A Tale of Two Paramours

Thursday morning started much earlier than I had anticipated, but I was far from displeased by that occurrence. My lovely, voluptuous brunette friend-with-benefits woke me up a little after 5:00am and informed me, "I want to finish what we started last night."

The prior evening, when I had roused her after she dozed off during the movie, Jessika asked if she could stay the night, since she had drank more wine than she had intended. I readily agreed, and we moved from the living room back to my bedroom. After undressing each other - and I must say I thoroughly enjoyed unbuttoning my shirt that Jessika had been wearing - we climbed into my bed, both of us intending to finish off the night enjoying one another. However, after just a few minutes of kissing and groping, Jessika drifted off to sleep, and I soon followed.

Now fully awake and rested, I was quite eager for a morning session with the sexy brunette. I stroked her sleep-messed hair as she bent down and wrapped her lips around my partially firm penis, which became completely firm quite quickly. After several fantastic seconds of Jessika's lips and tongue on me, she straightened back up before rolling on top of me and straddling me. I could feel the soft hair of her neatly trimmed bush on my sensitive shaft.

Leaning forward, her large, firm breasts pressed against my chest, Jessika kissed again me, her tongue plunging into my mouth. While doing so, she lifted up her pelvis, reached between us, found my hard penis, and adjusted it so that it slid easily into her wetness when she lowered her groin back against mine. We moaned in unison once I was inside of her.

Putting her hands on either side of me, she pushed herself up so that she hovered over me. Slowly, she began rocking forward and backward, my erection buried inside of her. Since she was still close above me, her wondrous breasts hung low enough that, as she moved, her nipples brushed against my chest. I would have loved to play with those delectable, thick nipples, but instead I grabbed her hips and added my own strength to her rocking motion, speeding it up.

Jessika leaned down far enough to kiss me, and then she pushed up and arched her back. This put her inviting breasts right where I could lift my head up and reach them with my mouth, and so I started kissing and sucking her half-inch long nipples as they jiggled in front of me. Jessika's moans increased in volume and tempo, and her gray eyes smoldered under half-closed eyelids.

Without warning Jessika, I sat up, clenching her to me as I pushed her upright. The curvy brunette let out a gasp and then buried her face between my shoulder and neck. Suddenly, her grasp on me tightened, she shuddered, and I heard muffled squeaks. Just as I had hoped, by sitting up I had changed the angle of my erection inside of her and pushed her over the edge.

After a few moments, Jessika let go of me and I lay back down on my back. It was still fairly dark, but I could make out that she was staring at me, mouth open, sweat-dampened strands hair covering part of her pretty face.

"Fuck, Mark," she breathed. "I didn't expect that."

"You did not like it?" I asked, trying to maintain an innocent tone of voice.

"Fuck yes, I liked it," Jessika told me, a smile spreading across her face. "It was a surprise - I went from thinking it was going to happen pretty soon to it happening right now."

The sexy brunette took a deep breath, which made her breast rise nicely, and then sighed.

"God that felt good," she purred. "It's almost like I am still feeling it. Did you know that would happen?"

"I thought it was a possibility," I admitted. "I dated a woman in college who loved it when I would sit up when she was riding me. My ex-wife never liked it, so I had not thought about it for some time. But when you were over me, it came back to me, and I decided to give it a try."

"Fucking fantastic choice, Mark," she grinned. "But we still need to take care of you before I leave."

"Get on your hands and knees and I will fuck you from behind," I boldly told her, and as I did so, I noticed that my use of the profanity was starting to sound less foreign to my ears.

Jessika grinned, pulled up off of me, started to go to all fours beside me on the bed but then hesitated.

"Do you want me on the bed or the floor?" she asked.

For the first time that morning, a memory of Jessi intruded - I saw her on her hands and knees on the floor of her apartment, looking back at me with those arresting blue eyes, asking me to fuck her. I saw her perfect butt and my hands on her slender hips as I thrust inside her impossibly tight wetness.

I forced myself to push thoughts of Jessi out of my mind, and instead I focused on Jessika's lovely face, her gray eyes eager and questioning as she waited for my response.

"On the bed, Squeaker," I told her. The curvy brunette stuck her tongue out at me at the use of the nickname, but she still dropped down so she was on hands and knees beside me. I took a moment to appreciate the way her large breasts hung pendulant below her, then I knelt behind her sweetly rounded derriere.

Grabbing her luscious hips, I pushed the head of my penis against her still wet pussy and rubbed it up and down. Jessika moaned and pushed herself back against me. Knowing she was ready, I reached down with one hand and positioned myself before slowly entering her.

Jessika moaned, "Fuck, your cock feels good in my wet little pussy."

"Your warm, wet pussy feel good around my cock," I told her, just somewhat self-conscious at my own words.

"Fuck me, Mark," she begged. "Fuck me please..."

One hand still on her hip, I reached around her torso with my other hand and grabbed one of her breasts. Then, as I squeezed it, I started pumping in and out of her.

"Oh God yes!" Jessika exclaimed. "Maul my tits while you pound my cunt!"

While my body did as requested, picking up the force and the tempo of my thrusts into her while squeezing and twisting her breast, my mind was a taken aback just a bit by Jessika's upping the ante with respect to the dirty talk. But I did not have much time to think about it (or perhaps overthink it). The lovely brunette did not give me a chance.

"Fuck yes!" she yelped, before starting to moan, "yes, yes, fuck yes..."

Letting go of her hip, I leaned further forward, putting the weight of my upper body on her now shaking butt and back, and grabbed her other breast, squeezing it and twisting it as well.

The now sweat soaked brunette groaned and began thrusting back against me. Soon we were lost in a rhythm of Jessika thrusting back as I thrust forward, my groin slamming against her behind with such force that she and I both grunted with each impact.

I was right on the edge when Jessika slammed her butt back against me quite hard and dropped down to her forearms, which pulled her breasts free from my hands. She then buried her head in the bedding and shrieked. Her entire body shuddered, and I felt her pussy tighten around me. This did it for me, and I moved my hands back to her round hips and grabbed on as I shoved my shaft as far in as it would go and climaxed deep inside of her.

As I ejaculated, Jessika's body went rigid, and I heard a combination of muffled panting and squeaking from the bedding in which her face was buried. But even through the interfering material, I could tell her squeaks sounded louder and deeper than any I had heard before.

Spent and soaked in sweat, I pulled away from her and lay on my back on the bed beside her. Jessika stayed where she was a few seconds before slowly extending her legs until she was lying on her stomach. It took some time for our breathing to return to normal.

As we both calmed down, Jessika lifted her head, her damp hair again hanging in front of her flushed, pretty face, and looked over at me. A small smile played across her lips and lit her smokey gray eyes.

"That was...," she started, but she did not finish - she just shook her head and kept smiling at me.

"Fucking fantastic?" I suggested, echoing her words from earlier.

My former student sat up beside me, smiled wider and nodded.

"Yes," she agreed, "that is a good way..."

The lovely brunette's words trailed off, and I saw her eyes go wide in shock as she looked past me.

"Shit!" she yelled as she jumped over me and picked up my clock.

"It's almost 6:30!" she blurted out, as she frantically looked around the room.

"Jessika," I started to say as I sat up on the edge of the bed.

"I have to be at work by 8:00," she cut me off as she snatched up her underwear and shoes, which were on the top of my dresser.

"What was I thinking?" she groaned. "I only have my dress. What am I going to wear home?"

Standing up, I went to the dresser, reached past her, and pulled out a pair of sweatpants and a sweatshirt.

"These will be too big, but..." I started.

"They will get me home," she finished. "Thank you, Mark."

Jessika kissed me, then pulled on the sweats. After she pulled the sweatshirt down over her impressive bosom, I noticed that even under that too large shirt her breasts were still noticeable.

"I don't suppose you have a rubber band or something I could use on my hair?" she asked me as she hurried into the bathroom and looked at herself in the mirror.

Tearing myself away from thoughts of her chest, I answered, "Actually, I have a scrunchy somewhere." It took me a few seconds to dig it out of a dresser drawer and give it to her.

The sexy brunette looked at me quizzically, so I explained, "It must have been mixed in with some of my stuff when my wife and I separated, and I never did anything with it."

"Lucky for me," she said, giving me a quick smile before facing the mirror again and pulling her now frizzy hair back into a ponytail.

Jessika studied herself in the mirror a few more seconds, then took a deep breath and sighed.

"I look like a just fucked whore," she bemoaned, before sighing again. "Well, not much I can do. I gotta run home, shower and get ready."

"Sorry, Jessika," I told her as she left the bathroom, grabbed her stuff from the dresser, and strode to the living room, where she picked up her red dress from the floor. It looked amazingly small in her hands.

"I think that is everything," she said as she put on her high-heeled shoes.

In other circumstances, I might have pointed out that her shoes did not match the too large sweatpants and sweatshirt, but I decided against it. Jessika had a great sense of humor, but I thought I might be pushing it, given the circumstances. Breathless, the pretty brunette gave the living room a once over before deciding she had everything.

"Yeah, I think I have all my stuff," she confirmed as she pulled me in for a quick hug and planted an even quicker kiss on my lips. Then, she was out the door with only a brief wave. I watched her hurry to her car before I shut the door.

About an hour and a half later, after I had showered and dressed, I was just starting work on some new material for my spring semester classes when a text from Jessika pinged on my phone.

"Just a little late. Barely had time for VERY quick shower. Still have your stuff inside me. Nice but messy."

"Sorry, Jessika," I responded, chuckling a bit at myself because I still could be a little shocked by how open she was about such things.

"Not sorry," she replied. "Feels great! Reminds me I am well fucked little slut ;)"

"Okay," I texted, wondering what else I should say.

"Gotta go. Work. Text you later," she sent back.

"Have a good day!" I answered.

A little after noon, I took a break from working on class materials. I was reading some short stories I had heard about during the semester - I usually caught up on reading, both for pleasure and to find new topics for class, after the semester was over - when a text arrived. My first thought was that it would be from Jessika, but my gut took over for my mind and I knew it was from Jessi before I even looked at the screen.

"Dinner ok. wrk 2nite. TPM?" was the extent of her text.

"wrk 2nite" I thought I understood, but I had no idea what "TPM" meant. So, I texted her back, "What does TPM mean?"

"tomorrow pm," she replied.

"Oh. Tomorrow evening," I sent.

"Y" she responded.

"Okay. How about 7:00pm? I will pick you up," I wrote to her.

"Y" again was her only response.

"See you then, Jessi," I finished, not expecting a reply. It was pretty clear she was either busy or avoiding a lengthy conversation, or possibly both. Thus, I was surprised when she sent a text that contained just a small graphic of a pair of red lips.

I stared at the little red lips, trying to decipher their meaning. Was it a kiss? That did not seem all that likely, given what happened after our one kiss to date. Was it a reference to the picture she had sent me yesterday, of her naked, on her knees, mouth wide open? That seemed more likely, but I was not sure. Could it mean something else? Something of which I was not aware? Had the generational gap between the twenty-year-old blonde and me again reared its head?

I tried to put thoughts of the quirky but sexy young woman from my mind, but I was unable to successfully concentrate on reading, or anything else, for the rest of the afternoon. A little after 4:00pm, I gave up and turned on the TV, looking for something that could drag my thoughts away from the allure of the petite blonde temptress. This also failed, and the different possibilities, and ramifications thereof, of continuing encounters with Jessi filled my head.

As I waged an internal debate about the young woman, at times I would resolve to stick with my plan and tell her we needed to not see each other. At other times, I would decide to give in and let myself be swept away by my lust for her. And sometimes, I would begin to work out plans that would allow me to both help her and enjoy an uninhibited sexual relationship with her. But no matter how far down such paths my mind would wander, I always would come back to Jessika's warning, and that would push me back toward deciding that the only thing to do was stop my contact with Jessi.

Thursday evening, Jessika and I texted back and forth a bit about her day, and some about our morning activity, but she was tired and I was not great company, even via texting, so our conversation tapered off as the evening wore on. After eating a quick dinner, I went to be and tried to calm my mind. But sleep eluded me.

After a restless night, including at least one vivid, sexually-charged dream about Jessi, I spent the morning figuring out how to pass the time until I saw the petite blonde that evening. I had concluded somewhere around 3:00am that it did me no good to keep thinking and re-thinking what I would or should do about her. I knew all the options, and knew which one made sense. I decided I would have to stick with that and make Jessi understand that we could not again do what we had done earlier in the week. However, even coming to that conclusion had not led to untroubled sleep, and I was facing the same concerns again now that it was light.

At about 10:00am, with nine hours to go before picking up Jessi, I gave up on finding anything at my house to distract me and spent the rest of the morning and the afternoon at a couple of my favorite museums. Even so, I was not able to distract myself completely from my thoughts and concerns about my former student, but it did manage to help the time pass faster. It was just after 6:00pm when I arrived back home and realized that I only had time for a quick shower before I had to be at Jessi's apartment.

After the shower, I selected my clothes while brushing my teeth. Like I had done on Monday, I chose casual clothes, although this time I wore a dark blue button-down shirt with black jeans. I also pulled a black leather jacket I had not worn for years from the corner of my closet. As I looked at myself in the mirror, I was happy to find that the jacket fit - it would not have just a year earlier - but I also realized I was trying to look younger than I was.

"Why do you need to look younger to tell her you cannot see her?" my conscience asked me.

Not having a good answer for myself, I just ignored my doubts and wore the leather jacket I had not worn since before I had met my ex-wife.

***

I arrived at Jessi's apartment door almost ten minutes late. I was a bit angry with myself that I was late after spending the day trying to make time go faster. I was also a little bit concerned that I was perhaps too upset about being late considering I had decided, several times the night before and several more times during the day, that this dinner was not a date, but rather an ending.

Jessi opened the door at the first knock, and as with the first time I had been at her doorway, I stood and stared for a few heartbeats. However, the cause of my staring this time was not a gloriously naked Jessi - rather, it was a Jessi dressed very nicely in a conservatively cut, blue satin blouse, a black medium length skirt, and medium height black heels. Her blonde hair was styled in long, loose curls that framed her delicate face, which was adorned with just enough makeup to emphasize her intense blue eyes and pouty lips.

"Please come in, Mark," she said. "I just need to grab my coat and my purse."

I stepped in and shut the door, a little surprised both by her use of my first name and how different her clothes were from anything I had seen her wear before. A wave of unease swept over me. Jessi was clearly taking this dinner as seriously as I was, but for obviously different reasons. I felt my resolve start to waver.

As I watched her walk to her closest, I could not help but notice that her skirt clung nicely to her hips and butt without showing any panty lines, which made it difficult for me to look away. Taking a deep breath, I managed to avert my eyes from her small but shapely bottom, but I worried it was all too late - I could now feel my formerly wavering resolve start to crumble away.

Jessi pulled on a long, dark coat and walked back toward me, grabbing a purse off her bed on the way. As she approached me, her bright blue eyes locked on mine and she bit the corner of her lower lip. Sensing her tension, I smiled at her. She immediately grinned back at me, and, when she was next to me, she reached down and took my hand in hers.

"I have never really gone on a date before," Jessi confessed, just before she pushed herself up on her toes and kissed me as the last of my resolve turned to dust.

***

Jessi sat on her bed crying as I opened a bottle of water for her. To say our date had not gone well would have been an understatement for the ages.

While I had not expected Jessi to kiss me before we even left her apartment, it was her comment that she had not really been on date before that truly caught me off guard. I knew from our past conversation that sexual relationships were nothing new to the petite blonde, so I had just assumed she must have dated before. As we drove to the restaurant, I tried to ask her about it, but I kept fumbling my words. However, Jessi soon figured out what I was trying to ask.

"I just have never dated," she told me, blushing and looking down. "I always just kinda hooked up with people. I never went out to a movie or dinner on a date."

"Uh huh," was all I said.

"Well, I did go to dinner for prom, but it was not a date," Jessi continued. "The guy and I were fuck-buddies already, so it was just dinner. I have not gone to dinner with anyone else; I mean, where it was just the two of us."

"I see," I told her, although I was just starting to really understand.

When Jessi had texted "No d8ts", it was a statement of fact as much as the expression of a philosophy that I had thought it to be. I realized now that, for her, dating was likely as much an unknown as an intimate emotional relationship. Again, I had stumbled into one of the traps that lay hidden amongst Jessi's social anxiety issues.