Bac Bay Bottom

Background

In May 1994, I was traveling for business to Boston, a city I knew well from my college days. I stayed at the Marriott at Copley Place and had, because of a scheduling change, part of a day to kill before going on to Cleveland.

While I usually dated women back then, I had a couple gay experiences earlier in life. As I thought about how to spend the down time in Boston, the idea of using it for some sexual exploration appealed to me.

This story is inspired, as they sometimes say at the movies, by real events. Some of it actually happened, other parts are embellished or what I wish had happened. The location and circumstances are unchanged.

I was fresh out of the shower, a hotel robe loosely pulled around me, as I sat down on the edge of the bed. I could hardly believe my morning thus far. I had gone online and entered a Boston M4M chat room and began a conversation with a guy, Henry, who was virtually across the street. I had ended up in his office, first dropping to my knees to suck his large, black, cut cock, then against the wall as he fucked me from behind. I asked him to stay inside me after he had cum, and it only took a few strokes for me to reach my own climax.

On the way back to my room, I encountered a guy in the elevator who bluntly propositioned me and assured me that he had "a big dick." This caught me by surprise and I wondered if my forehead had "I'm a horny bottom" stamped on it. But, still aroused from the office fuck, I got off the elevator with him and walked to his room. There I discovered he had a partner, who was the one who was really hung. As they were both primarily tops, they wanted to take me spit roast style, with the large cocked partner filling my ass and the other using my mouth. While I didn't exactly cum, it still was an intense and extremely erotic experience.

Now, back in the room, cleansed of the sweat and remnants of multiple sexual encounters, I was assessing how I felt. Although a little sore, my ass - or was it now my cunt? - still tingled with the memory of being fucked by two well-hung cocksmen. God, it had felt good, in a slutty sort of way, to be filled and used like that. I definitely was best suited to being a bottom. And now my body felt empty and not entirely satisfied. I chided myself for wanting more.

The thing is, I

did

want more. I wanted to cum again, with a big hard cock inside me. I looked around for the bedside clock - there were still a few hours before I needed to check out and head for the airport. I considered my options. I could see if the guys a few floors below wanted a second round, but I had the impression they had plans for their day. Oddly, too, while the fucking they gave me had been exciting, I sensed that I wanted - my libido needed - something more intimate and sensual.

That led me back to thinking about Henry and his incredible cock. Yes, I know many erotic stories and porn videos showcase a long, thick black cock, but this one was real. Honestly, it was beautiful, and I am sure that was the first time I ever thought a man's genitals were attractive. From the cut head with wonderfully flared glans, to a thick base and a set of heavy balls, it begged to be worshipped with a wet mouth and caressing hands. And then there was the way it felt inside me; it made me want to have a pussy to please him.

Henry had expressed regret that I was leaving town, and his hug as we parted was more than perfunctory. I wondered what he would be like in the more comfortable circumstances of a private hotel room, with a big bed, and the first lustful session behind us. Would there be foreplay? Would he try to kiss me, and if so, how would I react? Would he go beyond fucking, and make love to me?

Huh?

What was I thinking? What was happening here? By this point in my life I'd bedded several dozen women; how was it I suddenly was wondering how a man was going to treat me during sex? Had the morning experiences really feminized me that much? As I sat there, turning my feelings over in my head, the answers were unclear, but my desire to be filled by - and to give pleasure to - a man's hard cock was undeniable. And while I could, I was going to do something about it.

Henry's number was still written on the pad by the telephone. I picked up the handset and dialed the number, not so much with trepidation, but with concern about how much I wanted this. What if he didn't?

The call was quickly answered at his end, and Henry's distinctive voice - a black bass tinged with a Boston accent - answered. I'm sure my first words sounded stilted: "Hello Henry. It is James. From this morning."

His response was immediate and reassuring: "Oh, James, I am so glad you called. I was wondering how you were. Are you ok? Our time together was short, but I felt like we connected. In fact, I was sitting here thinking about you. Please tell me you are going to stay longer in Boston - I'd like to see you again."

I was, at once, both pleased and a bit annoyed with myself. His voice sounded sincere, even caring. How was I going to tell him that I wasn't staying longer, but I wanted him to fuck me again?

"No, Henry, I still need to leave for Cleveland this afternoon, but that is a few hours away. I'm sitting here in my hotel room and thinking about what we did this morning, and how good it felt, and - at the risk of sounding like I am just using you for your amazing cock - I was wondering if you'd like to come over and spend a little more time together."

An amused laugh greeted my last line, followed by the words I hoped to hear: "What's your room number? I'll be over in a few minutes."

I gave him the room number and mentioned something about the driest route to the hotel to avoid the ongoing drizzle. Henry expressed his appreciation for the suggestion and then rang off.

Oh, my. It was going to happen.

I straightened the room, and the bed, and even brushed my teeth. I decided to stay in the robe; if all went well, I was going to be naked soon anyway. At least I hoped.

While I was expecting it, I was startled when I heard a knock on the door. I checked the peephole to confirm it was Henry, and then opened it. He smiled as he saw me, and I stepped back and invited him to come in. As I closed the door, he walked towards the window end of the room, then turned and said, "Even on a rainy day your room has a nice view, but the one in here is better."

Henry's compliment put me at ease and I walked over to him and we embraced. This hug lasted longer than the last one in his office, and his hands ran down my back and cupped my ass through the terrycloth. He pulled my crotch into his, and squeezed my cheeks, making me feel wanted and desired. Then he leaned back and teased me about the robe.

"In a hurry to get started?"

I mumbled something about taking a shower, but he seemed more interested in gently guiding me over to the floor-to-ceiling glass that was the outside wall of the room. He turned me so we were back to front - how we had fucked in his office - staring into the gray, rainy day and the cityscape around the hotel. His arms reached around me and his hands opened the top of the robe and found my stiffening nipples. His fingers squeezed them, hard, eliciting a moan from me. Meanwhile, his mouth found my uncovered neck, and he nuzzled me. I could feel his erection through his pants and my robe, as he ground a bit into my ass.

It was a wonderfully sensuous moment, and it somehow perfectly fit how I hoped we would come together. As his hands moved from my nipples and began exploring my skin, the robe parted. Henry took the opening to reach down and cup my balls and cock, although the finger strokes he applied to the latter made it feel more like a big clit. His touch was great and I was becoming incredibly aroused.

The embrace lasted for another minute or so, until I stepped forward, turned and shrugged off the robe. I appreciated the way he looked at my naked body, even if it wasn't the perfect gym form; there was real desire in his eyes. I knelt down in front of him - again, like I had in his office - and reached for his belt buckle and zipper. I had both open in a few seconds, and after pulling his pants and underwear down, his hardening cock popped up.

I gotta say it again - it was a beautiful fucking cock. I was immediately drawn to it, first to caress it with my hands, then worship it with my mouth. I heard Henry moan his approval, but was mostly lost in my own world, giving him pleasure as he pulled off his jacket and shirt, and then stepped out of his shoes and pants. Through it all, my mouth and tongue never lost contact with his cock, although my hands moved to steady myself by holding his thighs, and his ass cheeks. For his part, Henry put a hand on the back of my head and gently encouraged me to take more of his cock into my mouth and throat. I sucked him in earnest and somewhat noisily; I think it was a turn-on for both of us.

After a few minutes, Henry reached down and signaled he wanted me to get up and stretch out on the bed. He grabbed a pillow and had me raise my hips so he could elevate my ass as I lay on my back. He retrieved the little bottle of complementary hand lotion I had conspicuously left on the night stand and, after opening my legs, reached down and massaged some into my asshole. Soon, a finger, then two, and even a third slipped inside me, while he leaned over my chest and took my nipples in his mouth and bit down on them. The pulses leaping from my tits to my crotch were electric.

If Henry was surprised by how relaxed my hole was, he said nothing. On the other hand, I was aroused out of my mind by the finger-fucking he was administering. I made embarrassing erotic noises, hoping to encourage him to do me deeper, and maybe harder. As he pumped his fingers in and out of what was rapidly becoming my pussy, I opened my legs wider, beckoning him to take things even further.

I didn't have to wait long. He got up on his knees, between my open legs. I watched Henry tear open a condom package and roll a sheath onto his incredible cock. He moved forward and leaned over me, locking his eyes on mine. "Is this what you wanted when you called?" he asked. "Oh god yes!" was my immediate reply.

"Then guide me inside you."

I reached down and found his cock, slippery with lubricant. I pulled it between my ass cheeks and rubbed its head against my opening. Fuck, it felt good. Henry let me tease myself, and him, for a few moments before shifting his weight and pushing down into me; I raised my hips to improve his access. My ass-pussy immediately relaxed and opened to him, welcoming his warmth, hardness and girth into me.

Jeezus, is there anything that feels like that initial penetration - the moment when you offer your submission to a man who intends to take his pleasure inside you? As a million feelings coursed from my ass and spread throughout my body, I gazed up at him and we smiled together. God, it felt soooo good.

Because I was stretched from my earlier encounter with Henry, and by the experience with the two guys in the hotel, his cock sunk all the way into me in the first try, the entry eased by the fingering and the multiple lubricants. He pressed himself deep, balls against my ass, and flexed his cock inside me. I lifted my legs and my thighs embraced his waist, offering him my body and my sex. He leaned down and once again sucked, then bit, my nipples. It was incredible.

Soon, his flexing hips established a rhythm, pushing his cock into me and pulling it out. Henry's thrusts were smooth and firm, with extra pressure at the end to fully seat his cock in my cunt. He also varied the angle of his penetration, sometimes increasing the pressure on my prostate. As the fucking continued, he began to lightly sweat, and I could feel that warmth and wetness on the inside of my thighs and on my chest. I felt submissive to his manliness and desires, and it felt good, I thought, to share myself with him in a very primal way.

Henry's length and thickness were rubbing my channel in all the right places, and my hands reached up to stroke his skin and play with his nipples. It was especially sensuous to reach around and put my hands on his ass and pull him into me - I could feel his muscles flex as he drove his cock deep into me. The connection between us was surreal and, after a few minutes, I began to enjoy an unusual feeling inside me. I was aroused as I might be in "normal" sex - truthfully, 'way more than that - but the center of that sensation wasn't my dick. Instead, the origin of the pleasure was definitely anal, and it was intensifying.

My dick was just partially engorged, and leaking pre-cum. While not lying on me, Henry's flat belly did rub my "clit" and I could feel that our skin there was wet. Another pass at my nipples with his teeth put my sexual arousal into overdrive and I felt my man-pussy involuntarily squeeze Henry's cock, provoking groans from both of us. At this point, I was losing control of my body as he lengthened his strokes and did me harder.

The deep fucking, combined with the sweaty skin contact and labored breathing, was bringing me to the brink of cumming without touching my dick. What I was experiencing was an orgasm like none before in my life, and I cried out the moment it began. Jizzum was coming out of my cockette, soaking the space between our bodies, but it was more of a steady stream and not a series of nuts. And the center of the orgasm wasn't my dick, or even my balls; it was definitely deep in my ass. The fact that Henry kept fucking me through it lengthened the pleasure and the ejaculation. Meanwhile, my body experienced a series of spasms, and I clutched Henry to stay in touch with consciousness. It was a heart-pounding experience.

Henry slowed his thrusts as I stopped quaking. I opened my eyes to him staring down at me, smiling. "Was it good?" he asked. I sighed and replied, "you have no idea." "You may be right," he said, "but the expressions on your face said a lot."

After a minute or so of rest, he began thrusting into me again. While not accompanied by the same building arousal as before, the fucking still felt very good, and I was anxious to give Henry the same kind of pleasure he had given me. I reached around his neck and pulled him down so I could breath in his ear, "take me... fuck me... cum deep in me." "Oh, baby," he replied, "I want to do all those things and more."

Henry lifted up slightly and pressed his damp, hot forehead to mine. As he churned inside me, our connection was intense and I could tell that his own orgasm would soon arrive. Suddenly, I felt the need for more - more connection - and I opened my mouth and closed my eyes. My hand on the back of his neck brought him down to me and our mouths joined. There was no initial peck. The kiss from the beginning was open, wet and intense, and I invited his tongue - which turned out to be as penetrating as his cock - deep into my mouth.

At that moment, I felt sexually completed in a way I never imagined. The spit roasting I had gotten earlier that morning was just an extreme fucking. This was something else. To be filled at both ends by a man who wanted me, who desired me, involved an intimate, personal surrender that was previously unthinkable. In its way, it was another kind of orgasm, but of my mind and spirit. I passionately wanted this, and let his tongue and lips take possession of my mouth as his manhood filled my cunt.

In the midst of this extraordinary moment, I was brought back to physical reality by the fact that in his own arousal, Henry's cock had become even harder, and I swear to god, even a bit longer. This incremental growth, combined with his battering strokes, managed to find a previously untouched place deep inside me. Oh, god, the pain was delicious.

It was at that point I felt his cock throb, stretching my channel, which was already tightly wrapped around him. Henry's mouth released mine as he groaned the pleasure of his own orgasm into my face, his cock and balls filling the condom - and sadly not my body - with his seed. As Henry held himself deep in me and came, I gazed up at him and imagined what he was feeling. For myself, I felt a kind of satisfaction I had never experienced before. I had made a man cum with real desire for me and my body, and not just casual sexual lust. It was incredible.

Epilogue

I held Henry between my thighs and asked him to stay inside me while he was still hard. We shared another deep kiss, coupled together, before he rolled off of me, the two of us panting on our backs. Eventually, I gathered the strength to sit up and lean over him, and removed the condom from his softening cock. As I set it aside, I bent down to put him back into my mouth and slowly sucked and licked off his juices. Actually, I was hoping he might get hard again, but two times in a couple hours - and the last one being insanely intense - meant that the only activity ahead of us was cleaning up and getting dressed.

I let Henry use the bathroom first, and soon he was putting on his clothes to leave. I washed the cum off my belly, but remained naked for a last hug and kiss. He once again asked me to stay, but I couldn't, and I watched with real regret as he went out the door.

For a while, we stayed in touch, but eventually the emails and IMs ended. Henry and I never saw each other again, and I occasionally wondered if my life was poorer for it.