Jesse's Date

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I wound up really being my stepson's date.
4k words
4.51
250.7k
118

Part 1 of the 2 part series

Updated 10/24/2022
Created 08/22/2010
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jack30341
jack30341
1,883 Followers

Last weekend, I went to visit Jesse at college. Jesse is my husband's son from my husband's previous marriage. Unfortunately, Jesse's father and I are divorcing after seven years of marriage. It's very amicable, and it's almost like there's less stress with everyone recognizing that his father and I are splitting up.

Jesse's father is very independent, just like Jesse actually. In hindsight, it was only a matter of time, I guess. Jesse's father loves me, but he's bored easily. He didn't like a routine domestic home life, choosing instead to travel and be as socially active as he could. My job doesn't let me just pick-up and go, so there turned out to be more and more separation between us.

Jesse was fifteen when I married his father, making him twenty-two now. I was thirty-four when I married his father, so it seemed a little weird to have suddenly had a teeneage son, but we have always gotten along well. Jesse is still really close to his mom, and I would have never thought of myself as a replacement for her. It was more like we were as much friends as anything else, and I always tried to have it so that he could talk to me about anything when he needed to.

It was this closeness that prompted my going to see him last weekend. I was to help him get his new apartment settled, and he was getting over his recent break-up with his girlfriend. As soon as they had gotten back to classes, she'd let him know she'd started back to dating her high school sweetheart. He was pretty let down.

I talked and talked to him, trying to be supportive. I reminded him how he'd thought about wanting to be more independent and more carefree his senior year in college anyway. This was working out I told him. He should enjoy himself.

I made it a point to be supportive for his confidence, too. Jesse is ruggedly handsome like his dad. His dad is tall and athletic at six feet, and about 210 pounds. Jesse is actually 6'2", and probably 190 pounds, working-out regularly including swimming. With as much working-out as he did, he also watched what he ate, keeping his body fat well-contained.

The week before I came over to his college I sressed this to him in a phone call with him. "Jesse, just play the field. You're a good-looking guy. You're in good shape. Remember that any of those girls would be lucky to have you."

"Are you serious?" He chuckled in a way I hadn't heard alot from him.

"Yeah, sure I am." I reassured him. "You're a good-looking man. Remember that."

"Thanks, Anne." His voice sounded a little lower and relaxed, and I took this as appreciation.

Here is where I should mention that I should have been smarter. I've taken good care of myself, and I'm well aware that he probably really paid attention to what I said. I'm 5'5", and I'm about 120 pounds, being in good shape myself. I probably have been described by some as a sort of trophy wife, with my blonde hair and blue eyes. I have chosen to take it that Jesse listened to me, not just as his stepmom, but as a woman with good standards and experience about her.

Friday rolled around, and I drove to his college town for my visit. He was in a cool apartment, and we spent Friday afternoon and part of the evening arranging things and getting him settled. I met his roommate who was very polite, and they made sure I was comfortable and had what I needed in the small guest room that I was staying in.

Friday night I went with Jesse to a local bar where there was sports on television and good music from a deejay. We had drinks and laughed, and I was really relaxing and having a good time.

It felt somewhat like I was back in college myself, drinking and hanging-out.

Jesse was completely at ease with me, which I was glad about. It could have been a little less relaxed because of my getting divorced from his father, but none of that ever came up. I was glad for that. I liked not having to think about it or even talk about it.

After several beers, I noticed Jesse's demeanor suddenly change. He noticed people from school come in that put him on his guard. When I asked him about it, he let me know that the group included his ex.

"Hey," I turned his face to mine to make sure he listened. "Don't even worry about it. Don't let it ruin your night, you know?"

He gave me a half-grin. "Yeah, you're right. Who cares, right?"

"Right!" I smiled at him. Between the beers and the music, I must've been in some kind of mood, because it struck me how handsome he looked right then.

"Hey, do me a favor though," he asked.

"Yeah? What's that?"

"If they come over, you're Anne a friend from home, and not my stepmom. Okay?"

I couldn't help a big grin at him. "Sure, okay."

A great dance song started, and Jesse grabbed me by the hand. Leading me to the dance floor, he said to me, "C'mon Anne from home, let's have fun." I loved that attitude. We danced and laughed at our little front we were putting on.

He now seemed to make more contact with me than before, I realized. He took my hand a couple of times. He put a hand to my back now and then. It was clear to me he was wanting to have the ex see we were together. I didn't flinch one bit, completely at ease with his small gestures.

We had danced to a couple of songs already, when a slow song came on. Without really thinking about it, I made my way to leave the dance floor. Jesse grabbed my hand, and in a quick moment I found myself being pulled back to the dance floor.

Jesse was looking in the direction of his ex, as he pulled me to him. He probably didn't mean to, but he brought me up close to him to where we were pressed together at the front, as we started our swaying to the music. It must have startled him some, because he immediately looked down to my face once we were dancing and I hadn't moved away.

"Thanks for being such a good sport and all," he said to me genuinely. He was looking at me, and it struck me that he wasn't putting his attention back to the others. His eyes stayed fixed on mine. With the closeness of us and his gaze, I felt myself swoon a little, much to my surprise.

"Sure, Jesse." I said back. "No problem at all."

We went back to dancing and his face was next to my ear, as he spoke again.

"You look really great tonight."

He probably couldn't tell it, but I blushed a little. "Thanks." I replied.

As the song was starting to wind down, I noticed he was slowing our dance to an end. As we started to part, I felt him bring his face to mine. I looked at him, and he surprised me with a kiss directly on my lips. Startled, I kept in mind that Jesse was trying to keep up our scene as friends. His kiss lingered a little before he pulled back, and I felt a warmth.

His face left mine, and I couldn't help but look up at him. The kiss had been sweet and tender. His face was looking back to mine, when I felt his hand cup my cheek. After a brief moment, he brought his lips back to my mouth. He kissed me fully, and at first I just froze. His lips moved against mine, and I felt almost dizzy. Instinctively, my lips felt him and they puckered, joined with his. Jesse's head tilted slightly and I felt his lips work mine open. Jesse went from a full kiss to a deep kiss, his tongue exploring my mouth as I sighed back into his.

I didn't move away from him, and against all better judgment I felt myself just reflexively suck on his tongue and lips. I became focused on just how soft his lips felt and how his tongue moved in my mouth.

As quickly as he had kissed me, it abruptly ended. Jesse took my hand and was leading me off the dance floor. I was glad because I was in a daze. The rational part of me was saying he was putting on a front for his ex to see. The woman in me was reeling from a passionate kiss from this much younger man. I held his hand as he moved us back to our table.

We got back to the table without anything being said, and the server came to us. Jesse asked to pay our check. I looked to him and excused myself to go to the restroom. He just smiled and nodded.

I spent extra time in the ladies' room, looking at my reflection in the mirror. I put on lipstick and I tried to ignore an excitement about me. I downplayed what had just happened as Jesse just acting convincingly. I decided I was not going to make any big deal about it.

Jesse and I were walking out of the bar, and he was again holding my hand as we left not far from them. I grasped his hand back. It felt weird to be seeming as his date, but that was just what it was.

We were quiet as we got in the car. Jesse looked to me before starting the car.

"Thanks again for being cool back there." He said it matter of factly.

"Oh yeah, sure." As matter of factly as he had been, I thought I spoke awkwardly. My words were saying no big deal, but my voice was shaky. He just grinned and we left.

He made small talk as we drove back to his apartment, but I probably seemed distant. Several thoughts ran through my head. I hadn't been kissed like that in a long time. Jesse was a good, sensual kisser, I had to admit. And, as much as I chastised myself for it, part of me worried what he was thinking of how I had reacted.

By the time we were back inside the apartment, I had figured out that I would get on to bed and let myself sort it all out before I drifted to sleep, or even better, I would sleep on it and figure it out in the morning.

I told Jesse good night, and I went the direction of the guest room.

"Want to have a night cap?" He asked me.

Over my shoulder, I smiled to him. "I better turn on in."

I had gotten ready for bed but had not turned off the lights, when a soft knock on the bedroom door came. I froze for a second. I had on a tee and panties, which was what I had planned on sleeping in. I went to the door and opened it, but stayed looking around from behind it.

Jesse was standing at the door, and I paused. I first looked up at his smiling face, but it was impossible not to then notice his bare chest and abdomen. There's no other way to say it, except to say he looked chiseled, with well-defined abs. Patches of dark hair were at his chest and where his stomach went to his jeans, but you couldn't really call him hairy. He was still wearing his jeans, but his bare large feet completed the scene. I immediately knew I must've just surveyed him from head to toe.

I anticipated Jesse was going to make some kind of small talk or say he was checking on me. He didn't say anything though. He didn't even try to.

He reached his right hand to my wrist, and gently took my hand from where I was holding the door.

"Were you coming to check on me?" I asked him meekly, sounding myself like the one trying for small talk.

He didn't answer me. He just held my look and led my wrist closer to him. It brought me around the door. I stepped to in front of him, and I immediately thought of how imposing he was standing over me. I was standing there, feeling very self-conscious. My white thin t-shirt had to have been revealing my erect nipples poking forward. I couldn't even think about my thin, white silk panties, just barely covered by my tee. I should not have been standing in front of him this way.

His right hand left my wrist, and he brought both hands to hold my face. I trembled as his face closed the distance.

"Jesse," I managed to say his name before his lips joined with mine. He kissed me fully like before, and I kissed back. I felt how soft his lips were on mine again, and I thought of how I could stop this before it went too far.

His mouth opened, parting mine to receive his tongue again. This time he started gently, but it was as if an urgency was there. His mouth, lips and tongue were covering mine and he passionately held me. My hands went around his shoulders, and I felt the smooth, warm bare skin of him. I found myself rubbing my hands back and forth over him, sensing his firm muscled flesh as he continued to kiss me deeply. I hadn't kissed like this in forever, I thought.

My mouth opened wider for his, and I felt his hand drift to my buttocks. I tensed, and he brought me firmly to press my front to his. At once, I felt off balance, but it didn't matter as he was literally holding me up to him. My chest flattened to his, and the tee did nothing to hide how my breasts were free underneath.

One hand squeezed at my ass, and the other sank into my hair and worked my head to where my mouth was where he wanted. My hands clutched to his shoulders, and one hand betrayed me by going into his hair. We moved frantically against each other.

In an instant, his face left mine. It was so abrupt and unexpected that my head just tilted back, my mouth agape. I felt my tee pulled up, and then his mouth was on my breast. His lips sucked my left nipple into his mouth, and I felt his tongue flick at me. My hand gripped his hair, and I felt myself react between my legs.

I heard myself panting, and I told myself not to let him take my panties off. As long as I kept my panties on, I was okay. I relied on this thought even as he sucked and licked at my nipple amd my will power ebbed. I knew I was very wet.

Jesse eased me to the bed, and it was like a flurry of things happened. The front door of the apartment was opened and closed, meaning the roommate was home. Jesse was up to close my bedroom door and back over me in a flash. He kissed me again, and at once I was reminded of how much bigger than me he was.

As he kissed me, I felt a free hand of his go to my panties. I broke our kiss, and I put my hand to his there. My message was silent but unmistakeable. I had stopped him.

We paused and we were both panting now. He stood up in front of me. I watched in amazement, and he undid his jeans. He unzipped them, while he looked directly at me. I looked to his eyes, but I looked right back to his jeans. His hands were tugging them down his legs, and I found myself surprised. I don't know what I expected in terms of underwear, but I didn't expect boxer-briefs.

I was mesmerized as I watched his underwear as he pulled the jeans on off. The white cotton hid nothing. A large bulge protruded forward, and I heard myself gasp. I stared openly at him, and he stood there in front of me.

His chest moved up and down as he caught his breath. I was laying in front of him and I didn't remember how I became propped on my elbows, looking at him there in front of me.

Movement slowed down greatly, as Jesse's hands now seemed to go very slowly. He hooked his thumbs into the waistband of the underwear, and he stopped. I looked up at his face, and I became acutely aware that he had stopped just to make me look up at him. It was his way of making us both aware of how I was watching him.

My eyes noticed movement again, and my attention went back to his crotch. The hands worked the underwear over his hips and down his legs. Black, closely curled pubic hair appeared at the base of him. The waistband worked down the shaft of him just as deliberately as the underwear was going down his legs.

I sighed uncontrollably as I watched the thick, engorged shaft of him reveal itself. Finally, the underwear came off him, and his manhood jutted forward free. He was erect, but with his size it wasn't tilted up. It was pointed toward me. His head was large and defined.

When I looked back to him, he was looking at me taking in my response. He moved back over me, and I was very aware of every place he touched me. His hand went into my hair, as he started back kissing me. My mouth was open to him, but it was like I was still frozen. He rested on an elbow, and I felt his free hand take my own.

I felt him bring my hand to between his legs, and I wrapped my hand where I could to his shaft. I grunted into Jesse's mouth where he was kissing me. More thoughts sped forth, and I felt myself dampen more.

This was Jesse, my stepson. I was still married to his father, after all. He was nude and on top of me. I had him in my hand. Worse yet, I quickly reminded myself it had been months since intercourse. Even worse, I admitted to myself that I had never made love to a man this well-endowed.

Jesse heard a cry come from me, and he stopped kissing me. He eased himself back and looked into my eyes. I trembled more, as I stared right back into his eyes. He kept looking at me, but he brought his hands to my panties. My shirt had ridden up, and he could have looked down to see my silk covered mound exposed.

Instead, he kept looking into my eyes. He watched my eyes squench and unsquench, as his fingers went inside the back of my panties. This was the part where I was to tell him no. This was my boundary line, where I could put a stop to an exciting but a crazy episode with my stepson.

Jesse saw the resigned look on my face as I felt him slide the panties downward. They swiftly came down my legs as Jesse wasted no time. I felt relieved when he didn't let his eyes leave mine, even though he could've looked down at my now nude sex before him. A small trimmed trail of brownish blonde pubic hair was exposed and open, and I let myself remember there'd only been one man in the past seven years who had seen me there. He positioned himself between my legs.

"Hey, hey," I said quickly as he got between my legs.

"Yeah?" He worriedly responded, probably wondering if I was going to finally stop him.

My arms went up and around on his shoulders, and my hands went to both sides of his face to hold him facing me.

"Um, it's been a long time okay?" I sounded almost like I was pleading.

He gave a quick nod. "Oh, yeah. Okay." Reassuringly, he dropped his mouth back to mine, and the sweet kiss was there.

My legs splayed obscenely open, and with a smoothness I didn't really like, Jesse brought his arms back behind my legs. His face came up from our kiss, and I kept holding his face to look at him and he at me.

Jesse had a hand disappear between us, and at the same time, he moved just a bit forward. His moving forward had the effect of bringing my legs higher. Suddenly, I was very aware of how my legs were pointed straight up and my butt was no longer resting on the bed. I felt ridiculously exposed. I couldn't believe I was about to cheat on my husband.

Jesse brought the head of himself through my lips, and I moaned to Jesse's face. He rubbed his head through my opening, and he was coating himself with my juices. He seemed to look closer into my eyes and I knew he was about to enter me.

His fist held himself, and he eased forard into me. Jesse's eyes kept on mine, but my mouth opened wide, as he pushed his thick cock straight into me.

I cried out. Waves of pleasure washed over me, and he lodged where my lips clung to him. I didn't care---couldn't care---about his roommate or anyone else who had heard me. Another cry came when he pulled just some and then slid further. The only thing I could compare it to was when I was first taken when I was seventeen.

Jesse waited briefly, and then started backward. This time I tried to tilt myself higher and felt myself relax into him as he plunged, parting me. His face still watched mine, but I knew I must've looked pained or stricken. I didn't say anything but I brought my hips up in an effort to accept him.

With that, Jesse started rocking back and forth in me, and it was like he was touching every nerve inside me. It was like he was overwhelming me. I heard myself emitting a low moaning sound that clearly others could hear. Jesse rocked at me and I did back to him.

When a steady pace was going, I sensed Jesse make one pull backward that was different. Then, when he came forward, he fucked much further than he had before and I felt a flash of pleasure and pain. I screamed out and orgasmed harder than I had ever done before. My legs stayed outward, and Jesse was now pounding into me.

I moved my hips to him, but I wasn't keeping up at all. Jesse was just fucking me hard on his own. He was making me take him how he wanted to take me. I felt his cock hard and full as it pistoned in and out of me. He was grunting himself, and I was completely open to him.

jack30341
jack30341
1,883 Followers
12