Friday, January 11, 2008


She was home from her first semester of college. She wrote to say that she liked my blog, and apologized for bothering me to write to say so. She stayed up nights to read it, she told me. She was eighteen and she had had sex a few times, but there were so many things she wanted to know about, so many things she had not done.

We traded notes. She wanted me to tell her what to do. I gave her simple instructions. She followed them diligently.

She had never had sex in a motel. It had been a while for me.

This is her account of our first date.

“Oh, boy, we even get to stay on the second floor!” I remark, as we walk up the stairs.

“We do . . . it’s a good thing, too; I don’t think we have any neighbors,” he replies, turning the key, opening the door to our room.

Once we step into the room, I put my bag down on the chair next to the door, and it’s clear that he’s already been in the room before picking me up. There is a bottle of bourbon on a table next to the ice bucket. Condoms and lube are ready on the nightstand tables.

I am anxious as hell, and he knows it. We kick off our shoes. He cups my chin in his hand, kissing me, parting my lips with his tongue. I pull back, and wrap my arms around him. He holds me.

“Such a brave girl,” he whispers, kissing the top of my head, running his fingers through my hair.

I step back from him, unzip my jacket, and take off my scarf. He sits on the bed and looks at me expectantly: our rule is that when we are alone together, I must be nude. I take off my clothes and lay them on the chair where I had placed my bag just moments before. He is standing right next to me. He holds my hands down by my side and orders me to stay still. I don’t say a word, He knows that I want to obey him.

“Close your eyes. And keep them closed.”

He begins at the top and moves down; stroking my hair, kissing the top of my head, my neck, shoulders, running his hands down my body, taking my nipples in his mouth, so gently. I sense him kneeling down, hands on my waist, running them down my legs, parting them, kissing the inside of my thighs and my pussy. He stands up abruptly.

“Honey, you are about to give the longest blowjob of your life.”

I open my eyes, looking up at him.

“Keep them closed,” he reminds me.

He pulls one of the chairs away from the table, throws a pillow down on the floor in front of it, guides me to it, and instructs me to kneel.

I get down on my knees, patiently, unable to see what he is doing. I trust him. I hear him open the bottle of bourbon and pour it into one of the plastic hotel cups. He pulls off his shirt, unbuckles his belt and unzips his jeans; I can hear him taking them off. Socks next. Then he sits.

He guides his dick to my mouth.

“You can open your eyes.”

I take it in my mouth, circling the tip, running my tongue underneath on that sensitive spot, one that I didn’t even know existed until he told me. I am nervous; all I want is to please him.

“Have you sucked a lot of cock? Hmm? Or are you just working on intuition?” he asks, sipping his drink, smiling down at me.

I sit back on my heels, look up at him and tell him that really, I haven’t sucked that much dick. I look back down, close my eyes, and take him deep in my throat. He groans, pushes my head down, urging me to keep going. I come up for air and ask him how I can stop gagging so much. I am glad that I can ask him questions and not feel foolish, He doesn’t mind answering.

“It’s good, you’re good, and you’re doing good. Jersey girls give the best head. There must be something in the water!” he laughs.

I suck cock for a while longer until he finally utters the words I’ve been waiting for.

“Get on the bed. I’m going to fuck you.”

I jump on the bed and lay on my back. He kneels in front of me, rolls a condom over his hard cock, and enters me, wrapping my legs around his waist. After a few minutes, he pulls my legs up over his shoulders. He held my hands up over my head. I fought back, although I loved every second of it. He made a comment about how he should have brought the ropes. I had already told him how I wanted to be tied up. After a while, he let up, and I moved my right hand down my body, resting it near my pussy.

“Go ahead. You can touch yourself.”

I start to finger my clit, faster and faster, to match his thrusts. I cum—my first time ever during sex. He knows this, and he slows, not pulling his cock out of me. He wraps his arms around my legs, which are still on his shoulders.

He leans down and kisses me.

“Um, was that an orgasm? Did you just cum during sex?” He smiles, and pretends to gasp. I just smile up at him.

He pulls me around and slides me up the bed, my head on the pillows.

He puts my legs back up over his shoulders and enters me again. I groan and throw my head back, bumping into the headboard. I start to rub my clit again—and he pulls out. He starts kissing and rubbing the inside of my thighs. I have my eyes closed, but I know he is watching me touch myself. I make myself cum again. And then, I feel his fingers enter me.

His fingers fill me up, hitting all the right spots. I moan as his mouth latches onto my clit, using his tongue; he is using both hands inside of me, alternating in and out, and he keeps hitting my g-spot. I am not so sure I have ever felt that before. Leave it to him. I have my hands up over my head, palms up against the headboard, eyes closed, breathing heavily. He makes me cum a few more times, and then I pull away.

“Why did you stop me? I was watching you before. I could see you have a sweet spot . . . and I went after it. We found your sweet spot, and your g-spot. You looked pretty damned hot.”

Then he laughs and demonstrated what I looked like just then.

We lounge on the bed for a while, and he holds me. His stomach gurgles. I mention to him how it is so college of him to be drinking out of a plastic cup. We start talking about my cocksucking. I insist that I really am nothing that special. He disagrees.

“Speaking of . . . you should probably get on that.” He points at me, then at his dick. “You know, you are the only cocksucker here. Beside me, I mean, and I can’t suck that cock.”

I decline and cross my arms. I make my “face” at him, and snap my teeth, pretending to bite. I am lying on my stomach next to him, and he spanks me, hard. I yelp. He continues with little taps, getting harder and harder.

He says he likes my ass. I laugh and tell him that he likes it more than he likes me.

He rolls over so he is on his stomach. He smiles and wiggles his ass at me.

“Spank me.”

I decline.

“You’ll be sorry. In ten years you are going to ask yourself, ‘Why didn’t I spank Jefferson when I had the chance?’ You’ll beg me, and I’ll say no.”

I laugh at him. He rolls over and gets back into his previous position, sitting, leaning back against the headboard, his legs sprawled in front of him.

I keep protesting that I really am no good at sucking dick, and he challenges me.

“You are. But if you don’t think you are, you should know that practice makes perfect. Now get going.”

I lay between his legs, taking his cock in my mouth once again. I keep gagging. I am embarrassed, but he thinks its hot, because to him, that means that he knows that blowing him is my number one priority at that moment. He knows I’ll do anything to please him. But it’s not really the best position to be sucking dick in.

He moves back to his chair, and I resume my place on the floor. My feet are falling asleep, and I will later realize that I am receiving my first rug burn. I can take him deeper in my throat now. He is groaning, one hand on my back, the other on my head, pushing me.

He tells me to get back on the bed, on my knees. I oblige, and he walks to the other side of the bed. I face him, but he tells me to turn around, smiling and gesturing with his hand. He rolls on a condom. He pushes me down and enters me again, this time from behind. He pushes down on my back; my face is squished into the comforter. He grabs my arms and pulls them behind my back; he holds them there while he fucks me.

He pulls out, and I move to lie on the bed, head on the pillows. He pulls off the condom, climbs onto the bed, straddles my chest and starts to fuck my face. I take him as deep as I can; trying as best I can . . . this is new to me. He comes so close, but he isn’t cumming.

I joke and tell him that I have failed him. He reassures me that it’s fine, and that we should sleep for a while. There is plenty of time for him to cum. I nestle into him, I like that I fit so nicely next to his body. He likes that I am affectionate. He kisses me.

A few hours later, we wake—the first time. He kisses up and down my back, and then turns me over and kisses me. We don’t speak. He flips me over, rolls on another condom and enters me from behind. He puts a pillow up against my headboard so my head doesn’t go through so much abuse. He fucks me hard, I touch myself, and I cum again.

He flips me over so I am on my back, and continues to slam into me. My legs are on either side of his waist, I reach my hands around and grab onto his ass, making him thrust harder. I grind against his flesh, bringing myself so close, but this time, I don’t cum. He does, and I couldn’t be happier. His body shakes, his eyes closed, his head back. He smiles and comes down to kiss me. I bite his lower lip. I am so glad he finally came.

We fall back asleep in each other’s arms.

I wake up a few hours later, and kiss his cheek. No response. He is fast asleep. I lie there next to him, and wait for him to wake from his deep sleep.

Around ten-thirty, he finally wakes, and tells me we have a half hour. We have to be out of the room by eleven. He puts his arms around me and suggests that we shower. I shrug, and he says we can stay in bed. He kisses my cheek, my eyes, and my mouth. He runs his hand across my chest, pinching my right nipple as hard as he can until I gasp and he lets go. He moves his hand down my stomach, and touches my pussy.

My eyes are closed, head turned to the side. He reaches to the nightstand to get a condom; I can hear the package ripping. I move, and look into his eyes. We can fuck once more before we have to leave. He puts my legs back up over his shoulders one last time and enters me. He fucks me slow, soft. I want more. I reach my arms around and grab his ass, pulling him into me. He gives me his fingers in my mouth, and I bite them and keep quiet, breathing heavily. He moves my legs down from his shoulders, holds them down. Our time together is running short. He pulls out, lies on top of me and kisses me.

“Really? We have to get dressed!”

I smile, and tell him I am not allowed, since we are still alone together, longing for more time with him. He tells me that it is time to go back to the real world. I complain that I hate goodbyes. He reminds me that this is only the beginning, and that the next time we see one another, it will be at his place. I smile; he pushes me back on the bed, straddles me, and kisses me one last time before we leave.


Anonymous said...

“You’ll be sorry. In ten years you are going to ask yourself, ‘Why didn’t I spank Jefferson when I had the chance?’ You’ll beg me, and I’ll say no.”


Eden said...

You know, I had a few choice words for this '?' person. Who hides behind a question mark anyway? But I chose not to say them, because I like to think of myself as a Good Person.

But I will say this, if Jefferson were truly lecherous, as you say, then he would not enjoy as many relationships as he does. Relationships that have spanned months, even years in some cases.

For alot of us there are reasons that go way beyond sex. We are adults capable of making our own decisions; no one is forcing us to sleep with him or spend time with him. We enjoy his company both in bed and out, and who is anyone to judge him? Because if you judge him then you should judge us too!

And if you are so offended by our ages, then why read his blog? Why not go find something more to your taste?

Damn, I'm all upset now, to quote Tess, 'I should go blog about this instead of writing a comment!' Plus I think I started half quoting something thats already been written up there.

desire said...

in agreement with avah and eden. if you can't deal with younger women enjoying the company of an older man, and said man enjoying the attentions of far more younger women than you will ever see, then i'd suggest crawling back into the hole you came from. jefferson isn't the evil letch you make him out to be, and you shouldn't read blogs that make you jealous.

desire said...

@avah: that's fair. i think your opinion is far more nuanced than either pro or con, and you've clearly thought about age and its implications in a sexual relationship. on the other hand, you're not on a moralistic bent against fragile, naive young women sharing themselves with sinister marquis de sade-esque perverts. sorry if you felt as though i put words in your mouth.

Anonymous said...

I think perhaps the comment in question isn't attacking May/ December's as much as it's pointing out that this blog might as well be called "Adventures in my Mid-life Crisis"

As for the rest, the hardline of defense & outrage by those who are clearly friends and lovers, that all seems a little too Jim Jones and family to make light of.

Jefferson said...

Don't confuse your twentieth-century Messiahs, anonymous. Manson had a family. Jones had a full-fledged cult.

Me, all I've got is Kool-Aid in the pantry and the lingering regret that it's too late to fall in love with Sharon Tate.

Still, if I had to have a mid-life crisis, I couldn't have chosen a better one.

Tilda said...

Does the Kool-Aid have vodka in it? I'm still waiting for that giant spaceship you promised and my brand new Nikes never came. I got the sweatpants though. They make my ass look big.

Bianca said...

Well now you're just being kind of silly. You seem annoyed that many people think you only fuck younguns but here is yet another story about you and an 18 year old!

Where are all the 30+ women, dammit?