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Best friend's sexual frustration transforms Alex.
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CD transitioning ready for cock t4m 22 (Bum Fuck Egypt)

Hi. I'm looking for a real man who can share his big dick with me. The bigger the better, boys. Black, white, latino, it doesn't matter to me. But be tall, fit, and between 18-35. I've never been with a straight man before, so I'm kind of nervous. I recently started hormones, so I don't have tits yet. Be clean and DDF as I am. You host or get a hotel. I'll give you the best head of your life and I absolutely love to rub a man's muscular back. If you're into rimming and being rimmed that can be arranged. It really gets me going to be on all fours while you fuck me doggy style. Would prefer this to become ongoing, but if the chemistry isn't there a one time thing works just as well. No married guys, or guys with girlfriends. I just don't want the drama! Hit me up with stats and a pic.

I love Craigslist. It is an all you can eat buffet of sex. Whatever I'm in the mood for is a click or a quick ad post away. I've always had a thing for trannies and I love doggy style. Their girly cockettes bouncing about as you slam into their ass. How nice and tight the anal cavity feels. This reminds me of a joke between a gay friend and a straight friend. The gay friend was remarking how he couldn't imagine having sex with a vagina and then proceeded to ask the straight friend what it was like. The straight friend replied, "It's like fucking the ass, but warmer, wetter, and looser." The gay friend seemed appalled. Personally, I like it all. This cross dresser was getting me all worked up.

Hi. I'm 5'7, 175lbs, and 7". I know you want someone tall, but my dick is certainly big enough to fill your girly holes. My back is muscular and so tense right now. I've included a picture, wouldn't you like to rub that? I'm single and can host, but I have a roommate. He wouldn't join us, but there may or may not be someone else in the apartment. Let me know and we can get this show on the road.

It's been three hours. What the fuck gmail? Where is the response?

Hey! I e-mailed you and haven't gotten a response. I find that personally rude. However, maybe you lacked the proper motivation. Here is what would have happened tonight if you'd responded to my e-mail.

You would have spent some time getting all put together and silky smooth for me. You come over and I feel you up under your clothes as we make out. You are one hundred percent smooth. If you hadn't been I'd have stripped those clothes off and forced you to the bathroom and shaved you smooth myself. Thank god it didn't come to that so that I may enjoy these soft beautiful lips of yours.

Your perfume smells nice. Floral, not overwhelming, is that a hint of blackberry? We begin to take our clothes off as we continue to make out. While in our underwear, yours looks gorgeous by the way, I begin kissing down your neck. You lift up momentarily to unclasp your bra. I continue to move along your shoulder then travel down to your nipples. I begin to suck on them for a moment, moans emanate from your full lips. They're more sensitive than you're used to, aren't they? I kiss down your sternum and move quickly along your stomach. I don't want to make you uncomfortable drawing attention to your six pack even though on you it is inexplicably feminine. I feel you tense up slightly as I lick your inner thigh and clasp a finger under your panties. I slowly draw them down to expose your modest penis. Before I can encircle it with my mouth you stop me. I was just trying to be a gentlemen and go down on you first, but you explain you aren't comfortable with that. I oblige. As I come up to resume making out with you, one hand cups your balls and the other grasps your chest to remind you that you can't pretend with me. I know who you are and I accept it. Your penis quivers and I let go.

Wrapping my arms around you, our arousal grows as our lips join together. I pull away and begin to turn you. I pull off my boxers and rub my cock along your welcoming hole. You inform me that you brought lube. I spit on my cock and on your ass. You like the feeling of degradation, don't you? I plunge in. In and out. In and out. In and out. I grunt approval of your boi twat and you scream appreciation of my big masculine dick filling your bowels. You shudder to think of the explosion of cum that will no doubt overflow from your being. I feel so deep inside of you that you imagine my cum will shoot out of your mouth and nose.

You're receptive like a real girl and that turns me on so much I don't know how much longer I can go. In and out. In and out. In and out. I'm thrashing in and out of you as hard and fast as I can. I tease you by reaching around a grasping your dick. You're so caught up in my onslaught of fuck that you almost don't notice. Before you say anything I release your girly member and allow it to continue swinging like a pendulum in time with our pleasure. In and out and in and out and in and out! I tell you I'm cumming and plunge in as deep and forcefully as I can. You scream your excitement. As I deposit my seed into you, you deposit your seed all over my floor. I pull out and tell you to lick up your mess. You look at me with tears of happiness in your eyes and tell me, "No, that's gross." We both break out into laughter and I ask you to come into my bed. You agree and we snuggle while watching netflix on my computer. Later that night I fuck you senseless again and in the morning you agree to come back again. But I guess you didn't want something like this, did you? Fuck you for not responding to my e-mail!

I woke up the next morning sexually frustrated. I was horny as fuck, but couldn't get it past half-mast. I knew what would work. I went to the kitchen and grabbed the can of whipped cream. I shook it. Up and down. Up and down. Up and down. I need this. I go to the bathroom, pull down my boxers, and bend over. The nozzle is pressed against my rectum. It slowly slips in. I love my tight ass. I'm ever so careful not to set it off just yet. I finally get it in and I press down. Whipped cream fills my ass and some even spurts out! Chills run up and down my spine from the coldness of the cream and the erotic thrill that tingles my rod. Not good enough. It barely moved. I know what I need. I need that fucking skank that didn't reply to my e-mail. Maybe she reconsidered. I better check. No. Nothing. Fuck this! Well, if she won't live out my fantasy, then I'll have to find someone who will.

I knew my friend Alex would be up for hanging out this morning. He comes over and we start talking about the erotic haunted house I was working in.

"Was that a real penis?"

"No, it is was dildo we drilled holes in and ran some pump through so it would gush blood. Yes, it is a real penis, just not mine. We picked them up from the morgue every night to use in the haunt."

"What?"

"Yeah, they're basically just sacks of blood."

"You're shitting me."

"Yeah. Glad you enjoyed the haunt though. Uh, hey."

"Hi?"

"Um, so, there has been something I've been wanting to try for a while."

"What is i-"

I leaned in and kissed my friend Alex square on the lips. This might be it, can't let it go. He tries to pull away, but not very forcefully. I hold on and he submits. He begins to kiss back. His mouth parts. His tongue tickles mine. Alex seems really engrossed in what he's doing. This will be perfect. I wonder what it is like to be so deeply exploring another person that time ceases to exist. I hope it is peaceful. I hope Alex will enjoy what I have to offer him. We pull each other closer. He is unsure of what to do. My cue. I never miss an entrance and I always pick up my cues. Delightful.

I reach into his shorts and begin to touch and squeeze his surprising manhood. I always thought he was super small. It isn't huge, but respectable, but then again I might have just had small expectations. He is beginning to moan and my hand is slick with his pre-cum. I keep my grasp on his cock.

"Alex. Your beard is scratchy. Could you maybe shave before we continue this? Please?"

The poor fool. He seems so flustered. I'm not even sure he realizes his best friend is jacking him off. He needs to get off so badly.

"There is a new razor and some shaving cream on the bathroom counter."

"Uh, ok, ok. Yeah."

I give him a few minutes to get started. I can't believe I've gotten this far. I wonder how far he'll let me take this? I don't really want to do this to my friend, but a man needs what a man needs. I enter the bathroom and come up behind him as he is shaving making sure he sees me in the mirror first so he doesn't get startled. Don't want any nicks on that pretty face. I look at him through the mirror. This might work. His face is definitely masculine, but has feminine traits we can accentuate. Really, with some make-up, the only thing that would be decidedly male would be his forehead. I've seen genetic girls with big manly foreheads. I can live with that. I kiss the back of his neck. I refrain from using teeth. I don't want to scare him off. Wolf in sheep's clothing is the best play at the moment. I'm glad he shaves without his shirt off. That saves me the hassle of getting if off. My hands reach around and play with his nipples briefly to subtly put the idea in his head. My idea in his head. I'm getting aroused at the idea of going through with this. He seems uncomfortable. Is it my penis at his back door? Is it my fingers on his nipples? Is it because I'm playing with him as he shaves. Oops, better be careful. I stop playing with his nipples and kiss the back of his neck again.

"Mm, don't cut yourself."

"I won't. I've done this before."

"With the mountain man style you've got you could have fooled me."

Keep this light. Keep this comfortable for her. Better watch it. Would hate to have slip of the tongue before he's ready. I reach around Alex and open a drawer to his side. I pull out another razor and grab the can of shaving cream from the counter. He is almost done with his neck and face. I put some cream in my hands.

"What are you doing?"

I begin to lather his legs.

"I know you were a swimmer. You talk about it constantly. Don't pretend this is weird for you."

"Well it is weird for my friends to be shaving me after playing with my cock. I don't think I'm okay with this. I'm not gay. I, I think I should go."

Think quick! He thinks he's straight. What would a girl do? I draw the razor down the lathered part of his leg.

"What the fuck? You know I hate pants, now I'll have to wear them until my hair grows back!"

"In for a penny, in for a pound."

"Fuck off, I'm not letting you do this."

Fuck! He must be mistaking me for the submissive one. It is kind of cute she wants to be in charge. She's already letting me do this. Well, as I said, in for a penny, in for a pound. Let's see what happens when I go for it. I pull down his shorts. His briefs are pulled down with them. Shorts, almost as good as skirts for easy access. Before he can react I take his cock in my mouth. About five and a half, wait, no, six. Yes, sex inches. Not thick, but big enough for sucking. Like a popsicle. I smile and coo as I look up at him with his cock in my mouth. Straight my ass, his cock got rock hard the second my breath touched it. He enjoys this. Come on, Alex, don't be a faggot and just enjoy this. Let me have my fun, asshole. I keep smiling hungrily. I slurp and try to make as much noise as I can. I'm sure he likes that kind of thing. After a good five minutes of bobbing about on his cock he begins to breath heavily. I deep throat the thing, or at least as deep of a deep throatting as I can with his cockette. I swallow gently and begin to pull out while applying just enough suction so an audible plop can be heard as I release his prick.

"Ooo, don't stop. So. Close."

"Then let me have my fun so you can have yours."

I begin to shave his legs. Slowly. Agonizingly. She begins to reach for her engorged clit. I pinch his taint and don't let go. He stops and looks at me. I move my hand around one of his balls.

"Do you want me to squeeze this like a stress ball?"

"No, no. No."

I lightly squeeze is balls, most people like this. I know from what he's told me about his sexcapades that he is particularly sensitive and hates it when people play with them. He is cringing and looks pained. What a pussy.

"Aw, poor baby. I know this is new for you, but trust me. This makes it better. Will you let me make things better?"

"Yeah, yeah."

"Yeah?"

"Yes. Yes!"

I release her pitiful ball. I finish shaving his legs. I lather his chest and stomach making sure I play with his nipples. He is a good boy as I finish. I can tell he is getting uncomfortable and losing interest in this sexual play. Maybe he really is straight. Then again, I've seen his porn. He doesn't realize all his friends know his kinks. I begin kissing him. I grasp his penis and he begins to take interest in this little make out session. I whisper in his ear.

"You've been a good boi. Let me finish what I've started and we can finish what we've started."

I'm glad he already had long hair. That will save money on wigs. He has very little hair on his back, so that goes quickly and I begin to rub some shaving cream on the crack of his ass. His body stiffens and his cock begins to deflate.

"Hey, everything else is smooth. At this point it would be just weird to not shave it."

The cheeks are smooth, which is nice, just the crack has hair. Not much, just enough to know you are fucking a man. I don't want to fuck a man. I wipe the cream away and Alex breathes a sigh of relief. He thinks we're done. I turn him around to face me still on my knees. His cock finds a home on my mouth as I lightly rub his balls. He moans and doesn't seem to hear the shaving cream being squirted into my hand. His balls are now covered in the white foam. I plop his cock out of my mouth again and rub some on his rock hard cock.

"We never did this in swimming! What are you doing?"

"Alex, you never shaved your ass crack in swimming either, did you? Don't be weird about this."

"I, I, but..."

Speechless, cute. I wonder how cute he'll be later tonight.

"Do you like hair in your mouth when you eat out a chick?"

"No."

"Well, I don't like hair in my mouth when I suck a guy off."

I mime pulling a hair out of my mouth. He totally bought it. But I really don't like hair in my mouth. He is now as smooth as I'm ever going to get him. He seems anxious, nervous, and horny as hell. He gives me a hungry look. Funny. He still thinks he is dominant. This will be fun. Still on my knees I begin jacking him off. He seems to like the new sensation of a hairless cock.

"Let me know when you think you'll cum."

"I think I'll cum!"

Wow, that didn't take long. I stop.

"Wh, wh, wh, uh, uh, why ah, ah, are"

"Shh. Think about baseball. I'm going to draw us a shower so you can get clean and then we can have some fun. You're not the only one who wants to get off."

I start the shower. I think about making it cold. No, I've got something I want to try. If this works, Alex will be a little cock-sucker and will never be able to deny it to himself. He will crave cock, cum, and me. His breathing appears to be under control. He is so close to cumming though. He gets into the shower first. I can already feel the warm steam on my skin as I undress.

"Uh, uh, ooo, uh, uh, ooo, ooo."

Grunts and moans filled with shame. Wonderful. I'm almost giddy with how well this is going. I quickly get in as he appears to be regaining his balance. He is slowly letting go of the sides of the shower. I slap his ass hard.

"Tell me what you just did!"

He tries to turn around and I slap his ass again and again.

"Ow! Stop!"

I don't.

"Tell me what you just did!"

I keep slapping him. I have to keep going until his anger subsides. If I give him the chance to hit me back this will have been for naught.

"Asshole, that hurts!"

What will it take? I begin hitting him harder until his legs begin to wobble. So close. I put my all into the next slap. Please let that work. I stop for a moment, unable to strike Alex again. I take a breath. Alex has curled up on the shower floor. He is crying from the pain and probably from the fact his best friend just beat his ass mercilessly. I really do feel bad about that, but he made me do it.

"Alex."

I lean in and give him a kiss.

"Alex. Can you please tell me what you just did?"

A little honey after the vinegar helps soothe the sting.

"I, I, I"

He is bawling so hard he can't speak. I give him another kiss tell him to take big boy breaths. When he has some composure he looks at me with big puppy dog eyes. She is so adorable.

"What did you just do?"

"I, I, it...it was an accident."

"Alex, what was an accident?"

"The water."

"The water was an accident, Alex?"

"The water it was warm and I was so close. It made me cum."

"Alex, I don't like liars."

What am I doing? I had him! Am I really going to take this further? Shit, he is going to regain his bearings and never let me go through with this. Hell, I probably just threw away our friendship forever.

"I'm not lying. I didn't touch myself or anything. It was the water."

Wow, his eyes are huge. He is bat-shit scared right now. Okay, I've got to maintain.

"Alex, you are in control of your cumming. You allowed yourself to cum. I am so disappointed in you."

Keep him off balance. I feel this is absurd. There is no way he is going to fall for this. I've got to keep this moving. I give him a kiss.

"Alex, it is okay."

"Re, really?"

"No. I'm still disappointed in you. I feel as though we were beginning to explore something real and you were selfish. I'm really hurt by your selfishness."

He looks moved to tears. How bad did that beating fuck him up? Are there issues I didn't know about?

"I'm sorry."

He begins to hug me and is sobbing.

"I know you are. That is why it is okay. Come on, let's get you cleaned up. You'd like that, wouldn't you?"

"Yes."

"Good because we're starting to prune."

He smiles a little. What a beautiful smile. I'm glad his lips are full. Well, full for a guy. They might be passable. I kiss him and stand him up. He is still crying a little. I get some coconut body wash and lather it all over his body. I take time to pay close attention to his nipples. He seems very receptive right now. That is good. When I get down to his ass I rub some between the crack. He doesn't seem to give off a signal as to whether he likes it or not. I don't press my luck. This is good. I grab some towels and start to dry Alex and then myself. I wrap a towel around his body as a woman would. Is he picking up the subversive nature of this yet? This may have been too obtuse. He is so out of it. I think he just wants to lay down. We've crossed so many lines in this last hour or so I think his brain is still trying to catch up. Well, in for a penny, in for a pound.

"Alex, your long hair. It'll drip and get everything wet. Here, let me help you."

I wrap another towel around his head and hair just like every woman seems to know how to do from the day they are born. It is so simple I'm ashamed at how long it took me to learn. I lead us out of the bathroom and make our way to the bedroom. I begin kissing him on the back of the neck.

"Doesn't it feel good to be smooth?"

"I guess."

"I think you feel good smooth."

I kiss his neck again.

"Can, can you rub my back?"

"Yeah, I can rub your back. I would love to rub your back."

I walk ahead of Alex and take his hand. It is smaller than I remember, but it isn't like we ever held hands before now. His hands are small and fingers are slim. If they were slightly longer he'd have the perfect hands for a pianist. I wonder how strong they are. I find the pressure point between the thumb and index finger. Hard as a rock. He is tense. I massage it slightly as we enter the bedroom. I am facing him and fall backward on the bed pulling him on top of me.