[FM] His First Anal Experience

I have my partner, my dom, and my paramour. My paramour is 11 years younger than the other two, and he has led a very conservative life due to his rigid upbringing. He met me, an almost insatiable, sex-positive polyamorous woman who needed one more outlet for my immense sexual drive and natural affection.

We had hoped to see each other this past Saturday, but he had a family emergency that night and had to cancel at the last minute. We had been anticipating the evening all week, thus after the missed opportunity, we were ravenous with the need to see one another soon. The hunger was palpable by Monday evening, and we knew we couldn’t wait any longer to kiss each other again. As he text me, he mentioned that he had been having dirty thoughts about me over dinner. I asked him to be more specific, and he told me about how he had been thinking of me showing up with my purple butt plug inside my ass and using my glass dildo on my pussy before fucking my ass. He had never been with a girl willing to do anal, and I personally love it (when done right), so I had already planned on removing that To-Do item from his list one day. I told him I was going to get ready to see him, and we stopped texting as I prepared.

I laid out my thigh-high fishnet stockings, my short black skirt, my blush pink demi-bra, and my see-through black silk shirt. I took my time making sure I was nice and clean and ready for a cock up my ass. I squirted some lube into my tight asshole before sliding my purple butt plug inside. It’s a very flexible silicone plug in a beginner size, so it’s comfortable to wear for an extended time, and it mostly moves with me. I pulled up my thigh-highs, leaving my freshly shaved pussy and firm ass uncovered underneath my black skirt. I pulled the blouse on over my pink bra, and I made sure to unbutton the blouse all the way to the beginning of my cleavage. I zipped up my tall black boots and rubbed some lavender oil on my pulse points and tips of my hair before heading out the door.

I know of a quiet formal garden that is tucked away in the middle of a campus. It is mostly dark at night with just enough periphery lighting around the grassy terrace that one can barely see the lush grass at their feet. He meets me at the garden, and we sprawl out some large black silk tablecloths that I have for work as a blanket and ball up some others for makeshift pillows. I unzip my tall boots to reveal my fishnet-clad legs, and we sit upon the linen. I opened a bottle of tasty pinot noir and we take turns sipping from the long neck of the bottle as we talk about our day, I make sure to graze his hand with mine each time he passes it back. I can’t keep my hands off him, and run my nails lightly over his arm and underneath his shirt as I move closer to him. He had a stressful weekend with the family emergency and is letting off some steam while all I can think of is easing his mind by running my tongue over his firm stomach. I settle for using my fingernails as we lie down, and I snuggle my face under his chin and against his chest, my soft pink, lavender-scented hair falling around him.

His hands soon begin to run over me as mine continue their delicate exploration of his body underneath his shirt. I lift my head up to kiss him…one kiss melts and blends into several as my hands move up to his face and neck and caress him gently as I savor the softness of his tongue against mine.

I use my other hand to gently slide my silk blouse over my breasts as the ambient garden light softly illuminated the curves of my body. He slid the lace fabric of my bra down and gently swirled his tongue slowly around my nipple as my body relaxed completely underneath his warm touch and tongue. I ran my hand through his hair and pulled him closer to my bosom as my back arched, and he responded with a firmer nibble and flick of the tongue. Instinctively, my legs softly parted.

As I lie on my back, he moved his body down between my thighs and pulled up my skirt to reveal my bare pussy framed by the red lace of my thigh-highs. I heard him gasp slightly as his eyes made out the end of my purple butt plug in the dim garden light. His tongue was soon gently examining the thoroughness of my shave job as I softly moaned, and I decided that now was the time to show him that I had listened to his fantasy. While his face was buried, I slyly reached my hand into my nearby purse, removed my glass dildo, squirted some lube on it, and slid it down to his hand that was resting on my firm thigh. “Here, I believe you mentioned you wanted to use this…..” He gasped again.

I spread my legs wider as he slid the head of my dildo gently into my pussy. I could feel the squeeze of the butt plug against this extra pressure. It became difficult to suppress my moans to an acceptable level that wouldn’t alert any nearby college students who use the garden as a shortcut to their dorms when returning from the bars. But curious college students were an insignificant concern to us at this point, as he began making me cum and my gentle, rolling multiples took over.

After about five multiples, I was sufficiently relaxed and submissive and ready for anything he wanted to do to me and the immense pleasure he would give me. He moved his body to spoon me and covered us up with an extra linen to help disguise us from nosy coeds. I soon felt his hard cock pressing against my ass cheeks.

I reached down between us to remove the butt plug, then I lined the head of his cock up with my tight asshole. As we spooned, I gently pushed myself slowly back onto him, feeling the head of his cock start to push inside me. The butt plus had warmed me up nicely, and it was a very pleasurable and easy experience. I moved as slowly as I could mainly for his own pleasure and experience as this was the first time he had ever experienced anal sex. When I finally pushed back for maximum depth, I also pressed my body backwards against his and pushed my head underneath his own so that his lips were against my ear and his head was resting on my soft hair as he began slowly sliding inside of me. My moans began to join his rhythm and his own moans of pleasure. I twisted my back a little more and turned my head to softly kiss his lips as his hard dick moved inside me. I was expecting him to want to fill my ass up immediately, but he soon moaned into my ear, “Your ass feels amazing, but I would love to fill your pussy so much right now, and then I will fill that ass before we leave.” Normally I wouldn’t allow the switch, but I had been so thorough in my cleaning and prep that I had no issue with the idea this time. I moaned back, “Yes, please, I would love your warm cum dripping out of both of my holes.” This sent him into a frenzy, and he slid out of my ass and deep into my pussy. As we continued in the spooning position, I moved onto my elbows so I could push back and bounce against his thrusts. Soon I was cumming as I squeezed my pelvic muscles to feel his thickness inside me. He moaned deeply, and I felt the pulsating warmth filling me up. We collapsed together in our tight spooning position, panting as our heart rates lowered, and my body trembling and gyrating gently against his as I came down from the aftershocks of my multiples.

We cuddled and talked and enjoyed more wine under the moonlight. We cursed the time over and over again and struggled to break off our conversation for another session before we had to part ways. It was 2 AM on a worknight, and both of us would have been happy to be found in the garden at sunrise if we didn’t have such hectic jobs. My hands and lips never ceased grazing his skin, however, and soon we were back to spooning under the stars as I reached my hand down to locate my glass dildo and began to play with myself.

He held my body closely as I let myself relax and made myself cum for him. Soon his hard cock was once again pressing against my tight ass, and again I pushed back against him. This time, I left the glass dildo inside my pussy, and the feeling of him sliding inside my ass was intense in the most enjoyable way. He moaned as I began to slowly slide the dildo, and he remarked on the amazing sensation he could feel through the double penetration. I slid the dildo into a comfortable position and let it stay inside me as I moved my hand back to grasp his hip and one hand to steady me as I very gently and slightly bounced backwards against him. I delicately rotated my hips during the slow thrusts, and soon our bodies were pressed tightly against one another as we gave way to the orgasm. His cum filled my ass, as I pushed my head under his and felt his warm breath against my ear. And there we stayed for a bit, as close as we could be, catching our breath and softly moaning to one another as his cock slowly relaxed and eventually slid gently out of my ass.

I rolled over to kiss him tenderly and asked him how his first anal experience was. “Amazing….”

Source: reddit.com/r/gonewildstories/comments/9lmzpk/fm_his_first_anal_experience