Oh, Jen!! Ch. 09

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Thigh high boots and tight dress, oh my!!
7.1k words
4.7
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Part 9 of the 10 part series

Updated 06/09/2023
Created 08/30/2018
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I turned on The Weather Channel this morning around 9 to see Jen Carfagno and Alex Wallace sitting on the couch they now have on set for a more causal look. Jen was wearing a dark yellow dress and boots. They looked very tall, but I was about to get a jolt. Jen went over to the wall to do a segment on yet another winter storm that was sweeping across the plains. I watched her get up off the couch and move to a standing position.

HOLY CRAP!!!

Someday that girl is going to put me in cardiac arrest. As she stood, I could now get the full picture of Jen. She was wearing a short, tightly fitting dark yellow dress that came to about mid thigh-and thigh high black boots with a four inch heel. How she got off the couch without giving Alex and the rest of us a wide open crotch shot, I can't figure. Getting up in a short dress without flashing the place is one of those mysterious things girls learn early on that guys just can't figure out. I watched as she walked to the screen, mesmerized by the way she strode across the stage in the tall boots-and Jen walks in high heels like no one I've ever known.

At the screen, I watched her do a two minute segment on the approaching storm. I didn't see any of the storm report, but I did see a lot of Jen moving back and forth as she pointed to various parts of the map, her tits straining against the material of her dress, her ass seeming to get so close to peeking out as she leaned down to point to somewhere in Texas, and those long thighs, accentuated by the boots and the shortness of the dress. It was all I could do not to pull my dick out and have a nice fantasy fuck with Jen right there in the living room, imagining her pushed up against that big screen, her panties pulled down so they were hanging on the top of her boots, my dick buried in her pussy from behind, pumping her til I flooded her little dark haired pussy, then pulling out and watching my cum run out from under her dress and down her legs as she straightened up, turned to the camera and smiled.

I resisted the urge, knowing that some days Jen will stop over at my house for a late breakfast, or just for coffee, before she goes home next door. These encounters often result in a quick screw on my sofa, and occasionally, a longer, more leisurely love making session in my bed. Two hours later, I was glad I'd held off. I got a text from Jen:

"Hey, want to meet me for lunch??"

This was unusual. Typically, she'd just drop by my house when she got home, and I'd become accustomed to hearing her car pull up, then a few seconds later, the click of her heels across my deck, and her cheery voice greeting me as she came in my back door.

"Sure. Where are we going??"

A moment later came the reply.

"Meet me at Gondolier." Gondolier is an Italian restaurant/pizza joint in a strip mall in a northern Atlanta suburb.

"OK. In an hour or so??" I figured Jen would need time to get up from Atlanta to the restaurant.

"Yeah, be there around 1."

"Good deal. I'll have us a table. See you there." I added a smiley emoji, the smiley holding a knife and fork.

An hour later, Jen was just getting out of her car as I pulled up. She had parked a couple rows away from the building, and I got a good look at her in the dark yellow dress and thigh high black boots. The dress seemed tighter and shorter than it did when I was watching her on TV earlier this morning. Her C cup breasts were straining the fabric on the dress, and I wondered if a little breeze might not lift the hem of her dress, giving the world more Jen than they could ever have hoped for. She looked amazing, good enough to eat, and I told her so, to which she responded with a giggle.

We went inside, Jen walking just ahead of me. I enjoyed the view of Jen's thighs and ass as she walked, my cock rising as I contemplated what was under the dress. We took a table near the back. Jen sat as I hung our coats on the hook at the booth. When she hit the seat, her dress rode up as she started to slide in, and I got a short but just long enough glimpse of her shapely thighs and a sheer pair of black panties. They did little to hide her full bush, of which a few stray hairs were escaping the leg bands. I started to get hard imagining what was coming after lunch.

We had a pleasant lunch, Jen explaining that she had gotten a late start, then had to deal with traffic, and didn't have time to stop for anything before going on. It was vending machine food all morning, and she was really hungry, and wanted a good lunch. I couldn't fault here there, and it was nice to be on a sort of "date" with her after all this time. I'd have taken her anywhere, but this was close to home, but far enough away to not draw any attention from neighbors who happened to catch us-not that lunch in itself is a problem. It's what happens next. As anyone who is out in the world today knows, there are eyes everywhere, and even something as innocent as a couple of friendly neighbors having lunch turns up on Facebook. Jen, being as well known as she is, has a problem sometimes with being noticed in public. The place we picked is a little more private, as the strip mall it's in is only about half occupied, as it has lost its big stores, the largest now being a Dollar Tree at the other end of the building.

After lingering over tiramisu, we thought it might be time to move along. We left the restaurant, Jen again giving me a good flash of her thin panties as she got up from the booth. We walked outside to our cars. It was all I could do not to take her hand as we walked. We got to mine first, and Jen turned to me as I unlocked it.

"Follow me," she said, leaving me and heading to her car parked a couple rows behind me. I watched her dress flounce as she moved, striding as she does in high heels. It drew my attention to her thighs, which I was seeing a lot of from behind. She smiled as she got in her car and started it. I got in and started to follow. She drove over to a corner of the lot, away from the stores, and not really obvious to someone coming or going from the mall. I pulled up two spaces over from her. She jumped out of her car, and got in the back seat of mine, pulling the door shut as she slid in. Her dress was riding high as she sat with her legs parted, and I had a clear view of her sheer panties I had seen in the restaurant, and the treat that awaited me beneath.

"Well, come on back!!" She said, smiling. I cracked the front windows about three inches. It was a cool and cloudy day, maybe mid 50's. I hoped that would be enough to keep us from overheating. Nah-nothing was going to keep us from overheating!!

I moved to the back, sitting next to Jen. I turned to her, and she met me with a long, deep kiss. As we kissed, I rubbed her tits through her dress. I wanted to get my hands on them as I had so many times at my house, but it was a back zip dress, and really not conducive to easy access. Besides, the thought of taking Jen fully clothed was a turn on.

While we kissed, and I was feeling Jen up, she was doing the same, undoing a couple buttons on my shirt, running her hands through the hair on my chest. She pulled her hands off my chest and reached for my jeans, now rubbing my cock through the denim. I was already well on the way to an epic hard on when I sat next to Jen. Her hand moving up and down my now straining erection was getting me the rest of the way quite rapidly, something not lost on Jen.

"Mmmm, I love how you feel in jeans, the way you fill them out," she said as she felt the length of my shaft, the head poking sideways, a long bulge that reached over to my right thigh. We didn't do a lot of petting at my house; it was usually get naked-or mostly so-and fuck, though it was almost always with a loving feeling. It was really nice to have Jen playing with my dick through my jeans. She has a great touch, though sometimes I wonder that I don't cum without her ever laying a hand on me.

"It is nice-I love your hands on me. We have to do this more when you come over for coffee." My cock was now straining hard at my jeans, which Jen picked up on quickly.

"Mmmm, yes, we do. I love how you feel when you get so big. Now let's get him out of there..."

"Yeah, before you make him spew right where he is," I cut her off, making her laugh.

"Yeah, it won't take long, I can tell. You're really hard today."

I kissed Jen. "There's something about sex in a back seat that's really arousing to me. There's an urgency and rush to it that you don't get anywhere else. It's a kind of forbidden fruit, like you're getting away with something, or hiding it from your parents."

Jen laughed out loud. "Or your kids," she said, still laughing.

"Is that why we're here??" I asked, half kidding.

Jen looked at me. "Yeah, actually. My girls have the day off, some kind of teacher professional day or something, so they're home. I thought, if I get home, pull up in the driveway, then disappear into your house for an hour and a half, they'll wonder what's going on, and I really won't have a good answer-and they are pretty perceptive, so it's hard to keep things from them, especially when it's right in their faces."

"We could have had a quickie," I teased.

"You're so helpful," said Jen, kissing me through a giggle. "And the quickies are fun," she said, her eyes getting wide. "But still, I can't very well come home over an hour after I pull up the driveway, smelling like cum-and not their father's..." she smiled, her voice trailing off.

I laughed "Yeah, coming in smelling like 'who just got laid' is probably not a good idea."

"So, I thought we'd have lunch, and a little treat." Jen smiled. "And I haven't had sex in a back seat in more years than I can remember. Are you up for it??"

"I think you already know the answer to that," I said, making Jen laugh and stroke my hard dick again, which made a small wet spot emerge on the front of my jeans as she squeezed a drop of precum out. I kissed Jen hard, now reaching to her crotch, starting to rub her pussy over her thin panties. I could feel the full patch of soft hair under them, and I played over it for a few minutes, tracing the cleft between her legs, feeling it moisten as her arousal grew. I traced along the leg bands, feeling the stray curls that escaped their confinement.

Meanwhile, Jen had unzipped my jeans, allowing my cock to stand free, sticking straight up when she released it. She stroked gently while I played with her pussy. After a few minutes, she had me lift off the seat, and pushed my jeans down, freeing my balls as well. Jen loves to play with my nuts, fondling and rolling them in her hands, and she was soon working me hard, rolling them around in her right hand as I reached into her panties, pushing the leg band aside for access to her now well juiced pussy; all the time this was going on, we kissed lustfully.

I worked one finger into Jen, then a second one, dragging them over her clit as I finger fucked her. She alternately played with my balls and stroked my cock. Getting laid in a car has always been a turn on for me, and I was stiffer than I usually get with Jen, which is to say like a piece of rebar.

"Wow, you're hard," said Jen, noticing the obvious. "I don't know when you're ever been this stiff-and you're pretty hard when we're together." She smiled.

"There's something about having sex in a back seat that just gets me started," I told her. "Ever since my first time, over," I looked at her studiously, "40 years ago."

Jen laughed. "I was...never mind!!" She said, laughing. "Little then."

We kissed some more, and I pulled Jen's panties out from under her dress, down her thighs and over her boots, finally getting them off and tossing them on the front seat console. I ran my fingers all around her dark, full bush, ending up tracing her labia and lingering on her clit, making her jump. She was ridiculously wet.

"I think someone else likes making out in a back seat, too."

Jen blushed. "I was on the cheerleading squad in high school. My boyfriend and I never missed a chance at a game. Sometimes during a game." She smiled. "This is bringing back some fun memories."

"He was a football player??"

"No, he wasn't connected with sports at all. We just went to all the games-well, I had to, but he'd go with me anywhere." She smiled. "And the trips home were always fun. We'd tease each other til we couldn't wait any more, then find somewhere to pull off and screw like crazy. There's something about getting balled in the back of a Chevy while wearing a cheerleader skirt and sweater that's just unbelievably hot." Jen sighed. I could see she missed that aspect of her youth.

Jen kissed me again, and climbed atop me. She pulled up her dress, and I could see her pussy as she slid to me, her bush coming to rest on my dick. It was nice feeling her soft hair on me. Also nice was feeling the leather of her thigh high boots on my legs as she straddled me. We kissed again, and she lifted up, then I felt her labia moving over my cock, the head sliding on them as she positioned herself over me. She reached down, guiding me to her. The head of my dick slid over her clit, making her jump, and then I was in, going right to her cervix.

"Wow, you're so hard. I feel you poking my womb." Jen's clit hit my pubic bone as my cock filled her, and she sat up, her head rolling back, mouth open as the tension on her clit sent her into a quick orgasm, her hips shuddering as she came. I held my cock deep in her, then started to slowly move her up and down on me once she came off her short cum.

Jen picked up on my motion, and started riding. I was stiff as a post, something that screwing in a back seat always does to me. It wasn't lost on Jen, who was enjoying the added stimulus.

"Damn, your head is big today!!" She exclaimed, feeling my swelling cock inside her.

"I told you screwing in a car gets me heated up. And the leather on those boots is really pushing me along, too." It was. I could feel the leather on my thighs, and watching those 4" heels bouncing as Jen rode me was working me up as well.

"Yeah, but this is...mmmmph!!" Jen's hips jumped as the pressure of my pubic bone on her clit set off a shock wave. "Intense," she said, in a loud whisper. "And you feel like you're going to cum soon....MMMPHHH!!!" I ground into her clit at the same time my cockhead poked her cervix again, drawing another shock wave. Jen looked at me with lust and longing in her eyes. The ride she was taking on me was getting to her, as she'd already had a couple of short but intense orgasms.

She was right, though. I was getting close, and the head of my cock was swelling in anticipation of blowing a huge load into this gorgeous woman's supremely wet pussy. As much as we were enjoying this intensely passionate coupling, we also didn't want it to be over too soon. I grabbed Jen's hips, and slowed her pace.

"Easy," I said. "I know we don't want to linger here too long, but I'm not ready for this to be over yet." I pulled Jen down on me, her clit resting on the base of my cock. She again shuddered from the hard contact. I looked into her eyes, and kissed her deeply. I felt her body relax and fall into me, her full tits pressing into my chest. Her pussy again juiced around me as she had another small orgasm. She started to ride me very slowly, making my cock swell as she pushed down, driving the head into her womb. I could feel her pussy quivering around me from her cum, and it was having its effect on my dick.

I wasn't going to be able to take a lot more of this, and released the kiss, Jen out of breath in the aftermath of the long kiss and short orgasm. She giggled as she panted.

"That as hot. I love when we kiss like that. It's so...loving." Her eyes sparkled as she looked at me. "I love how you always make love to me, no matter how raw and lusty the sex is."

"Could be I'm in love with my sweet, sexy, neighbor," I said, only half kidding. I'd grown quite fond of Jen over the couple of years we lived next door to each other. "And she's a pretty hot lay, too," I said, kissing her.

Jen laughed. "Well, that's because my neighbor brings it out in me. He always makes me feel loved. When I feel loved, I get really into making love." Jen's soft brown eyes seemed to be looking into my soul. She kissed me, then leaned back. I could see my cock spreading her dark bush, her labia gripping my pulsing erection. As she leaned back, her body moved so that my cock was about halfway inside her. Between the added friction of her leaning back, and her vagina pulsing around me, I was about to lose it. I relaxed my butt, which supressed the urge to clench the muscles that would make my cock spurt.

Jen sighed as she felt my cock start to pulse more intensely. "Inside me," she said softly, as if there was any other option, given that she had me firmly ensconsed in her throbbing sex.

I felt the head of my dick swell, but just held still, letting it throb inside her. "Oh....Jen..." I said in a whisper. I felt a long, slow, surge of cum flow from my cock, slowly filling Jen's cunt, then slide down along my dick, some slipping out as the flow continued. Jen first giggled as she felt my cum start to fill her, then sigh as she felt the heat spreading inside her, then a longer sigh, her hips shaking as the heat fully engulfed her insides.

Jen closed her eyes and leaned back, the opened them, looking at me. "Ohhhhh....Tommmmm........" She again closed her eyes, and slowly sank down on my still oozing cock, which went all the way in her with a slurp as it pushed the cum out of her. "Aaaahhhhhhh......" Jen looked at me, her face contorted as she felt the heat of my semen and the fullness of my cock inside her. She fell to me, kissing me hard. I felt her hips start to work up and down, now moving steadily, my cum slurping as she moved.

"Your cum is so hot inside me, your cock is so big inside me. I want the rest of it, all your sweet," she kissed me, "hot," she kissed me again, "cum." She kissed me again, taking my face in her hands, kissing me deeply, her tongue trying to pull mine out of my mouth, so intense was her kiss.

I grabbed her hips and pulled her to me, grinding on her clit, making her kiss intensify. I had now pulled back from the edge of orgasm, but was still close to cumming. Jen's incredibly wet pussy, saturated in her own juice, and flooded with my cum, was making all kinds of sloppy noises as I worked her back and forth on my dick. We broke from our kiss, Jen taking a long breath and leaning back. I looked down, and could see my cock in her pussy, surrounded by a now wet and tangled bush, itself split by her spread pussy, her labia grasping my erect dick as she slid up and down on me, my cock slick and shiny with the essence of hot sex, a film of her pussy secretions and my semen coating it.

By leaning back, Jen made it so my cock reached only about half way into her pussy, the head getting just about to her G spot. I realized this, and started making short thrusts right there. The combination of that, and pressure on her clit, sent her over the top, and she yelped and her eyes got big as her orgasm started to wash over her like a tsunami, then her head fell back, her eyes closed, her mouth open to cry out, but no sound coming from her, til finally her hips shook violently, and she let out a long sigh, then a moan. She sat up, pushing her pussy back down on me, and came hard, kissing me roughly, whimpering through her kiss.

Her kiss lightened up as she came down off her orgasm. I was riding the wave now, and ready to cum. Jen pushed down on me once more, still kissing me.

"Cum inside me now," she said softly. "I want your cum, baby. Seed me..." Her voice trailed off as my cock pulsed and I came, shooting long bursts of cum into her womb, my cock was pushed up against it. I now intensified our kiss. I had one arm around Jen's back and pulled her to me to kiss her harder; the other hand on her bare ass, pulling it into me so I could get my cock fully inside her. Despite having edged into Jen's cunt only a few minutes earlier, I let go a flood of sperm, flooding her even more, my cum overflowing her, spilling back over my balls and the thick hair around them. I was going to need a shower when I got home, so soaked was I with the sexual fluids we'd both yielded in our cumming.

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