Driving Jackie Ch. 01

I tried to concentrate on what I was doing to her pussy, letting the feelings in my own organ move to the back of my mind. This was a lot easier said than done, the sensations in my cock were driving me crazy as she continued to move up and down the length of my shaft. With some effort, I managed to control my own impulses and focus my entire attention on the pussy I was eating. I ran my tongue up and down the lips, I brushed the clit every few strokes, I ran my tongue into the entrance to her vagina, and then I moved to the clit and sucked and teased it with the tip of my tongue. I was lost in the moment and the feeling of my tongue on her pussy was great when she slid her mouth down my cock as she had been doing, and then dragged her teeth along the length on the upstroke, catching the ridge below the head and giving a good tug before releasing. I jumped at the feeling, and Jackie stopped what she was doing, then spoke the first words either of us had uttered since lights out.

"Are you OK? I didn't hurt you did I?"

I had never experienced anything like this before, and although it had surprised me, the feeling was so intense I had a tough time speaking for a few seconds.

"No, you didn't hurt me. I wasn't expecting that, but please do it again, and don't stop!"

Jackie giggled, and went back to her previous task. The feeling of her teeth was amazing, and it was that exquisite feeling of pleasure that is just shy of pain. It is not something one can easily explain, it just has to be experienced to understand.

With the new sensations I was feeling in my cock, I wasn't sure just how much longer I would be able to hold out. I redoubled my efforts on Jackie's clit, and the increase in her moaning let me know I was getting her closer to her pending orgasm. She had been humping my face for the last few minutes and the speed of her thrusts increased, as did her vocalizations. I knew she was close, and while continuing my mouth action, started squeezing and pulling at her ass cheeks, positioned above my face. I had my hands wrapped around her thighs and up over the top of her ass, so my fingers dug into the crack and I pulled further apart. This was the encouragement she needed, and she started coming with a moan deep in her throat and her entire body trembling on top of me. I continued to lick, slowing down my efforts, but keeping the stimulation there to allow her orgasm to wash over her for as long as she wanted it to continue. Her voice seemed to disappear, instead her screams just caught in her throat uttering a primal gurgling deep within her body. She had stopped moving her mouth on my cock as the orgasm overtook her, but it was still safe in the warm, wet mouth that had lovingly caressed it for the past minutes. I slowed then stopped my actions. I allowed her a few minutes to come down, just holding her and gently moving my hands over her back and ass. Soon she was able to regain the use of her voice, and commented "That was amazing." She was still breathing hard, but I just kept holding her and moving my hands on her warm skin, now slightly damp from the exertion.

I waited a minute more, and then rolled her off me. She had started sucking my cock again, but when I moved she let me go, and I turned around to face her once again. I kissed her hard, and she returned the kiss with more passion than we had shown earlier in our session. She put her arms around my back and pulled me close. As we kissed, her hand went down to my still stiff cock lying trapped between our bodies. Grabbing it in her hand and squeezing, she said "I think that we still need to do something with this."

I wasn't going to disagree, and moved to get up on my knees between her legs. I was surprised when she pulled her legs up to her chest, her thighs resting on her breasts, crushing them to her body. Her pussy, wet and slippery, invited me to enter, and despite my curiosity about her leg position, I pushed forward and slid in easily. As I started thrusting in, she would use her legs to push me away. This was really strange, and I had never experienced anything like this before. Jackie was giggling a little, I assume she understood my puzzlement, and just let me wonder. I realized that if I wanted to stay inside her, I had to hold onto her tightly and work to get back in. she was going to make me fight for this, and in a strange, almost masochistic way, it was exciting. Not only was I feeling the sensation of my cock sliding in and out of the wet pussy, but I was holding on to her torso tightly, working hard to maintain our contact.

Jackie started talking to me then, encouraging me to work harder.

"Give it to me, Steve. Keep it in there, you know you want it!"

Every time I stroked into her, she would push me away with her legs and I would have to force my way back in. the effort was sucking some of the energy out of me, but I wasn't going to not succeed. I pushed in harder and she pushed back harder still. I was grunting and straining, working for every centimeter of pussy I could get. Jackie continued to urge me on, exciting me with her challenges.

"Come on, give it to me! You know you want this pussy, work for it. Fuck my pussy, it is waiting for you to fill it up!" As she said this last, her voice got tight and I heard the now familiar growl coming from deep within her chest. I knew she was coming and felt a tingling in my balls signaling my own imminent orgasm.

That was all I needed, I buried my cock inside her and held on against the resistance her legs were offering, spurting hot semen deep into her insides. Jackie felt the spasming of my cock and stopped trying to push me away. She wrapped her legs around my waist and forcing the words, told me to fill her up.

"That's it baby, give me all you've got. I knew you had it in you."

The experience was intense, and I wondered to myself where this wilder side of Jackie had come from. Although we were just friends, I had not seen anything from her at home to indicate that she was not the sweet, friendly young woman I knew. Still, I wasn't going to complain, especially since we still had a few more days together before heading back.

Once my breathing and heart rate had returned to normal, or at least as close to normal as they would get for a while, I started to pull out. Jackie still had her legs wrapped around my waist and as I started to move away, she put her heels down behind my ass and said "Don't go! I want you to stay with me."

I settled back into her pussy, pushing my still semi hard cock back as far as I could get it. Jackie sighed contentedly as we lay there. I did not want to leave my weight on top of her, so I rolled us together and ended up under her, supporting her weight with my own body. Jackie giggled as we moved, but we maintained our connection.

"This is nice. Jackie put her head on my shoulder and kissed me on the cheek softly. I wrapped my arms around her back and pulled her even closer to me, if that was possible. I felt her breathing slow and become more regular, realizing that she had gone to sleep. Surprisingly, she seemed almost light as she lay on top of me. I again wondered what this would have been like in the light, I really wanted to see her expression as we had given each other pleasure. I promised myself that if (hopefully when) this happened again, I would be sure to leave a light on. I guess I needed some reassurance that I had made her feel as good as she had made me, but I think I already knew the answer to that. Pondering these deep philosophical questions, I too soon drifted off myself.

*****

I woke up realizing that Jackie was still lying on me, still asleep. I further discovered, to my own amazement, that my cock was still deep inside her pussy. I would have bet money that I would have shrunken and then slipped out, but no. This was fascinating and I took a moment or 2 to enjoy the feeling. My cock was still surrounded by the warm and wet feeling of the pussy I fucked a few short hours ago. Jackie lay on top of me, not heavy in the least. Her breathing was soft and regular, seeming to be totally at home lying naked on top of me as she slept. As I was thinking about the implications of this situation, my cock decided that it was time to regain some of its former size. I could feel it slowly growing inside the walls of Jackie's pussy, and the feeling was one I wanted to experience in minute detail. Each centimeter of growth gave me new electricity running through my cock, and as I continued to lie here, I noticed that Jackie's breathing had become a little faster and less regular. I assume the nerve endings in her pussy were being stimulated as well as the nerve endings of my own tool. I had an urge to start thrusting up into her, but after the long, tiring day I knew she had, I did not want to wake her.

As I lay there experiencing the strange sensations, my cock gave an involuntary twitch as it neared full erection. Jackie missed a breath, and then I heard a soft moan from her lips. Still, her breathing settled down to more regular again and I knew she was still sleeping.

I had been holding her the entire time, and held her more tightly now. She continued to sleep on, offering a contented sigh as I adjusted my hold on her. I decided to try something, and with a little effort, I started tensing my cock, and then relaxing. As I started to get into a rhythm, I noticed Jackie's breathing getting more irregular, with soft sighs and moans coming from her, although she did not move or show any signs of waking up. I found this very interesting, and the feeling of my cock inside her, twitching and moving slowly with only my own muscle control as stimulation, my excitement was growing. After a few more twitches, Jackie moved a bit, but only to reposition herself slightly adding another sensation to my over-stimulated member. Her low moans and sighs had continued and I wondered if she was dreaming about what might be happening, or if subconsciously she was experiencing the same pleasure I was. Thinking about the implications of what was happening and what might be going through her mind, I felt my balls contract and soon I was sending another volley of sperm into Jackie. As my cock was twitching and pulsing within her, Jackie murmured some low unintelligible sounds, but did not wake. Her breathing returned to it former regular pattern, and I just lay there feeling the glow of my cock starting to wilt slightly while still surrounded by the warm and recently wetter walls of Jackie's tight pussy. Amazing, I thought to myself. I wonder if she will realize what happened when she wakes up. I decided not to spend too much time wrestling with such deep questions, tomorrow would be time enough to discover new facts about our time together.

*****

I woke about 5 seconds before the alarm on my cell went off. I normally got up at 6 while on the road, and although I did not need that much time to get ready for the day, I found this pattern to work well for me. Sometimes I would get breakfast on the way out, or perhaps spend an hour in the hotel's fitness center. Today, I had no such plans, just got up due to habit. Jackie was not lying on top of me as I woke, so my cock had slipped out of her sometime during the early morning hours. I marveled at the thought that I had been able to stay hard enough to remain inside her for as long as I had. Definitely something to try again in the future.

Jackie woke up hearing the alarm and with her eyes barely open, snuggled up to me and gave me a kiss on the cheek. I said I was going to get a shower, but she said it was way too early to get up. I laughed, calling her a lazy bum, and headed into the bathroom. I started the water running, and as I was adjusting the temperature, I heard a muffled shout from the other room. "Wait for me!"

Jackie came into the bathroom, naked and looking damn nice. Her hair was a tangled mess, but even the sleep still on her face could not disguise her attractiveness. She gave a weak smile and again wondered how anyone could get up at this insane hour. I assume she needed to be up herself for work at home, but on vacation, she seemed to be moving more slowly.

"What do you mean 'lazy bum'?" she asked with a little smile.

"You were the one who wanted to stay in bed. If the shoe fits..."

She stuck out her tongue at me, and then I pulled her into the shower with me. She squealed a little as I tickled her sides, but the warm water allowed her to relax and she put her arms around me and hugged tight. I could feel my erection getting bigger, and the thought of another session with her before work was appealing, but I knew I would get lost in time if I allowed that to happen. Still, we could play slip and slide on each other for a while, and then have a game of hide the salami later this evening. And that is exactly what we did.

I finished dressing, and then got my gear together. Jackie was still wandering around the room naked, trying to tease me a little, but we both knew it was a game and that it would continue later this evening. Certainly something to look forward to. I left Jackie the keys to the rental car and the GPS I usually brought with me. I told her to have a good time and I would be back later in the day. She gave me a lingering kiss as I was heading for the door, and I couldn't resist a quick grope of her breasts, followed by a smack to her ass, telling her to get dressed!

The cab dropped me off at the client's site just after 9. As I had explained to Jackie last night, there was a tray of Danish and a large urn of coffee in the computer room. I greeted the colleagues I would be working with later this morning before helping myself to a cup of hot coffee and a cheese Danish. I needed a second Danish to help me get some of my strength back from the exertion of last night. The coffee would be a continuing need. Our planning yesterday had paid off and the install went quickly and smoothly. I did not expect problems, although this application was customized to the client, I had developed the framework years ago and had polished and evolved it to the point of having most of the bugs worked out. We spent the balance of the morning and the afternoon trying to break it, all without success. Migrating the data from the old database and populating the new one would take the better part of 8 hours, so we set things up and kicked off the process just before calling it a day.

The cab dropped me back at the hotel just after 5, and as I got out, I saw Jackie handing her keys to the valet. She was wearing a bright yellow sundress with spaghetti straps that bared her shoulders. I noticed the dress was short enough that I got a good view of her legs and since she normally wore jeans at home, I realized just how nicely shaped they were. The valet was also taking notice as Jackie started toward the hotel doors, then changed direction to meet me as I called out to her. She gave me a big hug and warm kiss, pressing her body to mine in greeting. I saw the valet still checking her out, and wrapped my own arms around her, giving her ass a little squeeze and keeping my hand there a bit longer than might have been necessary, but I was putting on a show for the valet. Besides, I enjoyed the contact and Jackie did not complain.

We went up to the room together and each disposed of items we had been carrying. Jackie set her purse down and I removed the coat and tie, placing my laptop near the small desk. Jackie then came over and gave me a better greeting, this one lasting longer than the one we exchanged outside. I guess she was glad to see me, and I had to admit to myself I missed her as well. I stepped back to admire her and got a good look at the dress. It fit her well, but she did push it out in all the right places. She saw me looking and spun around slowly allowing me to take it all in, smiling as she saw my appreciative expression.

"Like? I bought it just for this trip. I was hoping the weather would be nice enough to wear it."

"Yes, I like it! Very nice and it certainly does you justice. I know when we go out tonight, anyone seeing us together will be very envious of me."

Jackie blushed a little, but smiled broadly at my compliment. "Do you have any place in mind for dinner? I skipped lunch, I was not too hungry today, but now I am starved."

"I don't have any place in mind, but thought maybe we can get some ribs and BBQ if you like that kind of food. What do you think?"

"Sounds great. When do we leave?"

I was ready to go, but like any woman, Jackie needed a few minutes to take care of her hair and touch up her makeup and lipstick. 20 minutes later we were on our way downstairs, making a stop at the front desk to get a recommendation for dinner. This restaurant was a little further away than the one last night, so we had a cab come by to pick us up. The drive took about 20 minutes, and we chatted about our day as we took in the city while we drove.

The restaurant was less formal than the steakhouse last night, and the crowd was doing its best to have a good time. The general level of conversation and merriment was more intense than last night, and everyone seemed to be having fun. We were seated and the waitress came by for a drink order and left us menus and bibs. We each ordered a beer, something that seemed more appropriate to ribs than wine. When the waitress came back with the drinks, we each ordered a large rack of ribs with all the fixings, the smell of BBQ making us hungry beyond our normal expectation. While we were waiting for dinner to arrive, I looked at the crowd and saw everyone was having fun, eating and drinking as the music blasted out making conversation difficult. We had to move closer together to talk, but that is not a bad thing in my book. Jackie told me about a couple of museums she had seen and I gave a brief overview of my day, not wanting to bore her with technical details.

The ribs arrived and we stopped talking long enough to get to work on the food. I hated to see Jackie put on that large bib, but slopping sauce over her new dress would not be a good thing. I had been taking notice of her breasts as we talked, and I was not the only one as many of the patrons had checked her out as we came in. I could see the look of envy on some of their faces, and felt a sense of smugness inside knowing she was with me. I let these thoughts go long enough to divert my attention to the food and did not come up for air until the plate was done. Jackie was doing the same, and except to order another round of beer, neither of us said anything for some time.

After the plates had been cleared, I looked at Jackie and she at me, and we each knew we had eaten too much. The food was great, and speaking close to her ear to be heard, I suggested we stay here for a while before trying to move. Jackie agreed, and we vegged out for the next hour. Fortunately, there were empty tables so we did not put out anyone waiting, and we each ordered another beer. When we did leave, I left a very nice tip for the waitress, I know they don't make a lot of money when someone monopolizes one of their tables for an extended time. As we left, I suggested in jest we walk back to the hotel, but it was a bit far. We did walk around the area for the next half hour to work off some of the fullness before calling a cab to take us back. The ride was quick and uneventful, and before we knew it, we were back in our room.

The evening had been another great one even though conversation was difficult in the restaurant. Walking around downtown, holding hands and just enjoying each other's company had made the evening very pleasant. Now we were back in the room, just about the place we were last night when things got interesting. Now, however, there was not any doubt or uncertainty about what would happen as we went to bed. Jackie untied the straps to the sundress and it slipped to the floor, hanging up for a second as it slipped past her breasts. She was wearing some kind of half bra thingy and matching panties underneath, but the bra soon followed her dress toward the floor. Once again she was standing there in front of me in just her panties; this was getting to be a habit. I started removing my own clothes, but Jackie quickly volunteered to take over for me, and I wasn't complaining. She unbuttoned my shirt, then carefully pulled it off and laid it on the chair. Next came the pants, again folded neatly on the chair. Before I knew it, I was standing there in just boxers with my cock starting to feel a little larger and more crowded under the cloth. Jackie gave it a quick squeeze in appreciation and I felt it twitch and grow some more. No email or weather forecast tonight, we each knew what we wanted and were anxious to get started.