base of his dick. My hand and my mouth started working together to suck and tug him, getting sloppier and wilder as Henry’s encouraging groans got louder and more frequent. Eventually I lubricated his cock enough to jerk him with my hand and let my mouth wander. I kissed down the length of his cock until I got to his balls, sucking one into my mouth. I gently sucked and licked each of his balls, using my right hand to continue stroking his dick. Henry opened his legs wider and adjusted so that his cheeks opened slightly and his pelvis was tilted upwards. He looked down for the first time since I had started sucking him and made eye contact with me. He nodded.

Emboldened, I licked my way below his balls until I reached his asshole. I trusted him to be clean, and I figured I should try licking him the way I like having my pussy hole licked to see what he liked. I used my left hand to spread his cheeks more and then took one long, slow lick from his asshole to his balls. Henry let out a long, low moan filled with expletives. He placed his feet flat on the bed and lifted his pelvis to provide me with easier access, and I took the opportunity to dive in. My tongue aggressively circled his asshole as my right hand continued to rhythmically pump his cock. Finally, I stuck my tongue directly in his tight hole and swirled it around the edges. He couldn’t stop himself – he started thrusting into my pumps and grinding his ass against my face. I could feel myself getting more and more turned on as I brought him pleasure. There is nothing sexier than making a man unravel at your touch, knowing that you were the one to make him feel that way.

Eventually the angle got a little uncomfortable for my neck, and I knew we would have to adjust. I reluctantly tore myself away from Henry’s ass long enough to tell him to turn over. Like the good boy he is, he quickly obliged and moved on his knees into essentially a doggy-style receiving position. Muuuuch better. I used both hands to grip his ass, and I saw his right hand move down to tug at his cock while I got into position. Without warning, I dove my tongue right back into his asshole. Henry let out a gasping moan from the surprise and the sensation. I was quickly becoming addicted to making him feel so good. Keeping my left hand gripping his round ass, I removed my mouth and moved my right hand to his soaking wet hole. I slowly circled the rim with the pad of my thumb and took a breather. “Can I finger you?”

Henry let out a strangled “fuck yes” from up where his face was pressed into the bed.

I took my pointer finger into my mouth to wet it more before bringing it down to slowly stroke up and down over his asshole. Henry’s movements jerking his cock got tougher and wilder from underneath us. I slowly, carefully, inserted my finger. Henry groaned and stilled his own movements. I paused, leaving my finger inside him to let him adjust. “Is this ok?”

I could see him nod. “It’s weird. Good. Hang on.”

I sat up to kiss his back and rubbed his skin gently with my left hand. Slowly, he exhaled. “Ok keep going.”

Henry resumed his own movements, slowly stroking up and down the length of his cock. I pushed my finger slightly down towards the front of his pelvis, feeling for his prostate. I finally found a small bulb and pressed down and forward against it. “Oh my FUCKING god,” Henry said at normal speaking volume, “Keep doing that don’t fucking stop doing that.”

I continued pressing against that spot, moving my finger in an upside down come hither motion. Henry’s groans got louder and his movements became frantic again. I removed my hand briefly to lubricate my pointer and middle finger. I thought about putting them in my mouth but instead stroked my pussy to gather some of my own wetness. I moaned, staring at Henry’s spread cheeks and glistening asshole and taking the opportunity to circle my clit a couple times. Gently, I brought my fingers back to his ass and inserted them slowly, letting him get used to the presence of an additional finger.

“Yessssss fuck,” he groaned.

I resumed my fingering, and Henry started pushing back against my hand. I rotated my arm and angled my body to provide room for my mouth. Relentlessly, punishingly, I fucked his ass with my fingers and licked and sucked his balls from behind. Henry’s moans, usually so soft and low and deep, got uncharacteristically loud and higher pitched. “Fuck fuck fuck I’m close don’t stop.”

I was dripping wet. Henry was so fucking sexy – the man usually took the lead in the bedroom, so having him bent over and spread in front of me at the mercy of my fingers and tongue was the hottest thing I had ever seen. I kept up the pressure on his prostate with my fingers and sucked one of his balls fully into my mouth. Henry groaned out my name as cum spurted from his cock, his frantic movements and violent orgasm spraying it all over the bedspread. As the last spurts ended and he ceased his own pumping, I slowly removed my fingers from his ass and released his ball from my mouth. Exhausted, Henry collapsed onto the bed, not even caring that he was laying in the wet spot.

I kissed my way across his perfect ass cheeks and rubbed his thighs with my palms. His breathing finally began to calm down while I kissed my way up his back. When I reached his shoulders, he slowly turned so that he could face me. Suddenly somewhat shy, I bit my lip and softly stroked his arm as we rested on our sides facing each other. Henry finally raised one hand to cup my cheek and bring my face to his. We kissed slowly and gently, inching our naked, exhausted bodies together. By the time we ended the kiss, he was holding me in his arms and stroking my hair, my top leg resting around his hip.

Too exhausted to do anything more, we slowly ground against each other. I had never felt closer to him. Henry kissed along my jaw and scraped his teeth against my ear. “I want you to cum for me one more time.”

I was so turned on from the night’s events and so sensitive from my orgasm earlier in the evening that I knew it wouldn’t take long for me to finish. He pulled me even tighter to him as he rocked against me, using his hip and thigh to grind rhythmically against my clit. In a matter of seconds I was cumming and calling his name into his shoulder as he kissed my neck. I willed my racing heartbeat to calm down and kissed Henry between panting breaths. “That was amazing,” he said after a moment of quiet contentment.

“No regrets?”

He laughed a genuine, throaty laugh and pressed his lips to my forehead. “Not a single fucking one.”

I sighed contentedly and turned so that we could spoon. “I fucking told you.”

In the morning, slightly hungover and sore but verrrrry happy, we ordered some tools and toys online so that we could continue our exploration of Henry’s ass. The pegging jokes continued, of course, but they were always made with a smug, knowing smirk, the image of our newly-purchased strap-on tucked away in my bedside table floating to the forefront of our minds.

Source: reddit.com/r/gonewildstories/comments/gpjwrx/fm_my_boyfriend_finally_agreed_to_try_anal_playon