I can’t believe that jerk Henry. He’s the same old shit he was when we were kids.
Mom had to go down to Washington to NASA headquarters, so I ended up at loose ends staying home. I took her to the airport and promised to be careful, no drinking or drugs, and not throw a party (who’d come, Mom?) and generally act like a mature adult, which, to be fair, I am.
I just get back home and Henry calls and says he wants to come over to party. I told him no parties, but he could come over if he wanted. He hesitated a bit and agreed. It was nice to be having some company, to tell the truth. He tells me his mother is also on some business trip to Georgia and would be out of town for the next two days. I tell him, no problem, we can hang out, maybe order a pizza and watch the game. He offers to stop and pick up the pizza, and, of course, I say “ok”.
So he gets here and we eat the pizza and are watching the ballgame and everything is normal. We’re sitting in the living room, him on the couch, me in a chair and just talking like you do during the game when it is going pretty slow. All of a sudden he looks at me and asks, “Do you still want to suck my dick?”
I mean who asks a question like that, it’s like ‘have you stopped beating your wife’. I answered it though, “Jesus Henry, can’t you come up with something different to say?”
He looks at me. “I know you want to suck my dick, I want you to suck my dick, so what’s the problem?”
“You’re an asshole, Henry, that’s the first one.”
“But an asshole who has a dick you want to suck, right?”
“For God’s sake Henry, think of something else.”
“Ok, do you want me to fuck you in the ass?” He smirked.
“Henry, think of something besides sex, ok?”
“Remember when our moms dressed us up when we got suspended? You loved it. Do you still dress up, Dave?”
“Henry, that’s the same subject. Talk about something else.”
“I guess that’s a yes. Do you have a full wardrobe?”
“Something else, Henry, concentrate.”
“Let me see it.”
“Let’s choose an outfit for you to wear when you suck my dick the first time.”
“The first time? Do you think I’m going to suck it more than once?”
“Oh. I meant for that this would be the first time at all, period. But, you’re right, it would be more fun if you did it a bunch of times, and changed outfits every time, while we have the chance. Who knows when we’ll have this chance again?”
“For God’s sake, Henry, think of something else.”
“Show me your wardrobe so we can pick something out. Wouldn’t you like to get dressed up this evening?”
“What’s the matter, Henry, no girls tonight?”
“Nobody who wants to suck my dick as much as you do.”
“Get over yourself, ok. Watch the game.”
“Do you have a cheerleader outfit? You’d look cute in that watching the game and blowing me.”
“A fucking cheerleader outfit? Are you absolutely crazy, Henry?”
“Well, I don’t know. Show me your wardrobe and we’ll pick something out. I like high-heeled shoes and red nail polish. It’ll be fun.” He smirked again and raised his eyebrows up and down. I couldn’t believe him.
“What makes you think I have a bunch of women’s clothes anyway?”
“Shit, Dave, I know how much you loved wearing them when we were suspended. In fact, you loved it so much I figure you have plenty out here in the country. Come on, let’s get started, time’s a’wasting. You could have those lips around my cock and sucking it.”
“Henry, this isn’t working. First, you don’t know what you’re talking about. Second, you are such a prick, even if you were right about anything, this would just be some cheap little trick to play on me. You’re sick, get help.”
“Damn, Dave, I didn’t think you’d be this hard to get.”
“Henry, for God’s sake. Has anybody ever sucked your dick before? Think, now, there may be a reason for that.”
“That was unkind, Dave. To be absolutely honest, no one has sucked my dick before, and I thought you might be the first since you’ve always wanted to do it.”
“My God, Henry, how did we get on this subject?”
“I have a hard on, and I want you to put those lips around my cock. I’ve been thinking about it for a long time, especially since I found out your Mom was going out of town the same time as my Mom.”
“You have not, you asshole.”
“Yes, I have. In fact, as soon as I heard they were going to both be out of town at the same time, it gave me a stiffy, you know?”
“That’s funny, Henry, really funny.” I rolled my eyes.
“As you know, having a hard on, thinking about you sucking me and me fucking you and beating off is old hat. I want to try something new. I want you to actually suck me off, and, I want to fuck your brains out.”
“Henry, for God’s sake think about something else.”
“I can’t. All I can think about is you wearing high heels and a short skirt and all made up and getting down between my legs and taking my boner in your mouth and swallowing my cum. Have you ever given a blow job?”
“Of course not, Henry. Who would I give a blowjob to?”
“Me. Here’s your chance.”
“Come on, then I can fuck you in the ass while you’re wearing your clothes, and you can put on another outfit and do me again. We can have fun the next two days. Two days, Dave. We might not have this opportunity again for years.”
“Henry, let’s look at this logically, ok? No.”
“Since you want to give me a blowjob and I want one, that isn’t logical.”
“Ok, how about this. Assuming everything you say is right, how in the world could you ever convince me it wasn’t just a trick? That will be a good intellectual exercise for you. Huh? How’s that for logic?”
“Not bad. I don’t know. What would convince you?”
This whole conversation was out of hand, totally. In any case, I couldn’t think of a thing. Henry and I had such a history. I remained silent.
“How about I write out in a letter that we mail to you in my own hand, that I came over here tonight to get a blowjob from you. We could take it down to the post office, drop it into the slot, and, presto, you’d be covered if I reneged on you.”
I decided to call his bluff. I got up and got a pen, paper and an envelope. I rummaged around and found a stamp and I wrote our mailing address on the envelope and handed the paper to Henry. “Ok, I’ll call your bluff, do it, and then give it back to me, I’ll put it in the envelope, seal it and we’ll drive down to the post office.”
Henry wrote on the paper, ‘To whom it may concern: I came over tonight to Dave’s house to try and talk him into giving me a blowjob, because I had a hard on thinking about him doing that. I also want to fuck him. I’m hoping he wears a real cute outfit and makeup. Sincerely, Henry’, and handed the letter to me.
I was taken aback. I didn’t expect this. I looked at the letter and looked at him. “Ok Henry, we’ll take this farce through to the end.” I took the letter, folded it, put it in the envelope and sealed it. “Come on, you drive us to the post office.”
I kept saying he was going to turn around on the way to the post office, but he didn’t. The trip back to the house was quiet. The letter was in the hands of the U.S. government. Henry finally broke the silence with, “I want to watch you get dressed and put your makeup on, me and you both knowing that you are doing it just so I’ll enjoy the blowjob more.”
I was quiet for a second. “Henry.” I paused, “For Christ sake, why?”
“I think you’ll look cute doing it. It’ll set the mood.”
I just shook my head. In any case, I couldn’t think of a way out of it at this point. When we got home, I took Henry to my room and showed him my wardrobe. He picked out everything, short skirt, blouse, high heels, bracelets, earrings, ribbons for my hair, every fucking thing. I was as nervous as I’ve ever been, with him watching me.
“God, this is going to be the greatest blowjob ever.”
“Henry, it’s going to be my first, it probably isn’t going to be that good.” I kept putting on my eye makeup.
“Yes, it is. You are going to look real cute with my dick in your mouth. I’m just hoping I can wait until you get your lips around it before I cum.”
I laughed. I wanted to say it, so just did, “Me too, Henry, me too.” I went back to putting on my makeup.
It took a while, but I finished. I couldn’t believe I was doing it. I turned around and smiled at him. “Well, where, Henry, where.”
He smiled back, “Right here, right now, on your knees.”
I put my hands on my hips and looked at him and, Lord help me, got on my knees. He surprised me when he grabbed my face and leaned down and kissed me. His tongue pushed into my throat. When that happened, I knew the asshole was sincere. He was sincere about the whole damned thing. He not only had plans to cum in my mouth, he evidently had thought about it for a long time. Go figure.
I finished the kiss, opened his fly and his dick sprang up. It was not the biggest. I think mine was bigger, but I wasn’t going to suck mine. I put my lips on the head and he gently pushed it into my mouth. The feel of Henry’s cock in my mouth was awesome. I tried to make it last, but the poor fucking baby was so horny. He came and came after a minute or so. I didn’t catch hardly any of it in my mouth. He surprised me. In fact, the force of the semen surprised me, and it took me a couple of seconds to get my mouth around it again. It was all over my face. The idiot kissed me again and said, “Time to change outfits.” And he got up and selected another skirt and blouse and jewelry combination and watched me get ready again. He’s a sick bastard. He lasted longer that time, though.
I don’t know how many blowjobs I gave him that night, to be honest. It took time between to hang up my clothes and get dressed in something else, but we did it far into the night. It seemed like he must have watched me put on my lipstick a dozen times, but he watched as carefully the last as he did the first. I do know for sure that dumb son of a bitch saw every pair of high heels I had in that one night. He kept telling me how cute I looked blowing him. God, how obvious can you be? I wanted to tell him I wasn’t falling for it over and over, that I knew what he was trying to do but not succeeding, but I guess actions speak louder than words.
I wore a cute baby doll to bed. The asshole woke me up and begged me for ‘just one more time’ during the middle of the night. We only spent four or five hours in bed, and we were up, and he picked out my first outfit for the day. It was funny, when you think about it.
True to the bozo’s fantasy, I gave him all the blowjobs he wanted and he still took my cherry and fucked me a couple of other times. I didn’t like it at first, but it grew on me, so to speak. He was like an ejaculation machine.
Every time I’ve blown him or fucked him since, I’ve made the idiot take me down to the post office and re-mail the letter. It’s got to be part of the ritual.
I want you to know I sure looked cute in all my different outfits. He loves them. I think my Mom knows, she doesn’t miss much, and that jackass Henry is suddenly around the house all the time. I’m not sure his mom does. He lives in their basement, there is a separate entrance to it, and she's at work all the time anyway. I keep the damned cheerleader costume over there. I absolutely refuse to wear high heels with it. I may not have my dignity or any self-control, so I guess I'm stuck with hanging on to what authenticity I can. Sigh.