Reacquainting Oneself Ch. 05

The guys washed up after their afternoon outdoors, making themselves presentable. They wasted little time getting dressed, knowing they could never compete with their ladies. However, as I was learning, guys can look good with the simplest of clothes. Their muscular chests and arms could be traced under a simple t-shirt, and a pair of shorts showed off their legs.

When I saw Robert, I had to resist following him into the bedroom and pouncing on him immediately. The sweat gleaming on his body, and with the confident stride as he walked into the house. It was almost more than I could bare.

The look that Robert gave me upon his return made my heart leap. The lustful glance gave me that extra boost of confidence. This was my guy, and I was his girl.

We settled into a relaxing BBQ. The ladies had a head start on the drinking, but the guys were quickly catching up.

Relaxing on the deck, I decided to sit on Robert's lap. My forwardness surprised him. Not that I could blame him. 24 hours earlier, I would not have dared to do such a thing. Now, comfortable in his embrace, I leaned in to kiss him.

He rested his hand on my thigh, which was exposed by the short dress. I kissed him more passionately, opening up for a French kiss.

Seated as I was, I felt Robert's erection press against my ass. I wiggled a bit to excite him further. It pressed further between my ass cheeks, enticing us both.

Our brazen foreplay was not remarked upon by the others. Their own behaviour was equally sultry. So, although we maintained a relaxed evening of chatting and drinking, there remained a constant undertone of eroticism. Roving hands slipped under skirts. 'Wardrobe malfunctions' pulled breasts out from their loose-fitting dresses, and were suckled. Gentle hands slipped under the waistband of the guys' shorts, and stroked the hard cocks poorly hidden below.

Gone was my fear and shyness of the night before. Tonight, I was a vixen who knew exactly what she wanted, and I was letting my man know it in no uncertain terms.

We all went to bed early that evening, though it was quite clear that sleep was the farthest thing from anybody's mind.

I decided to keep my heels on. With the practice and guidance I had received that afternoon, I wanted the sway of my hips as Robert and I walked upstairs.

I practically pulled Robert into the bedroom, and pushed him onto the bed.

I slipped out of my dress, allowing it to fall to the floor. I strode towards him, giving him a show with my sexy lingerie.

His lustful gaze was all I needed, urging me to go further.

I knelt before him, and reached for his shorts. With his eyes upon me, I unzipped his pants, releasing his already hard dick. I licked my lips, and proceeded to pull down his shorts and briefs together. With free access to the object of my desire, I parted his legs, and shifted forward to be between those muscular thighs.

I wasted no time, immediately engulfing his cock. The groan from Robert, and the twitch of his cock, told me he had been anxious as well. I licked and bobbed, coating his cock with my warm saliva.

Knowing I could deep throat him, I was eager to do it again. I systematically bobbed and adjusted my position to take him in deeper. My tongue lapped at the underside of his cock, causing him to jerk.

Robert had a firm grip of my hair, pinning me to his cock, not that I was going anywhere.

My breathing was becoming more laboured, and I felt light headed. It gave me a sense of euphoria. I intensified my efforts.

And then success. My lips touched the base of his cock. His cock was buried down my throat. I fought to keep his member deep within me as my lungs burned from the lack of oxygen.

Eventually I pulled back, gasping for breath. He allowed me a moment before inserting his cock into my mouth. Yet, he maintained a firm grip on my hair, preventing me from going down on him.

I didn't know how to react at first. His cock slowly pushed into my mouth, and then out until just the head was between my lips. He repeated the movement more forcefully. I could only adjust my mouth and throat to accept his cock. All movement, and all control was with him. It struck me how humiliating this was, but exciting at the same time. My mouth was just a hole being fucked.

He thrust in harder and faster. His grip on my head tightened. I was gagging on his cock, but he paid no heed to my discomfort.

I tasted the first droplets of precum, and sensed he was getting ready to climax. I held onto his hips, bracing myself. He buried his cock deep in my throat, almost all the way in, and he stiffened.

The groan shook me first. Then the ropes of semen filled my throat. I attempted to swallow it all. My first taste of semen.

Periodically I had tasted my own cum after masturbating, but this was so much more. More volume. Yet, more importantly it was another man's seed. I had serviced another man, and allowed him to use my mouth. I was filled with the salty cream. Actually overfilled, as it dribbled down my cheek. I scooped it up with my finger, and licked up the cum that I was not able to swallow initially. A huge grin on my face.

Robert looked down at me, observing my reaction to the taste of his cum. He sat back, relaxed, and fully sated. He shifted back on the bed, resting against the headboard.

Following his lead, I climbed into the bed, and cuddled up in his arms. "Thank you," I said softly.

He found this quite amusing, me thanking him for the privilege of sucking his cock. He stroked my head, and maintained the theme, "You're welcome."

For a moment I was worried that I had acted impulsively by sucking his cock, and allowing him to climax. Although, it didn't seem like I had much choice, particularly as he fucked my mouth. Yet, I still felt the ache to have him inside of me. I longed for that monster cock to stretch my ass, and overpower me with pain and pleasure.

Robert must have sensed my thoughts, or perhaps it was his own fantasy speaking. His hand slipped between my ass cheeks and rubbed against my puckered opening. "You better be ready for another pounding sweetie because I have been thinking about this ass all day."

I kissed him. "I'm ready when you are. Always."

He kissed me in return, his tongue pushing into my open mouth. Leaning my head back to fully accept his kiss, to surrender to him.

"You truly are a natural cocksucker. I have hardly ever cum from getting a blowjob."

I beamed with delight, proud to be a cocksucker.

"I just need some recovery time," he continued. "And then I'm going to fuck you so hard you'll have trouble walking tomorrow."

I giggled, and kissed him again.

Laying next to him, stroking his muscular chest and arms, and staring into those piercing eyes, my mind wandered to all the questions that had developed. He clearly was intent on this. His comforting embrace, and his fingers now slowly piercing my sphincter, told me this was his erotic fantasy being acted out as much as mine.

My hand brushed his cheek, and then I kissed him. A deep and passionate kiss. Then holding his gaze to see that wonderment, and that gentle lust. "Robert, this weekend was no accident was it? I mean, you had this whole thing planned didn't you."

For a moment he hesitated. He had obviously set me up. Was there any point in lying? Everyone here this weekend expected me to be feminized, and to sleep with Robert. The only question was whether I would acquiesce. I knew Robert would never force himself upon me. "Yeah. When I heard you were in the city, it brought back so many old thoughts. I had to give it a shot."

I suppose I should have been upset. He had planned this weekend. There was never going to be a casual friendship between us. I was never going to be the confident guy who could socialize with women. This was always going to be my place, in lingerie, yearning to be the one being fucked. The high school buddy pretense which brought me here was a lie. Rationally, I should have been pissed off.

But I wasn't. I pondered all this for a moment. I truly wasn't. A lifetime of expectations of what I thought I should want blown away, but I didn't care. It felt good to be desirable. It felt good to be sexy. It felt good to taste his cum as its flavour still lingered on my tongue. And yes, his fingers were but a welcome preamble for the fucking to come.

I kissed him, telling him without a word that everything was ok, and that I was happy to be here. It did prompt some lingering questions though. "Robert, did you fantasize about me in high school? I mean, like this?" I nodded towards my body, and the erotic lingerie I was wearing.

He breathed out, and paused to find the right words. He nodded. "Yes. Well in retrospect, yes." He stared into my eyes, entrancing me. "I didn't know what I wanted back then. And of course, you have all the peer pressure. And I had all the girls wanting to be with me, which is what every teenage guy is supposed to want. Let's face it, I had the movie-like teenage years. I was on the championship football team. I was never top of the class academically, but I was never the dumb jock either."

I nodded, remembering full well how he had been Mr. Popular.

"And I always liked you in school, but I could never put my finger on why. I figured it was just sympathy. You were constantly being picked on."

Understatement of the year. However, it was now oddly comforting that he saw it.

"And then there was that time in the locker room. You were really hot. I was attracted to you more so than any of the girls at school. There was a certain vulnerability. Perhaps an androgynous quality. I don't know. I certainly didn't know then. All I know is, there was that raw attraction of, oh... she's hot!"

It startled me to hear this. The moment of my greatest terror was the moment which had inspired him to see this other me.

"But then you took off. Terrified. And in the coming days, you bristled at the slightest mention of it. Which of course everyone did. How could I tell you what I thought? You would have thought I was taunting you. And there was probably a bit of cowardice as well. If I had expressed any of these feelings, the guys I called my friends could have mocked me as a faggot, or a homo, and lord knows what else."

Given that I had been called all those things, I understood all too well. Perhaps it would have been comforting to hear a kind word, but would it have made a difference? Would my self loathing have improved if their harsh words had an element of truth, and Robert had comforted me?

"So, you wanted me back then?" I meant that in the truest sense. Had he wanted me in the same way as he had me now, in his bed?

He nodded. "It wasn't until years later that I understood that though. I had a friend in university who surprised me one evening in the dorm room by getting on his knees and sucking me off. For me, it came out of nowhere. Although, I gathered later he had been building up the courage to do it for months. But still, it didn't feel quite right. I was never attracted to him. Mind you, that didn't stop me from accepting some more amazing blowjobs." He grinned.

I shared in the laugh. As the alpha male, why wouldn't he accept servicing?

"After university I started to experiment a little. My porn watching veered towards sissies and transsexuals. It was probably around then that I thought back to you wearing a dress, and fantasizing about being with you."

I blushed. His touch, his fingers inside me, driving me crazy. This was far more than a weekend dalliance or experimentation.

"And while I never had a problem connecting with the ladies, they were never as good at giving blowjobs as my university friend. If they would even do it. And none of them gave up their ass. It just lacked something. Intrigue maybe. Also missing was the subtle dominance. With my university mate, I could simply point to the floor in front of me, and he would instantly drop to his knees and suck me off."

I smiled. Yes, there was a subtle dominance and submission. I regarded him with a form of superiority, as a real man. He was not the only one who had been watching sissy porn. I dared not put it into words, but he could see it in my eyes that I understood.

"This led me to the gay bars. I didn't know about shemale or pansexual clubs. I just figured I was gay or bi. Yet, the moment I stepped inside I felt like a fish out of water. I put it down to nerves, and suppressed homophobia. But it was more than that. I was not attracted to guys. The only time I perked up was when I saw some drag queens." He laughed, clearly remembering the moments as he spoke.

"I started to frequent alternative dating sites, seeking out trannies and crossdressers. And I was definitely feeling I was on to something. But I never really found anyone. I hooked up with some trans prostitutes. And that was fun. The crossdressers were either a nervous wreck that would bail at the last minute, or they were gay guys who wanted to be fucked."

His tone switched from serious to joking. "Mind you, that was fun sometimes."

"And remember, I'm still a recent graduate. I was mainly working my ass off, struggling to pay the bills, and building my career. I didn't have a lot of time to indulge, and I certainly didn't want my colleagues to know about my unusual proclivities."

"Wow," I muttered. I didn't know what else to say. It was amazing that he had explored so much, that he had such confidence. He had done all this while I hid alone in my apartment, only daring to dress as a woman on rare occasions.

"I wish I hadn't run." My first coherent words. "In high school I shouldn't have run. I should have stopped, did a pirouette, air kissed to my admirers." I laughed. "I don't know. I just wish I could have accepted my femininity. Years of running, and the greatest guy imaginable was right there all along."

I kissed him passionately. I could cry over lost moments, lost years, but right then I wasn't feeling sad. I was feeling something more primal.

I stroked Robert's cock, and found him once again hardening. I kissed him as my hand continued to stimulate his cock back to life. His fingers now pierced my ass with force.

He reached into the side drawer, and retrieved a condom and some lube. I watched transfixed as he placed the condom over the monster head.

"Allow me," I whispered. Then I placed my hand over his cock, rolling the condom down. It was funny that this was my first time putting on a condom. I'd never had occasion to wear one, and never would.

I watched as he squirted lubricant onto his fingers, and then once again reached behind me. My hole tightened instinctively as the cold gel pressed against it. That only lasted a moment as it warmed up, and his fingers slid in easily.

My excitement was building. I kissed him again, letting him know in no uncertain terms that I wanted him inside me. I pushed down my panties, sliding them down and off. I wanted nothing to restrict access, flimsy as it may be.

I applied lubricant to his cock. The gel gliding along his now rock hard shaft. We were both more than ready.

I straddled him, surprising him once again with my initiative. Momentarily, I was embarrassed by my little penis pressing against him. Yet, then I thought that small penis was one of the reasons I was a bottom, a sissy, and now about to take his gorgeous cock into my ass.

Robert lay back, allowing me to set the tempo for my penetration. Holding his cock at my sphincter, I slowly lowered myself onto him. There was that initial pain I remembered, but I managed to push past it. The lubricant certainly helped. I was able to take half of his shaft into me before I had to pause.

His cock remained inside me as I adjusted to my insides being fully stretched. The pain becoming an ache which felt nice.

"Ok sweetie, sit back. It's time to take me all in." He gently prodded me.

I nodded. While I may have been on top, there was no question who was in control. No matter the pain I may have felt, there was no question of me disobeying. I needed to take him deeper. I sat back slowly, stretching out my ass as his cock slid into me.

I groaned out in response. Fighting the instinct to stop. Accepting the pain, as I knew the pleasure would come. And it did, as his cock rubbed against my prostate. My groans of pain devolving to moans of pleasure. His whole cock within me could only be described as filling. The dull ache of my stretched anal muscles, the slippery gel squishing within my ass, and that rigid shaft riveting me in place.

A moment of adjustment before I began rhythmically rising and falling. His cock stretching me out and pushing against my prostate with each thrust. I made sure to rotate my hips to add stimulation to his cock, and rub it along my insides.

I was now squealing with delight.

And I wasn't the only one making noise. Sure, Robert was grunting with each downward thrust I made, but I was referring to noises from another room.

Mitra was voicing her own pleasure from being fucked. It was amusing that I could already recognize her distinctive high-pitched moan.

I slowed my pace to be fucked in unison with her squeals. Her pleasure inspiring my own.

Robert could see what I was doing, and he chuckled. My tight ass muscles gripped his cock, and stimulated him with each thrust.

I learned down, laying on his chest, and taking care to keep his cock inside of me. I kissed him. Then with a wicked grin, I was reminded of a certain challenge made in jest that morning.

I kissed him again, staring into his eyes. "I want you to make me scream like her."

Robert sensed there was a story behind this, but he said nothing. He grinned and nodded. Whatever the reason, this would be fun.

He surprised me again with his strength, lifting me off him, and rolling over. In a flash, he had me where he wanted; on my knees, legs spread, and face down. He was behind me.

Let's be honest. It was where I wanted to be as well.

Initially, I buried my head in the pillow. Yet, he pulled it away, and tossed it to the floor. "Now, now baby. You wanted to scream."

He was right. Although my nerves were heightened to a fever pitch.

I didn't have long to wait. He gripped my hip with one hand, and guided his cock to my hole. And with one hard thrust he was inside of me.

I screamed out with pain and ecstasy. Goal achieved.

His passion had taken over, and he had no interest in being gentle. He fucked me fast and hard.

I was loving it. The tightness. His monster cock pounding against my sissy g-spot. And then there was the general sense of being enveloped by this man, overpowering me from behind. A mere 48 hours earlier, I could never have imagined how pleasurable this could be. Now, I wondered how I ever lived without it.

I voiced my pleasure. I was moaning and crying out with every thrust. Calling out for more.

"Oh yes! Fuck me! Oh yes! Ohhh, don't stop!" One long litany of cries and moans with no meaning other than to beg him to keep fucking me hard.

Gone was the timid boy who was desperate and terrified of sex. There was now only the sissy slut who knew she was happiest with a cock deep in her ass.

Robert was certainly not disappointing. He was fucking me with abandon. The earlier climax from the blowjob was giving him staying power.

I was a quivering mess beneath him. My legs shaking, my ass stretched, and a dull throb which felt amazing. My mind was utterly blank, awash with sensations.

I sensed him tightening up. He buried his cock deep within me. His hands gripped my hips tightly. His thrusts were short and fast.

The sensation pushed me over the edge, and I squirted onto the bed before me. I came without my penis ever being touched.

Robert was not far behind. He let loose a fearsome growl as he buried his load deep within me.