Top Twenty #05: Jenna Pt. 01

I dialed the City Paper voice mail box number, 55-MATCH, punched in my code and listened to the replies. "You have one new message: A sweet-voiced girl with a Texas drawl said, "Hi, this is Jenna, I'm twenty one, moved here recently from Texas and I liked your ad. A little about me, I'm 5'5", pretty, with medium length blonde hair and a slim build. Just like you, I like going to concerts and cooking and I love to dance and go clubbing. And in response to your interests, yes, I love wearing high heels, stockings and miniskirts. I hope to hear back from you. My number is 202-555-2470.". I listened to the message again and wrote down the number. She certainly had a sexy, Texas-style drawl in her voice that made it easy to listen to her message again. I called her the next day and we had a good conversation and we agreed to meet that Friday for a casual drink/date at an outdoor cafe downtown after she got off work.

She wasn't hard to spot, an attractive, slim blonde, looking just like her description and wearing sexy-styled business attire, a fitted, navy blue women's suit, both a well-tailored jacket and matching, slim skirt that ended a few inches above the knee and paired with nude stockings. The look matched her occupation, she had told me during our phone conversation that she was the store manager ar a copy and fax store in the downtown district, not too far from my office. Best of all, was her choice of footwear, simple, black leather pumps with pencil-thin, 5" stiletto heels.

The tailored business suit accented the slim, tight body she said she had on the phone. We hit it off immediately as she sat across from me twirling the stir in her double-strength vodka-tonic on the outdoor patio. The bar was a locals place and served mix-your-own style mixed drinks. Essentially they brought out a highball glass full of ice and liquor and a separate mini-bottle of mixer. No regulars drank beer or wine in this place, the cheap, strong drinks were the main attraction, along with the patio for people-watching in this busy neighborhood. True regulars sat at the inside bar, but I preferred the people-watching perch of the outdoor patio.

My bourbon and coke was served as a tumbler glass nearly full with ice cubes and syrup-colored brown bourbon with a stir straw in it. The mixer was served in an 8 ounce "mini" bottle, in my case, a red-labeled Coke. To my mix of pleasure and admonishment, telling Jenna to order a mixed drink wasn't necessary, she turned out to be a devoted vodka and tonic fan. Our drinks arrived and after opening our mini-bottles and pouring an ounce of mixer into the nearly-full glass, our drinks were rim-full and throat-burning strong. Sipping the drink while leaving it on the table was necessary to keep from spilling the alcohol, ice and splash of mixer cocktail. As we sipped our drinks, we hit it off immediately with small talk about our similar stories of transplanting ourselves to Washington, DC and our "two drink" casual meeting turned into a longer date that included appetizers from the kitchen to control the quick buzz we both caught from drinking our stiff drinks on an empty stomach. As the late summer sky turned to a deep blue twilight, I mentioned that I had VIP tickets for a club opening later that night, and asked her if she'd like to extend the date with me by going to the dance club's VIP opening. She was clearly eager and excited to go, and mentioned that she had read about the new club's debut in the weekly City Paper, but she told me she wasn't dressed for clubbing and wanted to go home and change before going back out.

We finished our drinks as the night took over the sky and took a cab to her house so she could change. Her place was outside the city, a twenty minute ride uptown and I waited down in her living room while she went up to her bedroom and changed. When she came down the stairs five minutes later, she was now wearing club attire. She had replaced her sexy business suit with a tiny, white, rouched minidress that clung and stretched over her firm tits, slim hips and narrow waist. The dress did nothing to hide her body and drew attention to her trim, sexy ass and long, lean frame. The dress was sleeveless and super short, stopping just a few inches past her ass and showing nearly every bit of her long, slim legs now encased in shimmery, silver-toned stockings and a pair of silver 5" pumps, identical to the ones she was previously wearing other than the color. With the taxi idling outside on the fixed hourly rate of the zone cab system, she had made her outfit change very quick and within 5 minutes of arrival, we were back in the cab, headed again downtown.

Damn, she looked smoking hot, that dress was a tiny thing and the rouching and spandex in the dress caused the hem to pull upwards as she moved. The dress clung to every inch of her body and she went from sexy business girl to club hottie in her five minute outfit change. The night just went from good to great in the last 30 seconds as i took her hand and opened the car door to the idling cab that waited for us for his round-trip, $60 fare.

When she sat down and scooted along the back seat, her minidress that barely covered her ass and made her legs look fantastic went up her thighs a bit more. As she crossed her legs, her dress crept up higher still and now barely covered her sex and showed off every bit of her stocking-covered legs and shiny, glittering pumps. I thought that Jenna had to be wearing pantyhose because otherwise her stocking tops would be visible with her dress this high up on her slim, firm, young thighs. A bit buzzed and feeling comfortable with me, she snuggled up against me for the 15 minute cab ride back downtown to the club and I felt my cock stiffen as she put her hand on my thigh and gently ran it up and down my leg. Her hand went from my kneecap up to mid-thigh, stopping each time just an inch or so from my now-prominent erection lurking under my slacks. Her long nails glided up, then down my leg, occasionally giving my thigh a squeeze as we rode along the pot-holes and bumps along Georgia Avenue. From her thigh caress and my hand around her narrow waist to pull her against me as we sat in the back seat, I felt an alcohol-enhanced mutual attraction. Three hours into our date and I was snuggling against a hot, young blonde wearing a barely legal white mini dress and silver fuck-me pumps and we were heading to a VIP event at a nightclub. Things were looking very good for a personal ad blind date.

We got out of the cab and I forked over $60, figuring it was my date and I should cover the cost of her attending the club opening. We got into the club using my VIP invite quickly, bypassing the line of guests without special invitations and quickly found a bar. We ordered more drinks to regain our good buzz as the music pulsed loudly and shook the air around us. It was busy, but Jenna didn't have trouble getting the bartender's attention in her skintight, white dress paired with her blonde hair and big, dangling earrings and ordering us two drinks that were part of the complimentary invitation. I made sure to tip the guy $10 so he could remember me later. We took the fresh drinks out onto the dance floor and danced and ground against each other until she had worked up a healthy glow and I was sweating hard. I took every opportunity to press up against her as we danced and she did the same, making sure I felt her tight ass rubbing against my fully-hard cock as she backed up against me and wiggled her cute, tight, barely covered ass into my slacks. She didn't seem to be surprised at my erection rubbing along her ass as we danced and so I didn't try and hide it from her.

We left the main dance floor and explored the club, going into the basement "House/Trance" room and upstairs to the "Disco" palace. A few hours and three drinks later we were very buzzed and sitting on two plush chairs near the wall when she reached up my leg with her manicured nails and gave my semi-hard cock a squeeze as she leaned in and said, "isn't it about time to go back to your place?". While I knew the date was going well, I wasn't really expecting to take her home tonight. She lived in the exact opposite direction I did and it was our very first meeting, but I wasn't opposed to the idea, just surprised.

I didn't need any further hints about what Jenna had on her mind, but we had missed the last Metro train back to my house, so we hailed a cab outside the club and kissed and made out as the cabbie drove us 10 miles to the house I shared with two girl roommates. It was Friday night so one of my roommates would be at her boyfriend's place and the other was usually asleep by 2AM no matter what night it was. As Jenna and I entered the townhouse after paying the taxi driver, we tried to be quiet. Jenna went quietly upstairs to use the single bathroom in my place and came back down without her stockings on and carrying her stilettos in one hand.

"I didn't want to wake anyone." she said as I looked at her carrying her shoes down the stairs and came to the couch and sat in my lap. She had slipped off her nylons while in the bathroom and her bare, smooth legs felt amazing as I ran my hands up and down them. She started kissing me again as my hands explored her minidress-covered body and her lean legs After a few minutes of mutual groping, she asked, "Where is YOUR room?" and I got her off my lap, stood up and led her through the kitchen and down the stairs to my basement level bedroom. Once we got downstairs I said, "I want your heels on." and she gave me a knowing smirk and dropped them onto the floor and wiggled her feet back into them. She instantly grew nearly five inches and stood there posing and showing off her legs as I moved to her and kissed her lips hard again. The heels made her nearly my height as I slid my tongue into her mouth and moved her closer to my bed. When we got to my bed, she sat down and her hands went quickly to my zipper, tugging on it and unbuttoning my pants, pulling the zipper and my pants down as she worked my belt off and then pulled at my suit pants. She knew what she wanted and was ready to go after it.

"It's big!" she said approvingly as she used her hand to stroke my cock through my underwear. "I knew you were big when I saw the bulge..." She pulled the tip from my boxers, stared at my cock and announced, "It's nicer than I imagined." she said with a smile as she pulled the rest of my erect cock from my underwear and exposed it in the barely lit basement bedroom.

"You like me in high heels... And I like a man with a nice cock." she said as she licked up the underside of my stiff dick with the tip of her tongue. I reached down into her dress and felt her hard nipples.

"No bra?" I asked.

"Strapless bra, but I took it off in your bathroom, along with my panties and my hose." she said before giving my cock another lick from base to crown.

"Nice. I like your nipples, so hard and perky, and I love your firm, hard tits. I love how they stand out." I said, pushing the top of her dress down off her shoulders and exposing her hard, firm, b-cup titties to the air.

"They are sensitive, I like them rubbed and sucked, especially my nipples." she said as she licked around the crown of my cock then stroked my shaft with her nails and fingers. She knew how to use her mouth, taking her time and extending the foreplay with licks, kisses and teasing sucks rather than just taking me into her mouth for a mechanical, up/down/up/down suck. She blew on the head lightly and then licked the pre-cum from the tip before swirling her tongue around my swollen glans.

"Mmmmm, I love sucking on a big, thick cock. Makes me soooooo wet. Feed it to me." she said as I brought my hands up to the back of her head and pushed her lips onto my aching, leaking cock. She opened her mouth and accepted the head of my cock into her warm, wet mouth but I didn't thrust into her mouth as she asked me to. I kept my hips still and let her head move back and forth as I kept a grip on her hair, allowing her lips to go to the corona and then back up to the tip, letting her suck a bit more of my cock inside her mouth than the initial bob but keeping her lips from going down onto the meaty part of my shaft by holding and controlling each bob with a handful of her blonde hair. I was drunk, horny and getting my knob tip expertly polished by a hot, enthusiastic, blonde oral-sex princess who obviously enjoyed giving great head. She started to really get into it, bobbing up and down slowly on the head and then pressing forward at the nadir, trying to get an extra little bit into her sweet mouth. After a few minutes, she had about half of it in her mouth on each pass as I held on to her bobbing head to keep her from swallowing more of my aching cock. She kept her eyes up, looking at my face as she worked her lips up and down the shaft of my sensitive cock. She was amazing and she knew how much pleasure I was getting as she blew me, but I just had to tell her.

"You're fucking amazing." I moaned as she polished my helmet with her tongue and soft lips. I could see her eyes light up at the praise. "Fucking feels sooooo good baby. Keep sucking on it. I love having my cock sucked well and you are doing it VERY well. You like sucking my cock, don't you?"

I got an enthusiastic nod and "mmmhmmm" from Jenna as she kept slurping on my rod.

"It feels soo good baby and I have lots of control so keep sucking me". I begged as she took me a bit deeper than she had been. "Can you take it all in that sweet mouth? Down to the base? Are you a deep-throat girl? Do you like getting it down into your throat?" I said as I felt her push her lips further down my aching meat. She was definitely trying to take 5 inches of my big cock into her mouth and was leaving 2 or 3 inches out of the party in her mouth. I was impressed so far.

I kept my cock in her mouth as I bent down and pushed up on the hem of her minidress, pushing the dress past her legs till the bottom part was bunched around her narrow waist and exposing her shaved smooth pussy.

"Mmmm, bare. I like that. So sexy!" I said, commenting on her bald cunt.

She took my cock in her hand and began to stroke me. "Mmm, glad you approve, I find it helps me cum easier. I love being eaten and my last boyfriend seem to love munching my bare pussy. He's gone but I decided to keep it clean and bare.". She spread her legs and showed me even more of her swollen sex as I felt her hand stroking my cock and her mouth took me back inside as she applied suction to my stiff pole.

As I watched her spread her pussy open for my viewing pleasure, I felt her lips slide along my shaft as she sucked harder, hollowing out her cheeks as her lips went up and up to the tip, where she let it pop free with a slurp and opened her lips slightly before kissing the tip of my cock, preparing to take me back into her mouth for another vacuum suck.

She paused with her mouth and shafted my cock with her palm as she looked up and addressed me, "You may not believe me, but I'm not a slut. I don't fuck just anyone and never on the first date.".

"Never?" i said with a smirk.

"Close to never after tonight." she said and then she gave my cock a quick slurp with her mouth before continuing. "I haven't been fucked in three months, since I left Texas and my ex-boyfriend. And I like you.". She took another slurp on my shaft, almost like taking a hit from a bong. "And I like this! Big, but not too big." she said, kissing the tip and swirling her tongue around the glans. "And now that I'm in your bedroom, mostly naked, I'm going to show you what I like to do for the right guy. I'm not promiscuous, but I love being naughty." She jerked my cock again, then sucked on the tip.

"mmmm, baby, I LOVE naughty girls. It's why I like women who wear high heels and short skirts. I like a woman who likes looking and feeling sexy.". I stroked her cheek and flicked my thumb against her nipple.

"That's me, your ad said it. I love wearing high heels, stockings and short skirts. Naughty and sexy. I like the attention."

She sucked on the tip of my cock again, tasting the leaking pre-cum as she took another bong-hit like suck on my stiff cock. She took a second suck, this one longer and sweeter as she slid more of my fat, hard cock into her sweet lips.

She held my cock and gazed at it as she said, "Mmm, you just described me. I like to show off. I like it when guys look at me, want me. I love wearing high heels, especially when I'm the only girl wearing them in the room. I know my legs look extra sexy in them. Another thing? I like to please. I love making my man happy. I like to dress sexy because I like the attention of my guy. and I'll wear ANYthing you really want me to wear. This dress and these heels, I loved wearing them tonight because I could tell that you were hot for me. You were fucking me with your eyes as soon as i walked down the stairs wearing this dress."

I pushed her head back to my cock and she knew what i wanted, and so she went back to work on my cock, slurping, sucking and licking me furiously as she coated my shaft with her saliva. fuck, it felt SOOO good as she worked her magic on my stiff prick as i just stood up next to her and let her blow me.

"So if you like to give head so much, does that mean you swallow too? I asked as she bobbed up and down.

She paused again, "I love pleasing my guy, that means I like feeling you cum for me. I love to suck cock and it means I also swallow. Less mess. But if you cum, I want you to cum on my tongue, not down my throat. I like the taste of cum too. But if you cum in my mouth, I'm going to expect payback. You'd better eat me and fuck me afterwards. No falling asleep." she said before closing her lips around my cock and taking me into her mouth and eagerly downing my cock deep into her eager throat.

She sucked up and down a few strokes then paused, "I'll keep the heels on too, but you'd better fuck me good. Now enjoy my mouth on your nice cock. Fuck my mouth, or just sit there while I work on your cock. However you like it, as long as you cum nice and hard for me." she said before resuming her assault on my cock with her wet lips.

I let her fuck my cock with her mouth, licking it with her tongue as she sucked gently on the corona and tip, then watching as she bobbed her head up and down and took inches into her wet, soft mouth as she licked the sensitive underside of my cock. She liked to look up at me, make eye-contact and see my reaction as she did all kinds of things with her lips, tongue and mouth. She took it out and slapped her lips and cheek with it, then sucked on it again, then beat the tip of her nose with the tip of my cock and then sucked and swallowed my raging cock again, taking me deep into her throat, deeper than she'd taken me before. Then she took it back out and slapped it against her pursed lips as she looked up at me and gave me a raised eyebrow look and then moved her lips down the shaft, kissing down towards my balls, then licking and sucking on my sensitive, tight balls as she massaged them with her long nail tips.

"My man wants to cum soon, doesn't he? Gonna give me a big load in my mouth, aren't you? Your tight balls want to release soon, don't they? Go ahead, cum for me, cum in my mouth baby, let me taste your first, thick, sticky load of cum."

That's when I lost it and started to cum, she pushed her lips over the tip and began to collect the cum from my pulsing cock, squirt after squirt pulsed into her mouth and she just held her lips around it and gently sucked it as I unloaded my pent-up load of thick creamy sperm.

She waited until it was all out, sucking on the tip to get the last few drops and then took her lips off my mouth, looked up at me and opened up, showing me a pool of cum on her tongue, thick, creamy and swirled white, the cum stood up on her tongue like frosting. She smiled, smirked and then swallowed gently, tasting it as it went past her taste buds and into her throat.