First Date with Sasha

I’m always filled with a sense of shame when I go to an adult bookstore and begin my arduous search for strap-on videos. Being dominated by a confident, beautiful mistress has always been a fantasy of mine. A woman penetrating a man as if he were a woman seems to be such a taboo subject, but I can never seem to stop thinking about it. I love to fantasize about some of the corporate women at my office—my boss, in particular. She is a tightly wound, corporate woman who is rarely nice to anyone in the office. I love her confidence, her form fitting business suits, and her braided ponytail. I can just imagine her saying, “Mr. Roberts, could you step into my office?”

Of course, I comply. As I walk in, she says, “Shut the door and have a seat.”

I sit down unsure of what I’m being summoned for.

“It has come to my attention, Mr. Roberts, that your work has been less than perfect the last few weeks. Your reports have lacked the necessary attention to detail that we’ve come to expect here at Strap-on Industries. Now, normally, I would have you fired, but I’m going to give you just one chance, and one chance only to save your job. Do you understand?”

“Oh, yes, mam. I’ll do anything, anything you say to keep my job.”

“Good. Why don’t you come over here to me—on your knees.”

I imagine myself, in my daydream, confused and unable to comprehend why should would want me to come to her on my knees, but her demanding voice is so assertive that I walk around her desk on my knees as she stands. My face is level with her beautiful black mini-skirt. Her legs are powerful, tanned, and taught with shiny, black high heels protecting her delicious feet. I look up over her ample bosom into her eyes.

“Put your hand between my legs, Mr. Roberts.”

I look in bewilderment, and manage,“But…”

“Do it, now!”

I place my left hand on the back leg of my boss, and with my other hand, I reach under the front of her mini-skirt. To my surprise, I feel a long cock-like protrusion. It is then that I know what I will have to do to keep my job.

“Now, Mr. Roberts, I think you know what needs to happen. Suck my cock.”

I lift up her skirt so that I can see the strap-on. It is a shiny, black silicon dildo. I tentatively take the tip of her cock into my mouth. I look into her eyes for approval. She looks into my eyes with an evil smile and grabs the back of my head with both hands and forces my face onto her cock.

“That’s right, Mr. Roberts. Suck it. This is your punishment for poor performance. I didn’t tell you to stop. Fuck my cock with your mouth, now.”

As I begin to suck her cock more vigorously, she roughly rocks my head back and forth commanding me onto her strap-on. She begins to rock her hips and grabs the hair on my forehead. She is now penetrating my mouth as she sees fit. Her cock violently stretches my cheeks to the side. Back and forth she goes, as I become almost breathless. My mouth is her receptacle. She is getting off on the power, and her orgasm builds.

“Oooh, yeah. That’s it you little bitch. Take my cock down your throat. You are mine now, Roberts. You’re enjoying this aren’t you?”

She slaps my face as I manage to muffle an answer. She slaps me again in the face. I am so embarrassed, but I love taking her cock. “Make me cum you little worm. I’m going to cum all over your face. Suck it harder."”

My head is now bobbing like a rotary engine. Her orgasm builds and finally, “Ahh, yes, Roberts. That’s it. I’m cumming. I’m cumming!” She clutches my face with both hands and holds my face firmly on her cock so that I can’t move. Her body begins to tremble and I look up at her face. She begins to double over in ecstasy as her orgasm rips through her body. As she orgasms, she looks into my eyes and violently rapes my mouth. I know I am hers forever.

So, imagine my embarrassment as I look through the adult bookstore for such a video. It’s not in the straight section, not in the gay section, not in the amateur section. It consumes me, and makes me think I would be a very good investigator. I literally have to look on the back of each of the videos to find what I’m looking for. I’ve become very adept at finding these videos now, and the folks that work at my neighborhood stores know me on a first name basis.

One day, I entered my favorite store and rented a video. As I approached the counter, a young girl with piercings and tattoos named Hope saw me coming. I had a strap-on video, and on the cover was a striking woman nailing a man from behind. I was a bit timid that Hope would notice what I was renting. But, I proceeded.

“Hi, Mr. Roberts.”

“Hi, Hope.”

“Wow, this is kind of kinky. Are you into this?”

“Oh, I, um, no. I, uh, just wanted to rent this as a gag for a bachelor party this weekend.”

“Oh, is that why you’ve checked this same movie out three different times?”

She had me. I looked into her eyes. She smiled at me. “It’s okay, Mr. Roberts. Don’t be ashamed. I have a beautiful girlfriend who only dates guys who will allow her to fuck them with a strap-on. She says that if they do it to her, then she should be able to do it to them. Have you ever had a woman do it to you before?”

“No, I haven’t.”

“Well, you’re kind of cute, and my friend is single. Would you like me to give her a call for you.”

I couldn’t believe it. Hope was actually willing to set up a date between her friend and me. Just thinking of the possibility of my first actual experience was exciting me. Hope picked up the phone and dialed. “Here, I’ll call her right now. Hi, Sasha. It’s Hope. Oh, I’m doing fine; I’m just here at the store. Yeah, it’s a living. Look, did you tell me the other night that you’re not dating anyone? Good. Well, I know this really cute guy who I think you’d enjoy meeting. He’s about six feet tall; he’s lean, and he has a gorgeous smile. I think he’s cute. Yes, he’s into it. Do you want to talk to him? Oh, okay.” Hope hung up the phone. “She says to be at her place tonight at 8pm. I’ll give you directions.”

“Are you kidding? She didn’t want to talk to me?”

“No, she said she trusted my judgment. Here I’ll take that.” Hope grabbed the video from my hand and placed it under the counter. “You won’t be needing that anymore.”

I stood on Sasha’s doorstep at 8pm with freshly cut yellow roses. I didn’t know what to expect. I was dressed nicely and had expected she would be, too. I could hear loud Indian music throughout the house, and I could see low lighting—candles in the windows. Sasha opened the door, and her tanned skin glistened with sweat in the candlelight. Suprisingly, she wore a bandanna to keep her gorgeous, long, dark brown hair out of her face, and she wore a white tank top tee shirt with baggy gray pants that had fresh paint on them. I wasn’t expecting her to be dressed so casually; but then again, I could hardly expect any of what would happen this night.

“My, don’t you look nice. Come on in.”

I followed Sasha in and she walked down her hallway expecting that I would shut the door. I did. With her back turned to me, she said,“You are more handsome than Hope described. The flowers are nice. Put them in your mouth and bring them to me crawling on the floor.”

I couldn’t believe what I had just heard. I placed the flowers in my mouth and got down on all fours. I crawled behind her and followed her down the hallway. Her shiny hardwood floors accentuated her very classy home. I turned a corner and entered a room where about thirty or forty candles shined brightly. The heat in the room made me sweat instantaneously. The room was decorated with white walls and white sheets, which covered the floor. Sasha stood at an easel in the center of the room. I looked up at the painting on the easel. On the painting was a woman clad in shiny black leather. The dominant woman in the painting was penetrating a nude man with her black strap-on dildo. The man was bent over on all fours as the woman clutched the back of his head and shoulder. As I was also on all fours, I imagined me as the nude man and Sasha as the dominatrix. It was quite erotic.

“Stand up. Now, get out of those clothes for me.” I stripped down to my underwear knowing full well that Sasha’s dominance was in the air. “I want to see your cock.” I took my underwear off fully exposing myself. “Now, let’s go take a shower.”

Sasha led me to her shower, and I ran the steamy water while I watched Sasha undress. When I saw her naked, my cock immediately became hard. Sasha placed her hands on my face sternly and looked me in the eye. “Do as I say, exactly as I say, and I may accept you as my lover.”

I could hardly argue that. We stood naked in the hot shower as we kissed passionately. The excessively hot water cleansed our bodies. I began to lather every inch of Sasha’s body. Sasha lathered my crotch with her hands and began stroking my cock. With the bar of soap in hand, she gently ran the soap in and out of my crack as she simultaneously kissed me and stroked my cock. She teased my asshole with her fingers, and I tensed up a bit. Sasha took the showerhead out of its holder and sprayed me clean. She bent down and sprayed my crotch and ass.

“The thing about caressing a man’s asshole is that it makes his cock extremely hard and his ball sack tightens up and swells.” She massaged my balls and gently kissed them. Sasha grabbed a razor and shaving cream. Opening the shaving cream she said,

“Yes, your balls are nice and tight just like I like them. You can shave much better when a cock is hard.”

I looked down, and she began applying the foam to my groin. I would do anything to be able to fuck this outstanding specimen of a woman, so I let her shave me bare. I was smooth all over when she was finished. I felt quite trepidatious as this welcome stranger manipulated a razor around my cock. I stood there naked, and Sasha admired her work. “Oh, yes. That looks good. You are a lucky man. I’m simply going to have to make that cock all mine. Would you like that?”

“Yes.”

“Good boy. I’m going to make that cock all mine. Say it.”

“This is your cock.”

“And what am I going to do with it?”

“Anything you want.”

Sasha laughed. “Yes, that’s right. Anything I want.” Sasha grasped my cock and led me out of the shower. “Come on. I’m going to take my cock into my studio.”

Sasha led her cock to the room we had left earlier. As I stood there naked, Sasha began to apply lubricant to her cock. She applied so much that much of it fell to the white sheets that covered the floor. I stared at the painting of the woman taking the man’s ass while Sasha applied lube to my ass as well.

“Do you like my painting?”

“Did you do that?”

“You didn’t answer my question, and yes, I painted it.”

“Oh, yes. I like it a lot.”

“Does it turn you on?”

“Immensely.”

“Do you want me to do that to you?”

“I, uh…”

Sasha laughed at my nervousness. “Have you ever had a cock up your ass before?”

“No, no I haven’t.”

“Then what turns you on about my painting?”

Sasha brought a black box toward me. She opened the box. I looked down into the box and saw a wet gray substance. “I’m going to place your cock in this plaster of paris mold and make a dildo of your cock. That way, your cock will ALWAYS be mine.”

I couldn’t believe that Sasha was actually making a dildo in the shape of my cock and balls. I felt so sexy. She closed the box around my erect penis and tightened balls.

“I’m going to need you to hold that in place. So, you didn’t answer my question.”

“I’m sorry. What was that?”

“I asked you what turned you on about my painting.”

“Oh, yeah. Um, well, what turns me on is the complete control she has over him.”

“Is that all?”

“Well, I like the power she has. You can see from the pain and pleasure in his face that he wants her power. He needs it.”

“Yes,” she said. Sasha began to touch herself. “Tell me more.” She licked her fingers and placed them on her clit. “How does he feel?”

“He has surprise in his eyes,” I said, “but he is learning to like it. The cock is burning his insides, stretching him to accept her cock.”

“Oooh, yeah.”

She was getting worked up, and I wanted to see her continue to touch herself. I kept on. “She slowly penetrates him and lets his hole swallow her cock. She remains still while his ass adjusts to her cock.”

Sasha began to rub herself faster. She lay down on the sheets and moved the fingers of her other hand to the crack of her ass. She lay in front of me fingering her met pussy and moist ass. “Keep talking,” she said.

“Now, she’s starting to push in and pull out of him. She’s got both hands squeezing his ass as she slowly takes him. She is digging her fingernails into his ass and she spanks it. He is gasping for air as the sweat begins to pour over his body.”

“Oh, yeah. I love to hear you talk like that. You really understand the control I’m going to have over you. You’re going to make me cum.”

“Oh, please cum for me, Sasha.”

I wanted desperately to fuck Sasha, but I had to stand there and hold the black box over my penis as it hardened around my cock. Sasha fingered herself and moaned loudly as she came. With fingers in both holes, her moan was long and hard.

“Oh, you dirty fuck. I can’t wait to fuck your ass,” Sasha yelled as she completed her orgasm.

It was at that moment that I realized what Sasha had in mind. My body reacted with a cold shiver as I felt the plaster of paris tightening around Sasha’s cock. Sasha stood up and grabbed the black box. She slowly removed the box from my cock and balls. I slid out easily from all of the lube Sasha had applied to me.

“Now,” she said. “Let’s make my new cock.”

Sasha took the box over toward a cabinet and sat it down. There, she began pouring a black liquid into the mold. She was making a shiny black rubber cock—her cock.

“Come over here.”

I walked over to Sasha. She produced a shiny chrome plug from her cabinet, and she sat it firmly in he chair next to her.

“Sit.”

“But, I…”

“Sit, I said. I’ll help you.”

Sasha held the plug in place on the chair as I slowly lowered myself onto it. I had never been penetrated in my ass, but I knew that this was what Sasha wanted. I grimaced in pain as the plug sunk slowly into my ass.

“Ahh, oh, my God,” I exclaimed in slight pain.

“Take it slow, baby,” she said.

That was the first time Sasha had given me any sign of affection. I was now more willing than ever to accept her plug for her. I let the gravity of my upper body weigh my ass down to surround the entire plug.

“There, now,” Sasha said. “That’s much better. Stay right there.”

Sweat covered my body as I awaited Sasha’s return. She was wearing the skin tight black leather outfit from the painting. She looked at me and laughed. “Look familiar?”

“Yes,” I said.

“So, I guess by now you’ve figured out what I’m going to do to you.”

“Yes, Sasha.”

“Are you willing to take my cock in your ass?”

“Yes, Sasha.”

“Good. Because I want your full submission. You will be a willing participant as I take your virginity. If you do this, we will be together forever. Are you willing?”

“Yes, Sasha. I will be your willing slave.”

“To take your ass, as I please?”

“Yes.”

“You will belong to me. Do you understand?”

“Yes, Sasha.”

“You will be mine as long as I say.”

“Yes, Sasha.”

Sasha revealed a strap-on harness. I knew she was getting very close to becoming the master of my ass.

“Do you want my cock?”

“Yes, Sasha.”

“Tell me how much you love your cock.”

“I love my cock, Sasha.”

“Who’s cock?”

“Your cock, Sasha.”

Sasha removed the new solidified rubbery cock from the mold. She wiped it clean and brought it to me.

“This used to be your cock. Now, it is mine.” She held the dildo up to my face. The detail was incredible. The veins were there, the circumference and length were exactly mine. “Say it,” she demanded.

“This used to be my cock, Sasha, but now, it is yours.”

“Ha, that’s right.” Sasha slipped her new cock inside her harness. “Help me fasten this.”

I got out of the chair and on my knees. I helped Sasha into her harness and tightened the straps around back of her perfect ass. Her new cock and balls were tremendous. She grabbed it with both hands admiring it. As she stroked it, she said, “Oh, this feels so good.” With her hand, she clutched the hair on my head and guided my face to the head of her cock. “You know what to do.”

I looked up into her eyes and opened my mouth. When her eyes met mine, she smiled and then pressed my head down onto her new cock. It was what I had always wanted. I was sucking her new cock. I guess it’s the closest I’ll ever come to sucking my own cock. I only wished she could truly release all over my face. I couldn’t stop sucking her off. She loved the power, and I loved the submission.

Sasha playfully pulled out and slapped me about the face with her newfound cock. I smiled and then grabbed her cock and placed it back into my mouth.

“Yeah, suck it hard. Suck my cock, baby.”

I sucked and sucked. Pre-cum was dripping from me. I removed the plug from my ass without permission. I wanted Sasha to know that I was now ready to offer my ass to her.

“Ooh, good boy. Now, turn around for me.”

I obliged, and without hesitation, Sasha guided her cock to my asshole. She slowly slid the head into me. “Oh, my God. Your ass wants my cock so bad. I wish you could see your ass trying to swallow my cock.”

I couldn’t speak. I was trying to adjust to this long hard cock entering my ass. Slowly, Sasha pushed more in. “Oh, baby. That’s good. Who’s in control, now?”

“Ah, ah, oh my God. You are Sasha.”

“You’re mine now, boy. You’re my fuck toy. Do you like that?”

“Oh, yes,” I moaned loudly. Sasha was beginning to move in and out of me slowly. “Oh, fuck! Fuck! Yes!”

“Oh, that’s it, fucktoy. You are taking my whole cock, now.”

I was so aroused at being fucked by my own cock. My body began responding by moving onto and off of Sasha’s cock. I was fucking her cock with my previously unfucked virgin ass. This made Sasha even more turned on. She began to fuck me aggressively.

“Take that, fucker. Yeah. You take that cock hard and deep. Your ass is mine, now, bitch. Uhh. Uhh.” Sasha was now ramming my ass just like in the painting. I was overwhelmed as she raked her fingernails over my ass and clutched my hips pulling me onto her forcefully. She tugged on my hair and used my shoulders to begin slamming her cock into me.

“Oh,” I screamed. “Fuck me, Sasha. Fuck my ass.”

“Yeah, baby. Let’s fuck. Let’s fuck forever,” Sasha yelled. “I’m going to cum.”

When I heard that, I exploded all over the sheets on the floor. Cum rushed like floodwaters out of my cock, and it felt like lava jetting out of me. At the same moment, Sasha yelled and moaned as her body writhed, still connected to me by the dildo. I felt her cumming as I came, and it was beautiful. We both knew at that moment that we were meant for each other and that we would be together forever. What a first date!