A Night with Jim

by Somewhat Straight

17 Apr 2014 6759 readers Score 9.3 (147 votes) PDF Mobi ePub Txt


My friend of many years, Jim, had just given me the most mind shattering blow job of my life. I had never before been with another guy even though I had fantasized about it for much of my life. The wait had been worth it. Having sex with Jim had given me a perspective I'd never before had being with a woman. That's because I wanted to be the woman.

In the afterglow of our 69 experience, we were both licking each other clean. I found myself tenderly kissing his semi-flaccid penis acknowledging how much I had wanted this to happen. I still saw myself as a man, but having been so intimate with Jim I found myself wanting to be his woman. I knew I would try anything he wanted, anywhere he wanted to do it. I prayed he would soon take me as a man takes a woman. I wanted to be filled up by him and feel his manhood owning me from the inside out. I wanted to gaze into his eyes as we gave ourselves up to our wicked desires.

As if he could read my mind, Jim lubed up his index finger and started to insert it up my ass. I was embarrassed that I squealed like a girl but he could tell how much I wanted it. He spit on his fingers and managed to insert two this time. I got on all fours in front of him so he could reach over and prepare me while I worked on making him hard again. It was so intimate suckling on his manhood while anxiously waiting for him to take my virginity and claim me as his own. I knew it would hurt, but I looked forward to learning how to please him in every way. I wanted to learn everything there was to know about how a woman can best please her man. In this one night I had discovered how much I love cock and that I desire to please the man I'm with as much as any woman can.

I couldn't believe that this gorgeous man would get aroused being with me. But there he was, getting hard already and I marveled as his penis grew in my hand and mouth. My sexy bull started to take me doggie style, but I stopped him. I turned on my back facing upward and shifted my ass so we could make love in the missionary position. I pulled him down to me with my legs wrapped around his lower back and my hands moving down to his butt cheeks. I knew I had become his sexy bitch as I caressed his ass. I was delighted when his muscles tensed and rippled in response to my lightest touch. I felt his cock harden even more as it rubbed up against my own. He started to thrust his pelvis back and forth across my stomach while we enjoyed the feeling of our cocks sliding up against each other. I may have started this gay encounter, but Jim was in control now.

He shifted lower and dragged his fingers across the pooled precum on my stomach. Then he gently slipped them in and out of my anus. I was so ready for him to take me. He whispered in my ear, "I'll be as gentle as I can, but I need to be inside of you. I've never wanted to be with anyone as much as I want you right now. Our lives are about the change forever you sexy bitch!"

The next thing I felt was the hot tip of his throbbing rod pressing against what was about to become my vagina. With his right hand, He gently coaxed and positioned his cock to enter me as I tried to relax my sphincter muscles to help him in. He tenderly kissed my lips and soon his tongue was caressing mine. I was so overwhelmed with passion that my muscles relaxed completely. In that moment, as I gave my virginity to Jim, I knew that nothing satisfied me better than being fucked by this man. I whispered, "Take me all the way with your beautiful cock. You complete me like this. Fill me with everything you have. I want every bit of you inside of me."

With each gentle stroke this sexy man was able to slide more of himself into me. I kept adding more saliva with my hands as he slowly withdrew and that helped him go a little deeper with each gentle but undeniable penetration. I hardly noticed the pain as I was far too caught up in the moment and how sexy I felt. At last, he slid into me balls deep and held me tight as our tongues intertwined. Then he started to slowly move back and forth giving me the full length of his gorgeous cock with each stroke. I was rock hard and my stallion was about to ride me for all I was worth.

I felt my transition was now complete. I loved my new role as the deliciously feminine Delilah seducing her Samson. I had started this evening hoping to convince Jim to spend the night with me. I had no idea this moment would stand alone in my memories. As his manhood slid into me, I willingly became his bitch. I no longer had to hide who I was. I knew this gentle, gorgeous stud would not hurt me. I shuddered in his arms in anticipation of what was to come. When I opened my eyes, he was looking at me with an exciting combination of longing and lust. Any hesitation on my part was gone. I was his.

We continued to French kiss as his speed increased. I couldn't believe what a turn-on this was with his cock massaging my prostate gland deep inside. I began to realize that I could cum while he fucked me with no other stimulation. I was so excited I groaned "I don't fucking believe it. You're such a fucking stud you're going to make me cum like this!"

The kissing stopped as Jim started slamming me for all he was worth. He was hard as glass and he strained to say in a raspy yell that he wanted to cum with me. I was becoming even more aroused every time his balls slapped against my ass. I had brought out Jim's animal lust and I could feel his power drilling into me with every stroke. He was like a frenzied pile driver that couldn't be satisfied.

The moment of truth had arrived for both of us. Jim frantically squeezed my butt cheeks as he poured his cum into me with loud, shuddering gasps and masterful strokes. I could actually feel his cock pumping his essence inside me as my own orgasm erupted.

I came like I had never experienced before. This new orgasmic sensation started deep within with Jim's cock rubbing furiously against my prostate gland. I was so into my new sexual role that my brain willed me to cum like a woman. The ecstasy flooded over me like never-ending waves. I could feel my cum flooding across my stomach and spilling off my hips as it spewed forth. I could feel Jim's cum making its way out of me as he continued to stroke me into submission. I pictured what we must look like to someone watching us from across the room. All I could feel was a sense of fulfillment, pride and passion over the intense pleasure we had just shared. To anyone else we were two men lying together in the afterglow of a mind-blowing sexual encounter. But Jim was clearly all man...my man, and I was his lady.

I held onto Jim's gorgeous cock savoring the feeling of him filling me up from behind. We continued to kiss tenderly as we both acknowledged our new sexual preference. I was already thinking I would be ready to go again in just a few minutes. But for the moment, I had him locked firmly inside me as we kissed and I playfully caressed his ass and balls.