Becoming His Woman

"Fuck... your pussy is sooo good. It was made to take my big black cock!"

He wasn't wrong. For the third night in a row, Marcus had taken me to bed early and enjoyed using my mouth and my ass - honestly, it was now just my pussy - to pleasure himself. That's not to say I wasn't enjoying it, because I absolutely was. His long cock reached places deep inside me where no other man had ever been, and its thickness stretched my channel and filled me in the most addictive way imaginable. It didn't matter if I came from being fucked, or not (although I usually did, hands-free) - what I really cared about was being taken and having my cunt filled by his magnificent cock, and his thick, warm cum. Knowing that my body had sexually satisfied him was its own reward.

It had been a strange journey to this moment. I was in Boston for business, and had hooked up with a well hung black dude named Henry whose office was nearby my hotel. We fucked twice -- once in his office, and then later the same day in my hotel room (a tale recounted in another Literotica story). I was supposed to fly on to Cleveland that evening, but the meeting there was rescheduled. Rather than return to California, I connected again with Henry and spent the night in his bed. Let's just say I was pleasantly sore in the morning.

This is where things got interesting. During breakfast with Henry, he urged me to stay for another day (and night) or two, and then started telling me about a friend of his - Marcus - who was recently divorced (from a woman) and had confessed to Henry that he might like "to try sex with a feminine man." While I wasn't physically feminine (yet), Henry noted that fucking me was a lot like fucking a woman - I was submissive and took care to make sure my partner enjoyed himself. He also said that Marcus was extremely well endowed, both long and thick, and he thought I could fully satisfy him, something that Henry suspected Marcus wasn't getting from any of the women he was dating.

The implication was clear: Would I like to meet Marcus and let him fuck me? Sure.

So... that night, Marcus was invited over to Henry's apartment.

In the afternoon, at Henry's suggestion, I took a moisturizing bath - after using an enema kit - and carefully shaved most of the body hair below my neck, leaving only a neatly trimmed landing strip above my modest dicklet. Henry returned home with a lacy thong that fit me snugly, along with a pair of silky thigh-highs and a short silk robe. He also had me put on some dark red nail polish for both my hands and feet, and a matching lip gloss. There was no way I was going to pass as a woman, but I was intrigued by how feminizing just these few grooming changes were, and how they changed how I felt about my body.

When Marcus arrived, he and I were seated together on the sofa, and Henry brought us all generous glasses of wine. It turned out that Marcus was an educated conversationalist, and he seemed to enjoy my company. Well into a second large serving of wine for all of us, I began reaching out and gently stroking Marcus -- first his arm next to me, then his thigh. Soon after Marcus put his arm around me, and with his other hand, began stroking my thigh through the silk robe while we continued to talk. After 10 or 15 minutes of becoming comfortable with each other's touch, I turned slightly into Marcus and moved close to his lips; but he seemed resistant to kissing me, so I nuzzled his neck and shoulder. Marcus did expand his explorations of my body - rubbing both the bare skin of my thighs and that part covered with silky stockings, as well as squeezing my ass cheeks. It was a turn-on for both of us.

Through all of this, Henry remained a voyeur; actually, his presence was a bit of a turn on for me -- it seemed a bit naughty to be so intimate with his friend right in front of him. Eventually, Henry suggested that we move things to the bedroom, which was already dimly lit with candles.

I laid down on the bed while I watched both Marcus and Henry get undressed; they then joined me nude on either side. I reached out and gently grasped each of their already hardening cock. Just a few strokes brought both of them to full erection, and oh my god, was it impressive! As I mentioned, Henry was well hung - at least eight or nine inches, and medium thickness; he had a beautiful cock. But Marcus was literally breathtaking: His cock was immense, at least 11 inches long and very thick. It was both scary and incredibly arousing.

At its cut tip, Marcus' cock was already leaking pre-cum; that signaled to me that I needed to slither down and take it, and Henry's, into my mouth. I got in position between them, and alternated between the two of them, practically drooling on their cocks as I sucked them. Henry's cock was big, but Marcus' required stretching my mouth wide open and worshiping just its first three or four inches with my tongue and lips. They both tasted great.

After becoming achingly hard, Henry disengaged himself, got off the bed and walked over to a dresser, where he retrieved a tube of lubricant and a bottle of poppers. When he returned, he got us organized to take it to the next level. He had me remove the robe and assume "the position" towards the end of the bed on my knees; he then slid in front of me so that his cock was directly below my mouth. He handed the lube to Marcus, who moved behind me, pulled the thong down, and began drizzling it between my ass cheeks. Using his thumb, he spread it around my asshole, and then squirted a long squeeze into me. After that, I heard the sounds of a cock being well lathered. Meanwhile, Henry opened the bottle of poppers and thrust them under my nose, saying "you'll definitely want to take a long hit on these -- you need to be very relaxed for him." I did as I was told.

The poppers had an immediate and overwhelming effect. In addition to the usual rush, I suddenly became even more aroused and horny, and all I could think about was having my ass filled with a huge cock. And that's exactly what Marcus was going to give me. I felt his cut tip press against my opening that was blossoming under the direct effect of the poppers. He gently pressed forward - or I pushed back, hard to tell which - and his cockhead and a couple of inches of his incredible mantool moved into me.

Fuck!! One of my favorite parts of bottoming for a hung top is that first penetration; it's like losing my virginity all over again. But this was something on a whole 'nuther level. Marcus' cock was huge and the pain of being stretched open was serious and delicious. I held my butt steady as he slowly probed back-and-forth, moving his manhood deeper into me. I had never been fucked by anything so large.

As Marcus continued his penetration of what now was - for him - clearly my pussy, Henry reached down and grasped each of my large erect nipples between thumb and forefinger and pinched them hard. As my mouth opened in surprise (and pleasure), Henry took my head in one of his hands and guided my mouth down to his cock. I immediately understood what was expected of me, and sucked his dick deeply, its head nearly entering my throat. His hands returned to pinching and twisting my nipples, further arousing me as Marcus pushed himself even deeper.

This was the first time I had ever been spit roasted, and to be done by two so well endowed men was incredibly thrilling. And at this point, Marcus was not even all the way in. Sensing that I might need to be even more relaxed, Henry grabbed the poppers bottle and again pressed it to my nostrils. I took another big hit, and was literally feeling no pain - just an overwhelming desire to be filled and fucked. But to do that, Marcus needed to push his incredibly long cock past the bend into my intestine. The combination of the poppers and small gyrations of my ass, changing slightly his cock's angle into me, suddenly got him through. His black and wiry pubic hair was now pressed against my white and soft skin; I had taken all of him.

"That's incredible," Marcus exclaimed. "I've never been balls deep in any woman. The feeling is insane." I glanced back over my shoulder and saw his expression of pure pleasure, and I can't tell you how proud that made me. Before putting Henry back in my mouth, I told Marcus to remain still, and let me work my asspussy open for him. He held me by my waist, his fingers and thumb gently rubbing me as I moved slowly back-and-forth on his cock. It was almost sweet. Inside me, his thick cock had me stretched to the limit, but I could slide it in and out by an inch or two, and then more.

Once again, I took Henry's cock out of my mouth, and instructed Marcus to slowly pull his tool out of my pussy, then put a long squirt of lube directly into me. I also asked Henry for another hit on the poppers; honestly, at that moment, I was almost delirious, but I really wanted to be fucked and I needed help for that.

Barely hanging on to consciousness, I turned again to Marcus and said, "I want you to push your cock all the way in, and then I want you to fuck my brains out." I hungrily took Henry back into my mouth, with a plan to have him throat fuck me once Marcus got started. I had never been so horny in my life.

As Henry's cock moved between my wet lips and over my tongue, Marcus once again pressed his huge dick into my pussy. Between the poppers and the lubricant, he slid right in, although that description doesn't do justice to the rush associated with the rapid expansion of my channel by his girth. I swear I could feel the crown around his cockhead and his pulsing veins along the thick shaft. He kept pressing, and towards the end of the stroke, was slowed only momentarily as his cockhead turned the corner into my deepest recess. Oh god, oh fuck, he felt so good as he pressed up against my ass cheeks.

Marcus now took control of our sex. His hands tightened around my waist and he used that control to begin pulling me off and then pulling me back on to his magnificent cock. Within a couple strokes, he was moving smoothly between being fully inserted in my cunt and pulling out to a point where only a couple inches of his shaft were still inside me. His thrust felt almost magical, firm and penetrating to my core, rubbing over top my prostate, and then into my previously unexplored depths. It was an amazing fucking.

At the other end, I relaxed my throat and pressed my mouth forward towards Henry's crotch. The poppers did their job and his cock moved into my throat; I didn't stop until my nose was pressed into his pubic hair. At that point, I had nearly two feet of cock inside me and I was feeling like the ultimate sissy slut. All I wanted to do was please these two men and their amazing manhoods, and that's exactly what I did.

With my pussy stretching, and becoming a bit looser, I could now move my ass with sexual purpose and occasionally clamp down on Marcus' cock as it moved in and out of my channel. I couldn't look back because I had Henry's cock deep in my throat, but I could hear both men groaning with pleasure and grunting with exertion. The three of us found a perfect rhythm as I took their entire cocks into my body with their alternating thrusts.

While I was determined to pleasure Henry and Marcus, in fact I was the one on sexual overload. So as it became clear that their orgasms were approaching, I realized I was on the verge of an erotic explosion. I tried to keep focused on their cocks, but when I felt Marcus suddenly become even harder, and start to throb, I knew I was lost. As Marcus shot his first large load of cum deep into my pussy, it triggered my orgasm, which in turn had me sucking hard on Henry as he began to cum. While not exactly simultaneous, at some point our orgasms -- all soul stirring -- overlapped and I momentarily lost consciousness. I felt Marcus collapse onto my back, his manhood still lodged deep inside me, as I finished sucking all of Henry's cum from his cock and balls. I pulled my mouth mostly off of him and lay my head on Henry's thigh.

I think we all relaxed on that bed together for at least 10 minutes, trying to recover from what was easily the most intense sex of my life. Judging from the sounds, and then simple sentences that both Henry and Marcus began to string together, they were very satisfied. I had fulfilled my purpose as a feminine bottom and it made me happy.

Henry disengaged himself first and offered to get us something cool to drink. While his cock remained in my guts, even after it softened, Marcus eventually withdrew from my pussy, but not before gently and affectionately stroking my ass. He got up and, after wiping himself off with a towel, got dressed. Before leaving, he expressed his deep appreciation to me and told Henry that he would call him tomorrow.

Little did I know how radically that conversation would change my life.