πŸ“š first time with a man Part 11 of 5
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First Time With A Man 11

First Time With A Man 11

by lustyisser
20 min read
4.67 (22500 views)
adultfiction
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First Moment of Love Making

I don't know how I had turned bicurious. But those were the days of singledom. I was living and working in isolation. Most of my days would be spent working on my computer alone in my office and I would browse the personals section on craigslist. Initially I started replying to F4M section. But I rarely received a reply back and those that replied were scammers and prostitutes.

I slowly transitioned to reading M4M ads and got hooked. I guess I always had some bicurious tendencies growing up and this became an outlet for my boredom. I was fascinated by the big cocks that some guys would put up in their ads. Equally alluring were inviting images of men on their knees, their back arched seductively, and their smooth asses in a lewd display. What excited me most were posts of masculine men with wide muscular chests and thick hanging cocks. I tried replying to some of them but I guess my language didn't appeal to them.

So, taking advantage of my vivid imagination, I decided to post my own ad where I declared my desire to have a masculine man make me feel like a woman. I received many replies but it was an Indian guy who wrote a detailed reply of how he would seduce me. I was floored by his imagination and also enticed that he was a fellow Indian. My reply to him was equally seductive and he was excited to find out that I was also Indian. We'd exchanged a few emails sharing our fantasies and in a moment of boldness I shared my phone number with him. He texted me immediately and we spoke later that night over the phone. It took a few attempts at setting up a meeting and cancelations since both of us were nervous and concerned about our privacy.

After a few missed chances of meeting outside, I decide to bite the bullet and invited Ameesh to my apartment for a meetup. I had a roommate and I was somewhat worried that he might come home anytime. Luckily, Ameesh was Indian so he could pass off as a friend. He came in and sat on the couch in my living room and we got to some courtesy small talk. While we were talking, he scooted close to me and gently took my hand over his. It was a surprise move that got me pleasantly surprised and nervous. He had romantically asserted his masculine role. In a moment of shyness, I said: "I am hungry. Can I make some omelet for you as well?", and walked over to the other side of the open plan living room where the kitchen was. He watched TV for a few minutes and I got started with the omelet.

While I was whisking the egg, he walked over behind me and put his hands on my waist. I was wearing loose pajamas and a T-shirt and the touch of his fingers on the bare skin of my waist was electrifying. My mind was distracted away from whisking the egg to the anticipation of what was to come. Every woman remembers their first time and this was that moment. His left fingers slid gently from the waist under my t-shirt into my pajamas and into my underwear. My pajamas and underwear got lowered a little and his fingers grazing through the sides to the upper portion of my ass. It was a treat in sensuality of the feminine experience that I still relish years later.

In that moment, he had moved close enough to rub his cock on my ass. I could feel his raging erection through the fabric. Like a master seducer, he brought his lips close to my ears. I could feel his breath on my ears and instinctively leaned my head back resting it against his chest but turned away from his lips. As I leaned back into him, I had a sense of security in that sensual moment feeling his whole body pressed against mine. He had seduced me and I was willing to be seduced. Taking his cue, he lowered his lips on the nape of my neck planting wet kisses downwards.

That moment of erotic surrender was an experience in feminine bliss. His large hands had made me naked by then, as he pressed his manhood on may naked ass. He continued going down and up my neck, planting lingering kisses as his left hand grabbed my butt cheek and pulled is further left prying the crack my ass. I could feel his manhood pushing deeper in the crack of my ass as a result of his ministrations. For a moment he stopped kissing my neck and started nibbling on my ear lobe. He had already freed his member from his pants somehow and I could feel that hot rod lodged vertically in the crack of my ass. It was a feeling like no other.

My own erection was pressed against the handle of the stove and my own hands were busy holding the cup and the fork. A perfect circumstance to feel the yin energy. My butt was pressed against his crotch while I had arched my back to lean my head against his chest. For a person looking from a distance, that embrace was a portrait to be painted. His finger moved from my butt to the side and came closer to my crotch. Instinctively, I jerked pushing him further back and got back to my senses. I don't know why I made that move but feel like I had the instinct to not let him feel me in the front just as yet. I got back from the blissful surrender to a moment of control where I told him that I need to finish making the omelet. He should wait for me on the couch.

My hands were trembling as he pulled away. A huge part of me didn't want him to move away. But he was a gentleman who knew the limits of a consensual encounter happening for the first time. That is something I still admire about him years later. I finished making one omelet and served it to him with a fork and sauce. There was shyness mixed with service in my demeanor that a feminine woman experiences in the initial phases of relationship. I was feeding my man before our encounter, as if I had a visceral understanding that a woman has to fill his stomach to arouse his libido. It wasn't the case here but I was somehow playing a woman's role too well.

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I went back into the kitchen and made an omelet for myself and went back to the couch. He was done by then and he welcomed me by patting the portion of couch right next to him. He was sitting at an angle in the corner of the couch and I sat next to him as we both stared at the TV while our minds were in a state of sexual tension. I ate my omelet in silence but that the same time, my right shoulder was pressed in to his chest and his right hand was gently stroking my shoulders.

As I finished my omelet, it leaned forward to place the plate on the table. I was conscious of my movements as I could feel his eyes ogling at my stretched form and especially my shapely butt lifted slightly from the couch. As I returned back to the couch, he swung is left hand on my left shoulder and pulled me into him. It was comforting to be in a semi embrace. It was my turn to seduce him and I turned to him and told him that my neck and shoulder hurt from working long hours I front of the computer.

He needed no further invitation, as he asked my turn around and has sideways on the couch away from him. I nervous got on my knees facing away from him as he got behind me while his chest was pressed against my back. He pressed his thumb right at the base of my neck right where the shoulder meets the neck. I just melted with relief as his firm hand gripped away at the physical and sexual tension in my body. I just had to follow his lead now. For the first time in my life, I was enjoying the receptive role of a sexual union. Being led with a firm hand is a feeling like no other. It makes you feel secure and complete beyond the sexual touch and I had the opportunity to feel it first-hand.

He continued massaging my back as his fingers slid down my spine in measured motions generating tantalizing sensations all over my body. His fingers stopped at the rim of my pajamas and his fingers grazed sideways. Before I realized, he lowered the lose elastic band on swift motion and a sign was all I could muster. He pushed me to lean a little forward as he lowered my pajamas and underwear hallway down my thighs. I felt so vulnerable being exposed fully to his probing eyes.

Leaning forward supporting my body on my hands, I was enjoying the feel of his hands stroking and caressing my naked butt. He has already seen pics of my smooth butt but this was an erotic sight for him. For a man to be fully exposed and available for the sensual pleasure for another man is not what nature had probably intended. But here I was, giving another man an erotic viewing pleasure of a smooth posterior, available for him to do whatever he wants to do with it.

Nothing is more feminine than giving that control and pleasure to the masculine, to be at his whim, feeling pleasure in whatever way he wants to feast on your body. Nothing is more sensual to a woman than feeling powerless in the sexual union. I was in that state of mind. His hands were squeezing my tight ass, gently stroking and spanking my cheeks. With both his hands on my checks he pried them apart stretching my bud. While I sighed at his maneuvers, I could feel the trembling in his fingers as they grazed my puckered hole.

He placed one hand on my shoulders and pulled me up. He lifted my hands and pulled my t-shirt in one go. He leaned forward and planted a kiss on my back as I was arched backwards. Shiver ran down my body as I threw my head back to that electric sensation. My shoulders found support of his chest as his face nuzzled at the nape of my neck. The sensations were many and I didn't know which one to enjoy more. And in that moment of delight, I had a feeling of warmth on my puckered hole. Oh my god, that felt so heavenly and taboo at the same time. It was the first time in my life that I had felt a cockhead rub my hole and it is still the feeling that I relish the most. Perhaps he already had precum on his cockhead because it slid forward to my perineum and back to my rosebud.

I didn't need to do anything. I just had to savor my moment of receptive femininity. My arched back could feel the contours of his wide masculine chest. His lips were glued to my neck. His lubricated cockhead was rubbing on my rosebud. And his hands were wandering all over my chest holding me in a loving embrace. I can't describe another moment of equal pleasure that I have ever had in my life. It was probably a long time that we stayed rocked rhythmically in this position. My mind and body had surrendered to his pleasure. My movements were meant to provide him with maximum pleasure. Such was the degree of my surrender to him. Being loved by him just felt right. Nothing else mattered.

While I was enjoying the decadent foreplay, we were startled by some noise in the hallway. I jumped forward in a moment of panic thinking that my roommate was at the door. The noise disappeared quickly but in a swift action I got up and lifted him by hand asking him that we move to the bedroom. As we walked, I led him to the bedroom holding his long sexy cock in my hand. I vividly remember the smirk on his has as he walked behind me.

I crashed face down on the bed and asked him to fuck me. He was surprised by my boldness and said: "I thought you said you were a virgin". I said I was still a virgin and I want to feel him inside me. He needed no invitation. He lifted his t shirt and climbed on top of me. I just loved feeling the weight of his body on me and the sensations of his hairy chest on my back. He got on his knees, his cock sliding in the crack of my ass as he gently stroked every inch of my sexy smooth back. He slid down further rubbing his cock and balls on my thighs as he played with my ass cheeks.

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Ameesh was a master in the art of seduction. He was gentle and slow. While squeezing my ass cheeks, we would very gently graze his finger tips over my puckered hole very so slowly. I would sigh in anticipation and lift my but to feel him more and he would linger his fingers there even longer. I was a plaything for him. As my butt was lifted, more of my cock and balls were available for him to play with. He started stroking my inner thighs and brought the back of his hand to the crease between my thighs and crotch. I was thrilled at the sensation of his hand against the length of my cock. But a feeling of shame dawned on me as well. I wanted to be his woman. I didn't want him to experience my cock.

But as I tried to bring my pelvis down, he lifted me up and palmed by cock and balls in one swift move. I felt so small in his big hands. My copious precum lubricated his palm enough to create a silky sensation as he squeezed my smooth balls. I was splayed open in a vulnerable position being played with by another man. And I was willing and eager for him to do as he pleased. I didn't want that moment to end. His palm was rubbing my balls as he slid his thumb across the perineum all the way to by rosebud. And he didn't stop there. He pressed his thumb firmly on my rosebud but that surprise move made be flinch a little and I shut my anus tightly.

Realizing my hesitation there, he climbed back on top of me and nuzzled his face right next to mine. His thumb was still pressed against my rosebud as he whispered in my ear "Just relax and enjoy the pleasures of our lovemaking". It seemed that was all the reassurance I needed as I relaxed my sphincter and his thumb entered my anal orifice ever so slowly. His dry thumb hurt a little and it was a slight burning sensation I was still getting used to. His thumb went all the way in, and as he gently pulled out. I felt the real joy of being probed. It was as if my love hole didn't want his thumb to recede.

He could sense my unease and asked if I had any lube. I pointed to the drawer on the left side of my study table where I had kept it last night. In anticipation of our romp today, I had made arrangements in advance. That whole shopping errand was an adventure in itself. I had gone to the drug store last evening with a knot in my stomach. My heat was thumping as I walked nervously in the store. Going straight to the condoms section, I looked around surreptitiously first to see if someone was looking in my direction. I sat down on my knees and scanned the section to find what I was looking for. Of course I need to buy a condom. But that was not such a big deal given that I had bought it routinely in the past. My curious yet nervous eyes were looking for KY jelly, the lube that could possibly ease my first time from a painful experience to one of pleasure and liberation. As soon as I spotted a light blue box with the letters KY on it, I picked it up quickly with shaking hands, got up quickly and moved through the aisle with my head down in shame and embarrassment. The checkout counter was an ordeal. I wanted to run away. The line wasn't long but at least it helped me calm my nerves. A young 20-something girl nonchalantly check out my goods, I quickly paid and left. Years later I wonder what went through her mind when she saw me with condoms and KY jelly and a red face.

Ameesh picked up the lube and was back at this position behind me. I felt his left hand spreading my ask cheek as the cold jelly dribbled passed my rosebud. He rubbed his fingers on my puckered hole as he kept pouring the jelly. It was a sensation like no other. The feeling of smooth lube being rubbed onto my rosebud is the singular sensual pleasure that I have reminisced about for many years since then and have enacted it many times with my own fingers. Being the master at seduction, he was slow and deliberate. I was cooing and whimpering in delight as he maintained the pressure of his fingers while rubbing the jelly on my asshole.

At some point, that delight melted away the inhibitions in my mind, and my puckered hole relented to the ministrations of his fingers without any resistance. In fact, I felt his middle finger only when he was already inside by an inch and his first knuckle was stretching my sphincter. My face buried in the pillow, and my ass raised up in the air, I was splayed open in front of him submitting to his well-lubricated middle finger pushing all the way into my virgin hole. The next 5 minutes were a blur as he kept pouring small amounts of jelly onto my asshole while his middle finger kept sliding in and out of my hole.

He would rotate his fingers a little to loosen up my hole for what was to come. The feeling of his knuckles sliding out of my hole was stimulating the pleasure centers deep in my brain. Eventually, he had loosened my hole enough that his forefinger joined the fun and I couldn't stop whimpering. Joined side to side, his fingertips curled downwards as they slid in and out, and I had this desire to pee. I was twisting and turning with lust and desire, and he was fully enjoying the experience of turning me into a feminine fuck-toy.

In one abrupt motion, he pulled out his fingers and wiped them clean with the tissue lying next to the bed. I suddenly felt empty, wanting for more. I lifted my head and begged him, "fuck me, please". I picked up the condoms that he put on the side table, turned around on my knees to face his cock as he was standing on his knees on the bed. I couldn't hold myself and planted a kiss on his cockhead. He pushed himself gently on my inviting lips and I couldn't help myself opening my mouth and taking is thick knob dripping with a string of precum. He jerked in excitement as he felt the warmth of my mouth on his cockhead.

It felt so right performing the ultimate submissive act. I sucked on his cockhead like a lollypop, holding his cock in one hand while supporting myself with my elbows. I would take it out, roll my tongue over it and take it back in one swift motion. It was his turn to give out a manly groan as he was relishing the pleasures of being sucked by a willing homosexual lover submitting to his masculine power. His hands were holding my head guiding his cock to greater depths of my open mouth.

I pulled out his cock, looked up in his eyes and begged him to fuck me. I tore open the condom sachet, pulled out the condom, rolled it on his cock and was back to my original position on my stomach. It was happening fast. Neither of us could control our urges anymore. With my legs joined together and ass slightly up in air, he positioned his legs on both the sides of my body as he lowered his body to conform the contours of my naked form.

As his large frame engulfed my nakedness, the feeling of being lightly crushed under his weight made me feel so secure. I felt that I was needed by someone. I wanted to give myself away to this masculine man as his muscular hairy chest rubbed against my smooth back. He had supported himself on his hands as his scruffy face cuddled against my shaved cheeks. I leaned my face into his, our lips only millimeters away as both of us felt each other's heavy breaths. His raging manhood was pressing on my ass as I pushed my ass up in the air to feel him more. It was a dance of a bigger python entwining and engulfing his prey before going for the kill. The only difference that it was a consensual moment of erotic pleasure that the prey wanted more than the predator.

I gasped as he impaled his big manhood into my lubed-up entrance in one swift thrust. All that preparation and foreplay was not enough to handle his bulbous knob into my virgin hole. I shrieked in pain as he held me tight and in place. I was woken up from my sensual slumber by the onslaught of his ravaging member into my tiny slippery orifice. He lowered his full body weight in order to contain me as he assured me in whispering tone that this will go away soon if I open my hole willingly and we wait in this position without any further thrusting. He brought his face back to my cheeks leaving a trail of kisses from my ears all the way to the corner of my life. I opened my hole as the sensuality of that romantic moment flooded my mind. I felt heaviness in my heart and a knot in my stomach as I turned my face toward his. With closed eyes, I waited in anticipation to feel his lips on my mine. It was the ultimate feminine act for a grown man with a hard cock between his legs. Surrendering my lips to his eased the heaviness in my heart as I was feeling light in my stomach and a slight pain my heart. My soul had given away its individuality as it was willing to be entwined with my plunderer in this moment or romantic delight.

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