Jesse's Date Ch. 01byjack30341©
During the night, I awoke panicky. I was mortified at what I had let happen. Gently and as sweetly as I could, I woke Jesse up and got him to go to his own room. I needed the space and time alone to sort through what had happened.
Luckily, his roommate was up and out the door early the next morning. It was awkward at first when I was around Jesse, but I just gently explained how wrong it'd been. He seemed to get it when I mentioned how very hurtful the news of this could be, if others learned. He went along with me, and he acted like he understood, which I was so very glad for. I asked him if we could still be close. I was so happily surprised when he looked both relieved and excited at the thought of it. He said that we could certainly still be friends. We hugged as friends and decided we'd just enjoy the day.
We laughed and talked easily. We ate brunch at one of his favorite places. We decided at brunch that we both needed a good work-out, so after brunch and some walking around we went back to his place and got our work-out stuff. He was such a cool work-out partner to let me just have my space and do what I wanted to do. We met back up after the work-out and a good shower.
Once we were back in the car, my cell phone started going off. Of course, it was my husband. Like some sixth sense, he had a knack for calling and getting my attention at the very times I probably didn't need it. I talked with him a good while, and I think Jesse and I both felt even more resolved about how wrong last night had been when I got off the phone.
"How was he doing?" Jesse asked, a distinct tone of concern in his voice.
"He was good. He asked about you."
"Geez. I feel like the worst guy ever."
"Well, don't beat yourself up, but now we know just how much of a mistake last night was. It has to stay our mistake. You know?"
"Yeah, yeah. No question. Did he say much else?"
I hesitated. I didn't want to make Jesse feel even worse. At the same time, I wanted to be honest with him. "Well, actually he did."
Jesse looked at me, and I gave a concerned look back.
"He said he's thinking of me. Says we need to take our time. Acts like he's re-thinking the whole 'break-up'."
Jesse sunk in the driver's seat and seemed to deflate. I wasn't trying to let him off the hook, but I did feel the need to be honest with him.
"Hey look," I explained, "he has phases like that. We do care about each other, no question. But... he's not wanting some monogamous home life. Believe me, he's just not."
Jesse looked at me again as if to wonder about where I was coming from myself.
"Um, just the same, we can't possibly have anything happen or anything said. We just can't." I was firm.
Jesse nodded. "Absolutely. I understand."
I believed him.
We hung out the rest of the day together. I had a great and relaxed time with him,and he seemed to with me as well. We did some shopping, and he showed me around some sights in the area.
Evening came and we hit a restaurant for drinks and dinner. We laughed and talked easily. I caught myself several times thinking about how much I enjoyed hanging-out with him. He was so charming. It was also relaxing because it wasn't like he started in on me about anything or tried to get me to reconsider what I'd said.
We were getting ready to leave the restaurant and one of the waitresses openly flirted with Jesse. It was cute in a way. Jesse seemed a litlle embarrassed by it, but I just chuckled. It was interesting seeing him adored like that. It reinforced my picture of how attractive and personable he was. I kidded him as we left, telling him he'd have to be sure to return sometime---without me. He just shook his head and laughed.
At home, we may have been just a bit awkward. He got quiet, and I didn't think we should tempt things by hanging out alone more. I got ready to call it a night.
"Listen, I want to thank you for being so understanding." I reached up to him and embraced him. He hugged me back and we didn't leave each other for a long moment. I have to admit it felt very good in his arms. His embrace was secure, and his body felt so solid. I didn't move for a while, even though I should have broken off sooner.
When we parted, I brought my face back to his and gave him a tender kiss on his lips. He looked longingly into my eyes as I moved away from him. I turned and went to my room, listening to him behind me as he went on into his own room.
I closed my bedroom door, and exhaled deeply. Leaning back against the bedroom door, I closed my eyes and let my thoughts run wild. His easy-going and accepting manner about the day and evening was so welcomed. It couldn't have been easy given the night before. Yet, he had been so very sweet and understanding with me.
Even more, there was no denying a connection between us. Last night had been passionate, but today had been fun and exciting, too. We'd talked easily. Laughed. I had to admit to myself it'd been fun hanging out with him.
There was more I had to admit though. I winced as I thought about how I'd been like an excited school girl much of the day. I liked his attention. I liked our kidding around. I especially liked the interest he showed in me. I also liked showing interest in him. There was no denying it. And, I even had to admit something to myself---what was that pang I felt when the waitress had flirted with him. That couldn't have been some jealousy, I told myself.
I started to the bed to start my ritual of getting ready for bed. My hands went to my hips as I got very torn about my feelings. The thought entered my mind of it being Saturday night and I was feeling restless. Hey, maybe I'd give myself some relief, I told myself. A smirk crept over my face. Maybe I'd replay parts of last night. I abruptly froze. I shook my head, slowly trying to deny the strong feelings I had to betray my better instinct. I noticed my chest lifting up and back with deep breaths.
A nervous excitement coarsed through me as I thought of Jesse who was just across the hall from me. Stop, I pleaded with myself. What was I thinking? My mind betrayed me by flashing reminders from my time with him. The feel of his skin on mine. The look in his eyes. The parts of his body.
I tried to make myself think of my husband. Tried to remember that I was the older and experienced one here. Still, the effortful thoughts seemed to dissolve. Rather, my mind imagined the short walk across the hall and what was possible. Then, my body followed. As if in a dream, I sensed my hands pat my hair, vainly straightening it. A fading thought said to lay on my bed and use my imagination.
Still as if in a dream, I let myself go back out of the bedroom and across to Jesse's bedroom door. My feet padded across the rug, and I felt scared at what I was doing. My hand reached up and knocked without any plan whatsoever.
"Yeah?" His surprised voice answered.
I opened the door and entered. He was sitting on the side of his bed and looking up at me with his mouth open. Clearly he was shocked to see me there. I stared back at him a moment.
I closed the door behind me, and I stood there just inside his bedroom. I felt giddy excitement but didn't know what to do next. I couldn't help but wonder if he could tell I was shaking. I put my hands behind my back and leaned against them and against the door.
He just smiled. He was probably disbelieving I'd come into his room like this.
His smile turned mischieveous.
I looked back at him intensely. I wasn't sure what I'd do next.
A few seconds passed as we looked at each other. A distant voice told me to leave, but I wasn't going anywhere.
I shook my head slowly. "I should not be here."
I could tell he was only in his boxers, but it was confirmed when he stood from the bed. He paused and kept looking at me. I sensed movement and my gaze went to his boxers. He was tenting his boxers with a growing erection, and I let myself watch the bulge fill his crotch. My eyes drifted back to his face, and he had a beaming smile at knowing I had stared. I grinned back reluctantly.
I braced myself as he started over to me. His hands cupped my face and he closed the distance to kiss me without my moving at all. Those soft lips I'd remembered from the previous night kissed me fully. I felt my lips part and his tongue slip between them. I licked at his tongue, but then pulled back. I brought my mouth off his, and I was looking at his mouth as I leaned back against the door and away from him.
Undeterred, he again closed the distance and kissed me fully, with the effect of pinning me to the door. I don't know know if it was a matter of me or him, but my lips parted wider and his tongue worked about inside my mouth passionately. I fully kissed him back.
Our faces and mouths moved together as we urgently tasted one another. My hands were rubbing his back, when he broke our embrace. He reached his hands under my blouse and pulled it up and over my head, and I found myself only in a bra and my jeans.
He knelt and began undoing and stripping my jeans and I told myself to make him stop. Instead, I put a pliant hand into his thick head of hair, and I watched his large hands unzip my jeans and start tugging at the sides. I felt open air at my crotch as the jeans were slipped down my legs. I softly moaned at the sight of him undressing me and the knowledge I should be stopping this though I wasn't.
His hand slung the removed jeans away, and I saw him peer at my panties before his face. Unexpectedly, he pushed his face into my crotch. I yelped at Jesse's mouth forming directly over my sex at my thin satin panties and he sucked at my scent and taste there. I felt I was probably dripping at this point. After quick moments of his face wedged to me there, he yanked my panties off my hips and to the floor. His mouth darted right back to me, and I inhaled sharply when I felt him cover my wetness.
His tongue stirred in me, and I shoved back at his shoulders unable to take it. As if in response, he stood. His hands grasped my sides and he pulled me up and against him. My legs wrapped against his hips, and I was very self-consciously aware of my bare crotch straddling his hardness still encased in boxers.
He brought us both backwards. Me up and craddled in his arms, and he backpedaling to the bed. When he got to the side of the bed, he sat down with me landing atop his lap. I raised to my knees where I was hovered over him as he stretched backwards and laid back. His hands had guided my back to where I was positioned over him, and then his hands made short work of the straps of my bra, releasing my breasts to spill down and jiggle shamelessly in front of his face.
He put a hand to one of my breasts and squeezed and my head tilted just back at his manipulation of me. As I felt the one hand massage my bare breast, I felt his other hand go between my legs. There was a quick respite where I didn't feel anything happen with his second hand and my eyes drifted back down to look at his face.
He held my look intensely, and he watched my eyes knowing I'd soon react. I felt his exposed hard cock being held out and up against my lips down there, and I tensed my brow and face into a look of realization of what was happening. He looked back at my face that had to look distressed, my mouth open and eyes half closed.
"OH, OH, OH," my high pitched voice could only manage as he rubbed his hard member against my lips and opening. "OHHHhhhhh." I cried looking into his eyes.
I felt defenseless on my hands and knees over him. My hands gripped into his sheets, and the smooth round head of him manipulated my wet helpless lips.
Tingling jolts shot through me as his circular movements with his head changed to an up and down tracing of my lips. I would realize later that he had been simply coating himself with my own juices on him, but at the time I just focused on the feel of him rubbing me there.
I widened my eyes back to his as I felt what he'd done. He'd wedged himself into my opening. What had seemed formidable with his size last night now seemed impossible, and my mouth opened as if to speak. Before words could form, his hands came around to grasp my hips and those hips lifted into me.
"AAAAHHHHHHHH!" I exclaimed as several inches plunged inside me. Pleasure and pain washed over me and I shook in a series of orgasms. "JESSE, JESSE!" I cried to him.
He kept looking at me, and he withdrew himself some. I thought he'd given me a reprieve to catch myself, but his hands pushed my hips again and he lifted his hips fully.
"OOOOOOHHHHHH!" I screamed out as his cock filled me and he pressed to the back of me. My back arched and I could feel my chest lift up and out. I was mounted on him fully. My hands squeezed at the sheets.
He pulled back just some, and I pleaded to him aloud. "JESSE, JESSE... ."
He thrust up again and I cried out again. Waves of pleasure came through me as I felt his cock plunging and rocking inside of me. "Wait, wait, wait." My words frantically cried to him and he grunted.
He started pumping at me, and for a second I thought I was passing out as I got dizzy. I was self-consciously being bounced on top of him by his thrusts. I had no control whatsoever as he used his hands to keep me in place and used his hips to pump long sure strokes through me.
My body felt tossed like a rag doll. I yelped at the sensation of his large cock pulling my lips outward only to plunge right back in me. When he drove deep inside me, I felt the walls of me stretch to give in to him. I cringed in another explosive climax and the dizziness almost loosened my grips from the sheets.
He incredibly kept pumping at me, fucking me with abandon despite how loud I had responded. "Jesse, Jesse, BABY," I tried to slow him. He writhed under me and kept drivivng, and then another thought hit me. One I had considered off and on throughout the day.
"DON"T!" I pleaded aloud. "DON"T you cum in me! Please don't cum in me, Jesse!"
I was looking down into his eyes, and when I finished my admonitions, it was like the thought hit him, too. His head tilted into the bed and back and his back arched with the effect of another deep thrust into me. Then, I felt it. His shaft and head pulsed and kicked, and against all my wishing against it, it was like my vagina just puleed and sucked as his semen shot into me.
He moaned very loudly. "AAAAAAHHHHHHHHH!!" He was grinding as if trying to stretch me more, and I succumbed to another numbing cum of my own. I pulsed and writhed sitting atop him and it was like tremors of pleasure kept shooting inside me, as how large and filling he was made me take notice.
I didn't move, but I did try to speak. "Oh, oh. Jesse, I... I dunno."
His eyes were almost shut but still peering at me. His cock was still buried in me, and I was glad neither of us went to move.
His voice was very low and concerned when he spoke. "Ummm, are you... are you okay?"
My intial inclination was to be reassuring and say yes. I just stayed silent a bit and took in the moment. I had never felt anything as intense and overwhelming in all my life. And here I stayed perched, not even moving from where my stepson still had his large cock stuffed inside of me. Worse, he had ejaculated into me. The longer I stayed straddling him was the more my pussy relaxed to clasp to him and stretch still for him. It was like my mental analysis couldn't catch up to my physical memories and sensations.
"Anne?" I focused back on Jesse's eyes, and they showed genuine concern. It occurred to me that I still hadn't responded to him. He twitched inside me, and I inexplicably felt as though I were emitting more wetness.
"Anne, say something. Are you okay?" His hand stroked at my back.
"Um, I don't know what to say. I'm okay. ...Yeah, I mean, I'm okay." My jumbled delivery of words made me wonder if I really was okay.
Jesse smiled and then hand that wasn't on my back stroked at my cheek and face. "That was incredible." He meant it.
I took deep breaths and tried to orient myself to my thoughts.
"Was I too rough?" He was asking me directly, and I paused.
"I, um, don't," I wasn't sure what I wanted to say. So, I stopped trying to guard myself. I said what I felt. "Jesse, I have just never felt anything like that. No one has ever... ."
I had started to say 'made love to me like that', but I stopped and restarted. I looked straight at him. "No one has ever fucked me like that." My directness immediately made him pulse and I blinked at the sensation of his reaction. He had a very serious look on his face.
There had been a relaxation of his shaft before. Once we'd stopped, it had seemed to ease, but I felt him move in me again and I absolutely could not believe he might be engorging again. We both stared at one another as the physical dynamic changed. I sensed his reaction was to my choice of words.
"Yeah?" He asked me almost tentatively.
"Yeah. I'm serious."
He gulped and took in my genuineness.
"Um, okay." His words seemed to be superficial, as if to buy himself some time.
I moved my hands from the sides of his head where they had gripped onto the sheets and I brought them to his bare chest. Uninhibitedly, he stared at my exposed breasts hanging downward. They hung heavily forward and I could feel my nipples still erect and protruding. His continued stare just soaked me more.
"Do you like them?" I blantantly asked him and he stared at my eyes looking like he had been caught and might need to apologize.
"Yeah. Yeah, I do." He admitted.
One of my hands left his chest, and I brought it to the hand that had been at my cheek. Without a word, I placed his hand to where he was cupping my full breast. I left it there and he massaged me. I winced when he clasped my nipple between his fingers, as electricity shot through me.
The physical connections between us and my overt reaction to his fingers to my nipple seemed to awaken him, and he jerked inside me. It left him feeling stiff deep in me again. We both gazed at one another in unspoken acknowledgement of his having gotten excited again. He'd never left me.
"Know what else?" I half whispered the question to him. I tried to tell if my question was as provocative to him as I had intended it.
I shifted on top of him, and I studied his reaction. He was trying to figure out whether I was getting more comfortable or starting to move away.
"There's something I like, too." I said it quietly. He looked up at me and he gave a small smirk as if to try to gauge where I was coming from.
"Yeah? What's that?" His voice was ragged, and I savored this momentary advantage I seemed to have over this twenty-two year old.
I gave a small smile and continued to move. I had shifted up at first, like I might pull up and off him. Now my hips just centered more over him. I hadn't moved away. I'd stayed over him. He inhaled sharply and with the exhale, the penis filling me got harder still. We both knew it.
"Well, there's something I like a lot, actually." I continued deliberately. He grinned and I sensed we both knew he was now vulnerable to me. I brought his second hand around me to join his first at my chest though I didn't have to place it on my other breast. He did that himself.
My hands rested back to his chest, and when his own hands gently squeezed both my breasts, I instinctively brought my hips forward in place. I didn't bring them much and I didn't bring them as if to release him. My nipples felt raw to his long fingers.
"Anne, what is it? What is it you like a lot?" He was as hard as before and we both could feel it.
"Well, don't know if I should say, really?"
"C'mon, sure you should."
My hips started small, slow movements that were just up and then just back. He flexed himself inside me, and we both looked in each other's eyes at the sensation.