He Nows Me Better Than I Now Me

This started a few years ago. Chrissy and I lived in the same apartment complex. I'd visit Chrissy's apartment once in a while, typically after she texted me that she wanted to watch a movie with someone or something like that. She was tall, thin, had dark green eyes, dark brown hair that contrasted well against her pale, light skin, and a little bubble butt and small set of perky breasts. I was clearly stuck in the friend zone with her, but I still masturbated to sexual fantasies with her.

Once in a while she'd get drunk, and tell me about BDSM related things she did with some recent guy or that she'd like to try and end up passing out, leaving me crazy horny. I never acted on it or brought it up though. One time she acknowledged my endless patience with her though. We were both drunk on New Year's Eve, just after the ball dropped actually. She said something along the lines of, "you're always such a gentleman, never taking advantage of me."

I just chuckled in response, unsure of what to say, just thinking to myself that this is probably why I was always in the friendzone. Alcohol apparently didn't make me any better at talking to girls.

She told me, "take these off. I want to reward you," tugging my pants.

I felt really nervous, unzipped my jeans, and slowly pulled them down. I started blushing immediately. I could only see her smiling and looking downwards. She pulled my boxers down herself and saw my flaccid penis. She grabbed it and started stroking it slowly with her hands.

"Get it hard for me. I want to see you hard," she demanded, as she let go of my penis. I grabbed my penis, and started desperately trying to stroke it while thinking of her naked, but it just made me feel more anxious.

She then taunted me saying, "don't I turn you on?"

"Definitely, I guess it's the alcohol making it difficult..." I quietly said, half mumbling. "I want to see you naked," I admitted.

Then she pulled out her phone, and showed me a picture of her ass, looking very red like she had just been spanked a lot. "You like that? Mm hmm."

I started to say, "yeah, that's hot-" but then she showed me another picture of her holding this guy's penis while kissing his abs smiling. She was only wearing panties, but the picture was too small to see her breasts as they were partially covered up by the way she was posing. The man in the picture was someone I vaguely remembered her talking about before, but couldn't place his name. I just knew he fooled around with Chrissy off and on, but they never had a serious relationship. He was black, fairly athletic and tall, and apparently well hung.

I felt a little gush go to my penis. I looked down, and Chrissy followed my eyes and we both noticed my penis had gotten a little harder. Chrissy laughed out loud, and then said, "sorry, I'm tired anyway. I didn't mean to tease you."

She shortly went to bed, passing out. I felt a little awkward, and left to go back to my apartment.

As soon as I entered my apartment, I got a full rock solid hard-on and masturbated to the two photos I had just seen, despite the humiliation I had just experienced at not being able to get hard at all.

A few weeks went by, and the topic never came up with Chrissy. However, one day I was leaving my apartment, and I looked up and realized I saw the person in the photo in the parking lot.

I looked at him, and he noticed. He yelled, "Daniel?"

"Yeah?" I asked.

"What's up? Remember me? Chrissy's friend, John."

"Oh yeah," I remember meeting him one time in a similar situation except Chrissy was with him walking to the parking lot. Surprised he remembered my name.

"I meant to see her, but she ain't here. Mind if I use your restroom? Or did I catch you at a bad time?"

"Sure, no it's fine," I said, a bit nervously, having seen a picture of his penis. I saw he had a six pack of beer in his hand.

We walked inside together. Before entering the restroom he said, "I know you and Chrissy are good friends. I think that's cool." He handed me a beer.

"Right," I answered, wondering why he's here.

He was in the bathroom for a couple minutes.

He got out of the bathroom, and said, "listen, I don't want to beat around the bushes. Chrissy told me you're into dudes." He gently put his hand on my shoulder and forced me to sit down, as he sat down next to me on the couch, and put a hand on my leg. And he continued, "and seeing as how she ain't here and it's been a while since a white boy choked on me... you see where I'm going with this?"

My face turned red, and I could barely speak. I just said, "she said that?" I felt butterflies in my stomach.

"Yeah, are you denying it?" he demanded to know.

"No," I asserted. But then questioned myself, "Well, yeah. I've never even thought of being with a guy!" I felt a little annoyed at Chrissy.

"You've been hanging out with Chrissy all this time, and never banged her?"

I was silent. John chuckled briefly and looked down. After a brief silence, he said, "relax."

John had a beer, and took a good chug of it and looked at me. There was another awkward silence, and he apparently took it as his cue to proceed, and stood up and proceeded to pull down his pants and boxers together. His flaccid penis was several times bigger than my hard penis. I'm about 5" long, give or take, his was almost twice as long it felt like. It's one thing to see a picture or something in porn, but altogether different to see a huge penis in front of your face. I felt myself intensely turned on, and let out a deep breath but tried to suppress it. He took a step to be as close in front of me as possible.

I tried to avoid staring at his penis so much, awkwardly, but he simply said, "you can look at it. Touch it."

I just replied, "it's so huge." This put a grin on his face.

Then I added, "I don't know if I can."

Then he responded, "let me make this easier for you. Get on the floor!"

I hesitated for a moment - I was not prepared for this. But I then obeyed, watching him look at down at me. He grabbed his penis in his hand and lifted it, and said, "don't just look at it, let me get you started" Then he let go of it, while leaning forward a little, and let it smack against my face, and then he grabbed it at its base and smacked it against my face a few more times, until I opened my mouth, and stuck my tongue out a little, and right then he grabbed the back of my head and pulled so that I now had my tongue against his balls, and his penis was facing upwards, leaning against my face.

It was very aggressive at first and I tried to resist, but he held my head tight against his balls. I finally gave in and started licking.

"There we go," he said. I licked everywhere, swirling my tongue around them and then tried sucking each one. He added, "I'm going to make you my bitch boy."

Then he aggressively pushed his penis down onto my tongue with his free hand and then thrusted it into my mouth just a little. He pushed and pulled my head repeatedly, developing a rhythm, and then let go. I continued the motion, and grabbed his penis to guide it. I could barely fit anything beyond the head in my mouth, and loved it.

I finally gained a little courage, and took his penis out of my mouth for a second, just so that I could lick up and down the length of the shaft, admiring how long it is, before putting it back in my mouth and bobbing my head back and forth on it. I let out a soft, long moan in the process.

My penis was so hard at this point, I felt like it wouldn't take much to erupt a ton of cum in my pants at any moment. I gagged a little, trying to test my limits, and my eyes became watery. He pushed my head back towards his balls so I started licking them again, while now he started stroking himself. He started speeding up, and said, "hope you're ready bitch boy," as he pointed the tip of his penis lower. I took that as an indication to open my mouth for him. I opened, and placed it just at the tip of the head ready to catch everything. I heard him grunt, and a moment later I felt hot, salty semen enter my mouth one gush after another. I swallowed everything that came out. He continued to stroke it for a few seconds, and I continued to get as much of his head in my mouth to catch any last few drops. I paused to swallow, and then could feel it soften, but didn't stop until he backed up from me.

"Been a while since I've gotten head from a white boy, I wasn't sure if you'd be up for that," he said.

"How'd I compared to Chrissy?" I laughed, asking nervously.

"Not as freaky as her," he calmly said.

I chuckled, still on my knees. He put on his pants.

"Do you want to keep the beer?" he asked.

"Uh, leave one or two bottles," I answered at the unexpected question.

He took his beers, and left, just like that.

A few days later he sent me a message on Facebook. He asked, "wanna come over?"

I procrastinated for a couple hours, but finally I said, "sure."

Within maybe 30 minutes, he gave me an address.

I showered, and went over. It was just a 10 minute drive I think.

He answered the door in gym clothes, and handed me a beer right away. Same type of beer as last time.

There was some small talk at first. But finally he interrupted the small talk when I had almost finished the beer and said, "so I figured we could continue where we left off."

"Yeah?" I quizzed.

"So are you into dudes?" he asked.

"I don't know," I said, avoiding looking at him. I think he knew the answer by now. But then I turned it around on him, and asked, "are you?"

"Yeah, some... feminine guys mainly."

"Am I.. feminine?" I asked.

"Don't take it the wrong way, but yeah. I'll be right back."

He went into a room, and came back with some clothes. "Try these on, Chrissy left them here a while ago. You can change in the bedroom if you prefer, don't feel embarrassed."

I went to the bedroom, and took my clothes off and placed them onto the bed. It was just black panties and a white tee shirt with some logo on it. I put the panties and the tee shirt on. I admittedly liked the way they felt on me.

I was going to return to the living room but John came in at that point. He said, "turn around, show me how you look."

I felt him squeeze my ass, and then rub and move his hands up and down my hips.

He said, "see, you got a nice feminine figure. You might even fill out these panties better than Chrissy." I felt him press his body against mine, and felt his penis harden against my butt, giving me goosebumps.

He turned me around to face him again, and wrapped his hands around me to squeeze my ass some more. Then he pulled the tee shirt off me, and said, "now only if you had some tits."

Then he squeezed what little there is of my chest to squeeze, and put his mouth over my nipples, sucking them.

I felt very girly at this point obviously, and felt like putty in his hands, just letting him do what he wants with me. He gently pushed me on the bed. I didn't want to say anything but I wanted it bad, I wanted him to ravage me. It didn't occur to me my dick was as hard as could be but got no attention, and I was perfectly fine with that.

He motioned for me to flip over, so I was laying down on my stomach. He reached into his nightstand for a moment, and put a condom on and some lube I presume.

He got on top of me. I felt him kiss my neck a little from behind. He grabbed my waist and pulled me so that I was bending over now, rather than laying down. One hand smacked my ass a little, while the other moved the panty area covering my anus to the side. I felt really nervous just anticipating some possible pain. I didn't want to say anything because I was so eager to experience it though. "Relax," he said.

I looked forward. I think he hand one hand guiding his penis towards me. I spread my ass with my hands for him, ready. I felt the tip rub against my ass, then move right into my anus, and with a slight push, it was in. I felt a surge of both pleasure and pain. He seemed to pause for a moment so I could adjust to the stretching, and then started to thrust himself into me. I was overcome with pleasurable sensations from the motions. He went faster and faster. I moaned involuntarily with pleasure. I had never felt so intensely stimulated.

He re-assured me, "it won't hurt as much next time."

It did hurt, but it was also re-assuring to hear him say "next time."

He started going real fast, and his balls were slapping mine a little. I heard him make some noises, and then could feel the sudden pulses in me. I didn't cum, but never the less I felt a glow during that moment.

He pulled himself out of me slowly. The last bit of his penis leaving my body felt strange. He smacked my ass another time, and turned on the shower.

"Looks like Chrissy has some competition," he said with a chuckle.

"Yeah," I replied. "I've never done anything like that."

"I know, but I bet it won't be your last," he responded.