The Ballad of Bill and Jamie

I could feel his hand gently squeezing my ass through the fabric of my jeans and the stretch lace panties Bill likes so much to see my tender tail wrapped in. It was a sensation that I dearly loved. I twisted my hips just enough to let him know I felt him, and that I approved. I loved the way Bill touched me, and I loved the way our relationship had evolved.

I was just 22 when Bill's wife died, he was 41. She died in a car accident, and he was devastated. Living just three houses down from my apartment building, I watched him devolve into a wreck himself. I had secretly found him exceptionally attractive. He was a good man, kind, gentle, and very funny. We enjoyed a lot of the same books and movies, and he often regaled me with stories of his days in the Marines. I would eagerly ask questions, and laugh in as subtle flirty a way as I could anytime he told a joke. My only wish is that we could have begun on a more consciously consenting way, but looking back on it, we began the only way we could have.

I had gone to see him one afternoon, and found him blindly drunk, sitting on the couch. He wasn't making much sense, mumbling about being lonely, missing the way his wife 'pleased' him.

"She was a fine woman." I said, as I helped him up and steered him to his bedroom. I had done this several times in the past year or so, and he never remembered that I had even been there.

"She was a lazy cow!" he slurred out as we entered his bedroom. He fell onto the bed, and was almost comatose right off. I pulled the blinds in the room, and it left the room with very little light. I had put him to bed a few times before, but this time I took the initiative to free him of his clothes, hoping to catch a glimpse of the real man. His shirt came off easily, though he helped very little. He wasn't wearing shoes, so I grabbed his socks by the toes and a gentle tug slid them off. His pants slid off with equal ease, and the head of his cock was peeking at me from the gap in his boxers. I stood there, transfixed by the sight of his slumbering member in the near dark, God it must be really long for that much of it to be showing through his shorts.

I turned to lay his pants on the chair in the room, and he sleepily groaned out, "Come on Jean, let's spoon a little."

"Sorry Bill, it's me, Jamie."

"Jeanie, stop fucking around and get in here."

I sat down on the edge of the bed. "Bill, sleep it off, I'll come back later."

"Please Jeanie, I've missed you so much, for old time's sake. Just this once."

"Just once what?" my heart was pounding, and it was getting really hot in here.

"Just lay down." He was pulling at my waist.

I lay down next to him, and he snuggled up next to me, and looped his arm around me, his hand snaking its way under my shirt and deftly finding a breast, immediately began stimulating its nipple. I breathed out hard as the feeling of him fingering my tit flowed through me.

"You like that?" he mumbled.

"Uh huh!" more breath than words. Could this really be happening, I had fantasized about this so many times. I had never found another man attractive, but Bill was handsome, funny, and when I was around him, I felt like a giggly little school girl.

He pushed his semi-hard penis against me, "That?"

"Uh huh!" breathing harder.

He began pulling at my jeans, "Wait, I've gotta pee."

"Hurry back baby."

I almost ran to the bathroom, heart pounding, I was scared, and was steaming with lust. Do I dare go back in there? What would he do when he realized I wasn't his late wife? Was there a chance he would have sex with me and not remember it? I turned off the bathroom light and standing there in the dark, I decided to chance it. I slipped out of my shoes and socks, pulled off my shirt, and jeans, and stuffed my underwear in the pocket of my jeans. I gathered them all up and opened the bathroom door. Bill was slumbering deeply it seemed, as I padded my way to the bedroom door, and left my clothes in a pile (just in case I had to make a hasty retreat).

I stood at the edge of the bed for what seemed like an eternity. His breathing was long and slow as I lay down next to him, and nestled in close. His reaction was immediate. He turned to his side and his arm came around me once again.

"That's more like it." He said dreamily, and began kissing my shoulder gently. It felt WONDERFUL. I arched my back and it had the effect of pressing my virgin tail into his pelvis. His penis was fully erect, and it slipped neatly into the crevice between my legs. It was strong and hard, and with a mind of its own was seeking the warmth of yielding flesh.

I coated my fingers with my saliva and reached down between my legs. I felt him there, hard, and longing to use the flesh that lay in his bed. His penis was long and sleek. It felt perfectly intoxicating as I spread my slobber over its bulbous head. I couldn't help lingering over it with my trembling fingers, it felt so good, this was more right than anything I had ever felt. His hand left my breast and found my hip, and he drew back his shaft. I drew up my knees, and tilted my pelvis back searching for the throbbing heat that was positioning itself to expend its need inside me as he pawed his boxers down, unleashing his pent up need on my virgin ass. I found him hard and relentless as he rocked forward intent on claiming his dream. His head entered me and I sucked in as much air as I could get.

"Aahh, you're so fuckin' tight!" he slurred, as he ventured into my unexplored back country.

"Aaahhhhh." I cooed submissively, aching through the agonizing pleasure of being butt fucked for the first time. I felt as though he was going to rip me in half, though I could do nothing but squeal in pleasure, as my body yearned for more. The pain was intense, but it very quickly turned into a heavenly pleasure, as his ravishing prick pressed the urgency of its need deep into me. My flesh heard his tale, and heard it very well. My body accepted his explanation of how the universe should turn, and begged to be allowed to take its rightful place as his.

"You still like my cock?" his full length was inside me and all I could do was lay there and be repeatedly skewered. The pounding he was giving me was quite thorough, and I understood there in the dark, that I had not experienced anything more needed.

"Yes! God yes, Baby! Fuck me good!" These words fell from my gasping maw as if they had been waiting an eternity for this moment.

All I could do was gasp as Bill pushed his hard stick deep into my hole over and over. After what seemed like a thousand years of being stroked, his pace quickened for brief moment and he unloaded as deep inside me as his length would allow. That was it! He kissed me gently on my back as his slimy cock slipped silently out of my quivering man pussy, then rolled over and fell into a deep sound sleep. The first time we had sex took less than five minutes, it had taken me longer to screw up the courage in the bathroom to disrobe than it took for Bill, and his not so little friend, to convince me that I belonged right there in his bed. I got dressed slowly there in the bedroom, thinking that I could have lived from that moment on with his erection using me for its filthy pleasure. I walked down the hall, out the back door, and down the street to my apartment building in a sexually induced haze. With every step I could feel his thick creamy cock sauce oozing out of my aching hole. His liquid made my crack slippery, and the sensation of my flesh sliding against itself was maddening.

I ate dinner alone, retired to my room, and laid awake all night thinking about having sex with Bill. Would he remember? The feeling of the hair around his cock being mashed against me as he thrusted inside me. Did he know it was me? The way he held my hips. How amazing it felt and how shocked I was that he could get all of his length inside of me so easily. Would it happen again? The sight of his penis peeking at me through his boxers. If he only had a vague recollection of having sex, would he freak out if he figured out it was me? What did getting off do for him, and could he enjoy sex if he consciously knew it was with a guy? If being with a guy felt that good, was I truly male? Had it really been good for him? Would he want more?

I fingered the hole he had used and it came to life immediately, aching, and longing for more attention. That settled it, I wanted more. I truly wanted more with Bill, but if it never happened with him again, I wanted to explore this as part of my life. I understood that most young men didn't long for this, but I couldn't help it. Being with a man was incredibly more satisfying than any encounter I had ever had with any female. It was WAY more pleasurable to play with my own titts, than to play with a girls'. And pussy was nice and all, but cuming for me was always VERY anticlimactic. The brief encounter with Bill had confirmed it for me, it was infinitely more pleasurable for me to be fucked in the ass for a few minutes than anything I'd ever experienced using my dick, including cumming.

To be continued......