We sat in the box seats along the third base line at Fenway Park, watching the Red Sox pulverize the Yankees. It was the seventh-inning stretch, Sweet Caroline was playing loudly, the fans were singing to it, and Stephen and I had just bought Polish sausages.
As I took my first bite, he leaned over, and whispered, "You could probably take in that whole thing, couldn't you?"
I smiled. I knew he was referring to last week, our first date, if you wanted to call it that. We had met after I answered his online ad, both of us being married bi-guys who wanted to try out a sub/dom gay relationship. For newbies, it had gone pretty well, or well enough, I guess, because here we were today at our second meet-up. After the game, we were going to be going somewhere special, Stephen had promised me, but not to where, nor for what.
When the last Yankee flied out, we filed out along with the other thirty-seven thousand jubilant fans. We moved slowly, with the throng, to his car and drove off into an area of Boston that I'd never before been. We strolled down Ellery Street and through the door of Silks and All That Ilk, a dress shop that catered to men. Our sales person introduced themself with their preferred pronouns and asked us what we were looking for today.
As I stood there stunned and speechless, Stephen took charge. "I would like a lovely evening dress for my girly boyfriend."
Erika, our sales person, eyed me approvingly, and walked us over to a rack of tight-fitting dresses with lace in various places and spaghetti shoulder straps, cut, apparently, with a broader chest for a cross-dressing man. I was shown the fitting room, took off everything except my briefs, and put one dress on, walked out to look and be looked at, blushing all the while. After trying on two more, which didn't meet with Stephen's approval, the fourth one clearly did. I saw him in the mirror's reflection nodding, his tongue licking his lower lip, as he nodded to Erika that we would take it. We were shown a pair of matching shoes, which Stephen also bought. I was still flummoxed by this surprise shopping trip, but what I learned from my last time meeting with him was that when I was in his house, I did what he wanted. Now I wondered if that extended to when I was in his car and whenever I was in his presence. That thought was met with anxiety, but it also thrilled me. I sensed a power dynamic. I gave him the power to tell me what to do, but my obedience turned him on, and gave me the power of seduction.
We left the store and walked down the block back to where his car was parked, passing a shop called LeatherFolk on our right with flogs and other bondage paraphernalia displayed in the window.
"We'll visit that shop sometime," Stephen stated nonchalantly. I swallowed hard.
We ate dinner at his favorite fish place, and talked cordially, about the game, about work, and about other things, none of which had to do with our visit to the dress shop.
When we returned to his place, as he unlocked the front door, I inquired,
"When will your wife return tonight?"
"That was a little white lie I told you last time. I'm no longer married. I just didn't want you to have any expectations about staying the night."
"What about tonight?" I entreated as he opened the inside door, and we stepped inside.
He shut it, locked it, turned toward me, put his thick-fingered hands on my shoulders, and, with his massive frame, pushed me up against the door.
He stared into my eyes, "If you are a good little girl, I will permit you to stay the night with me."
"Thank you, Sir," I heard myself say, though a bit falteringly, the familiar thrill of his domination beginning to weaken me in my knees.
Then he let me go, stepped back and said, "I want you to, how do the ladies put it, 'freshen up a bit,' so you can put that dress on when your body is clean everywhere. And I mean everywhere. I'm gonna shower first. You can go after me. There's a spare bedroom where you can change. And let me get you a razor. I want you to shave your legs, and put a cream on them after you've showered."
"Yes, Sir," I tried to enthusiastically signal my agreement, as I tamped down any fears of what might be asked of me next.
While he showered, I undressed in the spare room, and hung my new garment over the curtain rod, putting the low-heeled shoes beneath. I wrapped a towel around my waist and waited. I didn't know where this relationship was going, as trepidation kept warring with titillation.
Minutes later a knock came on the door, Stephen announcing that it was my turn. I walked into the bathroom, with its mirror fogged-up from his shower, and assembled what I would need in the stall. Never having done this before, I tried out various methods and finally succeeded in shaving my insteps and calves up to my mid thighs. I washed the rest of my body concentrating on what Stephen probably meant by "everywhere," shampooed, and then rinsed off. I dried and put his rose-scented cream on my legs.
Back in the spare bedroom, using the full-length mirror, I put on my new gown, turning first one way and then the other. In the privacy of my room, without any potentially disapproving eyes, I marveled at how the dress defined my broad shoulders and sculpted my waist and hips, while accentuating my tight ass. And that slit up the left side, a very alluring feature, showed off one of my newly shaven and gleaming legs. The low-cut neckline, revealing my pecs, and the scooped back gave anyone an exquisite view of my torso. But perhaps the most striking feature to me was the sheen of the deep blue color, making my eyes all the more lustrous. With poise and confidence, I exited the bedroom and strode the hallway to the living room.
And there he was, standing, patiently waiting, and now intently ogling, in a pleated white shirt, a gold chain nestling in his chest hair between the collar opened several buttons down, and contrasting black slacks and shoes. He looked irresistible, massive, and manly.
"Come closer," he beckoned, "and turn around. Let me see you in this light. That dress makes you look stunning, you know." And with a silky voice, he inquired, "May I have this dance."
His demeanor was different, he seemed smitten in a way, and suddenly more gentlemanly, polite, asking my permission, rather than demanding what he wanted. I didn't know what to make of that, but I didn't have time to wonder, as he went over to his sound system, and turned up the next BB King song. He offered his hand, and I took it.
We began moving back-and-forth to the rhythm, grinding the way high school students used to dance a slow dance, his leg in between my two--as much as it could go with my tight dress—but clearly his hip was full against my groin. I felt his hands gently caress my back and then make their way slowly down around my ass, the silky fabric letting him glide easily over and around my buttocks as he pressed his pelvis into my groin. Suddenly he exclaimed, "Going commando, now are we!" I felt him respond by tightening his embrace and bouncing me more wildly to the beat, singing along in a rasping bass. He brought his lips down and began pressing them into mine, first one way then the other, trying to find our perfect fit. Surprisingly gently, his tongue began to probe the crevice between my two lips, and I pressed my tongue forward in greeting, before allowing him full access to my mouth, his tongue gliding along my upper gums, then lower gums, in circles. My little squeak of excitement brought more of his tongue, and soon he was plunging it into my mouth in rhythm to BB King's Rock Me Baby, and my pelvis was beginning to quake.
On impulse, I pulled away and whispered into his ear, "Please talk dirty to me, Sir." Bad move, it turned out.
He stiffened in rebuke, admonishing me, "I shall be Sir Stephen to you from now on, you fucking whore, and never, ever tell me what to do. Is that clear?"
"Yes, Sir Stephen," I verbally groveled.
He maneuvered his lips over my cheeks, along my jaw bone, and down my neck, with growls and nibbles that were just below the threshold of painful. Although his tone became gruffer, he did give me what I wanted, which was what I had intuited he wanted, but just hadn't suggested subserviently enough. Nevertheless, it really ratcheted up the emotional tempo.
"You are the cunt I knew you were. You nasty, shameless bitch. You have a lot to learn, you whore. I'm going to teach you by fucking your pussy-hole tonight, because I want it, and I can."
As the music continued on, so did we, doing circles, grinding more roughly now, and slowly eddying toward the kitchen.
"I'm gonna take you across the kitchen table, bitch. That's what you want, isn't it, to be hot-fucked on a cold table top?"
"I am here to serve you, Sir Stephen, in any way you desire," I improvised, a little trickle of sweat now running down my back.
"Fuckin' right, cunt hole."
When we reached the linoleum, he stopped moving. "Undo my fly, you slut, and get me out."
With trembling fingers, I fumbled with his zipper and snap, pulling his pants down, then his boxers, and liberated what was now a thick dick pointing to the ceiling.
"Take me like I wanted you to take that sausage today," he commanded.
I lathered up his rigidity with my frothy saliva, and I descended on him with lips first, then pulled my mouth out letting my teeth gently graze his shaft.
"Ooooh," he hollered, affected by my sensual sucking, "That's extraordinary, you cunt-hole! I've never had that done before. You are becoming worth every fucking penny I paid for that fucking dress."
I was getting harder too, but kept my attention on his meat.
"Now I'm going to fuck your cunt-ass, bitch," he said, and instructed me to pull out a condom from the pocket of his trousers pooling around his ankles. As I tore it open, at his direction, he ordered, "Put it on with your mouth."
I didn't know how to do that, but somehow, I managed, with the help of my hands to get it onto his glans, and then, using my lips and teeth, I unrolled it down his entire shaft. He now had a BBC: big blue cock.
He pulled me to standing, turned me around, and forced me down, face first, on the kitchen table. He hiked up my dress from behind, reached for the olive oil on the counter nearby, and commenced to pour little drips onto my ass. Suddenly, I was worried about the oil ruining the dress, so I pulled it up the rest of the way, above my waist, and laid my chest down upon it. My cock, good and hard, and my sac, were now on the cool kitchen table beneath me.
As he continued to lubricate my ass with his fingers, I spread my legs to accommodate him. I had this anxiety about the first-time being butt-fucked. I had had a butt plug up my ass, and variously shaped dildoes, all of them intensifying my erection and sometimes even making me come immediately, as the sensation combined with cock stroking was so euphoric. But all such objects were relatively smaller in girth than Stephen, and, even so, some of them had been painful on that initial insertion. So, I had some dread of what a beastly gorilla Sir Stephen would be like, especially after I had angered him minutes ago with my insubordination. He might want to show me his dominance again, but this time by being an ass-wrecker. Still, I craved that anal- fucking euphoria, and from a real man, not from a hand-held piece of plastic. And that lust-filled fantasy now replaced any lingering fear, thankfully, because he was actually taking his time, stretching my anus, kneading my buttocks and rubbing the insides of my thighs, even as he continued his verbal belligerence.
I felt the initial pressure of his cock head against my anal bud, with the weight of him leaning into my thighs. "Are you ready, my slut. I am claiming your pussy-ass for tonight. For tonight and forever. Do you understand this, you bitch?"
"Yes, Sir Stephen," I gasped as I felt the increased pressure and a sharp pinch. I screamed, but in seconds the intensity of pain had given way to the divine pleasure of stretch. His rhythmic filling and fullness, his weight pressing on top of me as he pumped in and out from behind, all replaced the initial sting.
"Oh, you are so fucking good to fuck, so fucking tight," he exclaimed, as he increased his tempo, each thrust putting more weight into me and with it, edging the table closer and closer to the wall. When it could go no further, his entire weight was transmitted into me and I felt the full power of this man, to whom I was willingly surrendering.
I spread my legs more, as much as I could, and reflexedly attempted to meet his every thrust with my own upward pelvic rock. The friction of the motion was causing my cock, squeezed between the table and my abdomen, to tingle, like I would come any moment.
I heard Stephen grunting the same message, "I'm coming," and that was all it took, him erupting into me and me erupting all over the kitchen table.
Stephen collapsed, crushing me into the wooden table top. He outweighed me by 80 pounds, and this hot and heavy body on mine was both constraining and comforting. I had turned him on. I had excited him to the point where he had fucked me. This was a new power I had experienced, and I wanted more of it.
But first, I had to breathe. "Sir, Stephen, if it pleases you, would you mind easing off me just a little?"
By the time I had inquired that of him, he had grown flaccid, so that now his cock was beginning to loosen in my anal ring, and I felt it delightfully, but regrettably, slide out. Obviously satisfied, he put his hand on my ass cheek, gave it a little squeeze, then slid it up to my back, then to my neck, and over to my shoulder, with which he hauled me up.
Looking me squarely in the face, he feminized my name with the invitation which followed, "You are my beautiful-to-fuck ass-cunt, Martha. You may spend the night."
As I recall what followed, in my completely altered state, we walked into his bedroom, Stephen behind me with his strong hands on each of my shoulders steering me there. We got undressed in front of each other, took turns taking a piss in the master bath, brushed our teeth, but all the while in relative silence.
I had just given my virgin ass hole to this man. It was not in a tender and loving way, like how I would imagine a bride giving her virgin vagina to her loving husband on their sacred wedding night. It was more like rough romanticism, animalistic arousal, seasoned by raunchiness, vulgarity, and uncensored crudeness. And yet, the feeling of my first time, with a real man shoving his really big dick into me seemed really special. Yes, it was raw carnality with a relative stranger, but someone who I actually seemed attracted to. And it was with a man who I felt was equally attracted to me, who wanted to fuck me as badly as I wanted to be fucked by him. Someone whose passion for me I had ignited simply by clothing my body in women's wear, and enticing him to talk dirty to me. And now, the afterglow felt great. No regrets. In fact, I wanted to be fucked again—once I was sure my anus was going to recover its tight tone, and the soreness I felt, would completely resolve.
The whole experience exhausted Stephen, I think. At first, I thought that playing the dominant role was taxing for him, and maybe it was. But when lying in bed next to me, close to passing out, he babbled, "I like how we are together, Martha. I don't see things with us going the way they did in my two marriages. Both of my exes left me because, they said, they didn't like what I had become. But you seem to enjoy it."
"Become what, Stephen? Enjoy what?" I had inquired with genuine curiosity, tinged with a little worry.
But only his soft breathing followed, as he had fallen deeply asleep. Oh, well, I thought. Probably something having to do with women, and not likely to be a problem for two men. Still, I resolved to inquire about it in the morning, and I, too, relaxed into slumber.
I awoke to a freight train rumbling through the back yard, or what I thought was a freight train. It turned out that it was Stephen on his back snoring loudly. Although I tried to breathe meditatively to put myself back to sleep, the irregularly of his respirations made it impossible for me to settle. I had no other choice but to elbow him gently in the ribs. He awoke, or partially so, turned over toward me, pushed me onto my right side, and put his left arm over my left shoulder and cozied himself up against my naked back. The snoring stopped, but Stephen didn't. Either he was sleep walking —or sleep fondling—or else our skin-to-skin touch had aroused him to arousal. His left hand began massaging my groin and I, in turn, became turned on. Stephen, in his sleepy deep voice, reminded me that I was his anal slut, which meant anytime he wanted to fuck me, he could, without asking my permission.
"Isn't that so?" he asked.
I recalled our intercourse the previous night, where he claimed my ass for himself, as he was about to pound me from behind. I was so delirious with anticipatory pleasure, that in my altered state, I think I had assented, more to lose my anal virginity, rather than with an actual rational handshake agreement. My ass was still a bit sore, and I wasn't exactly sure to what I had agreed, being in a more sober moment like now. Or, at least, I had been in a more sober moment, moments before now, because my arousal was taking me out of the realm of rationality, and into the state of sensual and, once more, seductive surrender.
"Yes, Sir Stephen, I am your cunt hole to use any time it pleases you."
I could feel his thick cock poking into the crease between my ass cheeks, and his heightened excitement further aroused me to the point where now I felt only one thing mattered: to allow our mutual pleasures to be co-mingled again in this new moment.
Stephen got up on his knees, and in the glow of the street lights shining through the windows, I could see him fully erect, all six inches of him. With a hand on my left shoulder, he pulled me onto my back. With his right hand, he opened the drawer of the nightstand, pulled out a lubricated condom, put it on, and said what he said to me last night, right before he was about to enter me, "Now I am going to fuck you, Martha," substituting my newly christened name for what he had called me last night. And then the gentleman in him politely, but snidely, added, "That better be OK with you, because your pledge has already been given to me."
To which my only answer was, "Yes, Sir Stephen. I am yours to do with as you wish."
He put his hands around my ankles and hoisted my legs up over his shoulders as he leaned forward to enter me. I was doubled over with only my head and shoulders resting on the pillow, but able to maintain the Kama Sutra pose with my legs hanging off his torso. I felt his cock jabbing around my back door, searching in the dark for my anus. Mercifully, he finally used one of his hands to locate the entryway, and the other to place his cock tip there.
Then as I gasped "fuck me, fuck me, fuck me," he fucked me over. For what seemed like minutes, he lingered there, teasing me, and maybe teasing himself, before I felt the welcome stretch of his thick condom-covered cockhead. To my delight there was no pinch this time, only the rapturous feeling of stretch, and of him crashing into me, his balls slapping my buttocks in rhythmic grunting strokes. As he fucked me, I spit into my hand, reached down, and begin encircling my own hardness, rubbing it in time with his thrusts. Because it was in the middle of the night, this was not going to be a long, drawn-out affair, I figured, as he began ramping up the tempo, pounding into my ass, and breathing heavily. I came first with a loud scream which I'm sure rang through the walls of the house and maybe reached into the streets outside. He covered my mouth with one of his hands as he also let loose a loud grunt and several, "Ahhs," in between gasps for breath, pumping his load into the condom covering his cock inside me. Finally, after several expressive sighs, he gently removed my legs from his shoulders and laid down on top of me. With the comfort of the mattress beneath, and his heavy, still panting, hairy and naked body on top, I was swaddled in a post-orgasmic sandwich. We lay there quietly breathing together.
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