Jeri and Roger: The Beginning

Jeri and Roger meet for the first time and enjoy what people almost twenty years apart in age can only dream about. What follows is a night that neither will forget. This story introduces a character that will be developed later. I am not a professional writer and this is just intended for fun.

Jeri: I did not know Roger well, and was not at all sure why the two of us had been selected to attend the convention. We were seated next to each other on the long flight, and were conversing easily. I was beginning to really like being with him, even though he was several years older. I had always been attracted to older men anyway, enjoying their confidence and self-assurance, and their knowledge about how to get what they wanted from women. The last stretch of the flight prior to landing had been very turbulent, and I found myself tightly clasping his hand for reassurance.

After collecting our luggage, we took an UBER to the hotel, checked in, and agreed to meet in the lounge later for a drink prior to attending the meet and greet scheduled for that evening. I unpacked in my room, took a short nap and then a long relaxing bubble bath. I kept thinking about Roger, and felt a definite attraction, which I was not at all sure that he shared. I decided that business-casual was the appropriate look for this evening, so selected a tight black skirt which was long enough to fall below my knees, a beige blouse cut low enough to expose some cleavage without appearing slutty, panties and bra, and tan hose with a garter belt and conservative two inch heels.

When I entered the lounge a few minutes later, I saw that Roger was already seated in a booth, so he waved me over and I slid in across the table from him. Roger made a nice comment about my appearance, and I though he looked very handsome tonight, wearing slacks, a sport coat, and nice shirt with no tie. We ordered drinks and chatted easily, getting to know each other better, and I found that I was really enjoying his company.

We each had a couple of drinks and then went into the convention center attached to the hotel for the evening festivities. There were several bars, tables laden with all kinds of snacks and finger foods, and a huge crowd. Later in the evening, a band began to play and Roger asked me to dance, which we did for quite a while. I enjoyed being in his arms. We were both just a little bit tipsy, and I was being a real flirt, pressing my body tightly to his, wiggling my hips, and rubbing my breasts into his chest. We finally decided to take a break, and he led me out onto a balcony for some fresh air. We were enjoying the sight of the lights of the city, when he put his arms around me and pulled me into him for a long passionate kiss. I felt my pussy give a little gush as his tongue dug into my mouth and his hands rubbed my ass cheeks. I felt any will power that I had ebbing away as my passion soared. His confidence was overwhelming my weakened defenses and I knew where this was leading. I just hoped we would get there soon!

Roger: I had seen Jeri at the office many times but really did not know her. Heck, I didn't even work for the company but was a hired consultant brought in to advise the owners on how to make the technology work and to handle any other issues that they could not deal with. The convention was a little off of my typical beat because it was a business conference and not the typical technical conferences where I was so often the speaker. It was in a nice location, close to the beach so I had decided that it would be more like a tropical vacation -- sun, surfing and bikinis. I guess since the company reservationist had booked the flights that Jeri and I wound up next to each other on the flight. I had noticed her long brown hair, beautiful sparkling eyes, trim figure, perfect heart shaped ass and firm B-cup breasts before but knew that I was too old to ever be with someone as gorgeous as her. I was, however, very glad to be seated next to her on the flight and looked forward to staring into those gorgeous eyes and hearing her sweet voice. Her perfume was an aphrodisiac to me.

She talked about everything and nothing at the same time during the flight. I honestly could not tell you what specifically she said because her voice had me hypnotized. As we started our descent, the ride got pretty rough due to an approaching tropical storm. She grabbed my hand, which was lying on the armrest, since she was so nervous. I was amazed at the softness of her skin. It sent waves of electricity up my arm. It was then that I was glad that I had my jacket in my lap because I was hard enough to cut diamond.

After we were on the ground, we made our way to baggage claim and retrieved our bags. She asked if we wanted to share a taxi, which I accepted, but I let her know that when I travel, I usually get a rental. We rode to the conference center hotel chatting the whole way while sitting a little closer than I would have with a fellow male traveler.

After we checked in, we both went to our rooms to freshen up and get ready for the conference pre-meeting festivities. I couldn't stop thinking about her but knew that she was far too young for me. She wasn't too young for my fantasies though and I thought that if I were younger, she would be the perfect girl in both her physical build as well as her bubbly and amazing personality. I could at least enjoy some time with her during the next few days.

When we met in the lobby, I was again amazed at her beauty but a little disappointed in her conservative dress. It was a business conference though with folks worried about accounts and contracts and not the high tech crowd or the strategic planners to which I was accustomed. I had worn the business appropriate attire as well. I desperately wanted to see more of her sexy legs and incredible figure.

When she arrived, I had already gotten us a booth and she slid right in, far enough away to be respectable but closer than just for a business chat. We talked about work, beaches, cooking, music and drinks. I ordered us both Blue Hawaiians and we laughed. She even laughed at my terrible jokes. When she laughs, her breasts bounce and I could not help but notice. After a few drinks, we were both a little tipsy and decided to dance.

As we danced, she molded herself into me. She could obviously feel my arousal and as we slow-danced pushed her mound into my erection and was grinding harder and harder. As we continued, she moved her lips to my ear and whispered gently in my ear. We stepped outside and I kissed her, first gently, and then more forcefully allowing our tongues to explore each other. I would have taken her right there on the dance floor but that would have to wait until later since we did have an audience. After a few more dances, we walked back to our table and she slid in motioning for me to join right next to her. As I did, I gently put my hand on her leg but through her long skirt. She reached down and lifted my hand, hiked her skirt so that my hand was under it and placed it back on her leg. She looked me in the eye and said, "Please tell me all about yourself."

I looked at her and said, "You won't believe me if I do, but here goes the Reader's Digest version. Mentally you will be surprised how intelligent I am. I am rarely ever fooled or fail to notice things. I don't work for the company but just consult for them on occasions because of my technical expertise and past career exploits." I moved my hand a little higher up her leg.

"Socially you will find that I am very outgoing and get along with everyone but can be a big flirt. I am comfortable anywhere from a black tie affair at an embassy to playing on the floor with preschoolers." I moved my hand even higher up her leg.

"Physically you will find that am very strong, extremely quick and have exceptional endurance. My real work requires those attributes." I, once again, moved my hand up her leg near the top of her thigh.

"Sexually, I am well endowed, as you may have already noticed, but I really know how to please a woman with many parts of my body and love to explore my partner's body, by gently but firmly teasing her erogenous zones. You have me very turned on," I said as I moved my hand up to her panty line.

"Romantically I seek to make a woman fell like she is queen of the world and love to kiss until our lips are numb." I gently readjusted my hand and softly stroked her mound. She was soaked.

"So now you know about me, please tell me about yourself."

Jeri: I was really sorry that I had worn such a tight skirt. It was making it very difficult for Roger to work his fingers high enough under the tightly stretched material to get where we both wanted them to be. I was unable to really open my legs for him, and the skirt was long enough that no matter how much I squirmed, it would not really work up very much.

We were still kissing passionately, and I dropped my hand on his lap and was able to feel a very sizeable bulge there. He seemed to be almost fully hard, and of a very impressive size indeed. I could feel my cunt give a little involuntary contraction as I ran my searching fingers over his cock. I pulled back slightly from his demanding mouth to draw in a deep breath, and noticed that several people were beginning to take notice of our activities.

I gave him another quick kiss and whispered, "Take me somewhere, I've got to get out of this dammed tight skirt! Shall we go to your room or mine? I don't care!"

We got up and hastily left the lounge, found an empty elevator and Roger said, "My room then." He grabbed me again and kissed me hard, his tongue probing deep and both hands rubbing my ass. I could feel his hardness against my body, and swayed back and forth to give him a little bit of stimulation. The elevator slowed and then stopped at his floor. We were walking down the hall toward his room, his hand still firmly clutching my ass cheek, when we rounded a corner and almost ran into an elderly couple. They gave us a dirty look as they passed.

We finally reached his room and as soon as the door closed, he was working to undo the buttons on my blouse. Suddenly, miraculously, the blouse was gone and he released my skimpy bra very quickly. He attacked my tits with his hands, and then his mouth, licking, kissing, sucking, biting lightly, and I held his head close, my nipples so hard that they were almost aching.

I reached down and began stroked his cock through his pants. I then went to my knees, unzipped him, fought my way through his underwear, and pulled that glorious cock out. It was long and thick, throbbing slightly, aching for my hungry mouth, which it soon received. I leaned forward, kissed my way up and down its impressive length, flicked a drop of delicious pre-cum off the tip and lowered my head. I took him as deeply as I could in one long slow motion, until I could feel the head at the back of my throat. I began a slow bobbing motion, deliberately moving my head up and down, tongue flicking at the underside, and trying to go a bit deeper each time. I did not really know if I could swallow him. I could swallow most cocks, but this was about as long as any I had ever seen, so was a real challenge for me.

I pulled back slightly and looked up at him. Our eyes met and I continued to look at him as I slowly went down again, further than ever before, and felt his freshly shaved pubic region press against my nose. The head of that delicious cock was firmly in my throat now, and I held it there, as deep as I could take him, until I had to pull back for air. I looked up at him again moaning and then I did it again, slower, deeper, and wishing I could keep this lovely cock in my hungry mouth forever.

I was moaning constantly, slobbering all over it, and eventually he pulled back, then helped me back onto my feet before pushing me down onto the bed. This was exactly where I wanted to be. He covered me with his body, kissing me passionately again, our tongues intertwining together. His hands stroked my throbbing tits. Working lower he stripped my tight skirt down my legs, then pulled my flimsy panties off. I could now spread my legs wide for his probing fingers. He began to work his magic on my core, stroking my clit. He then slid one eager finger into my clenching cunt. He added a second one and fingered me hard but not roughly. This was a man who obviously knew his way around a woman's body. I was self-lubricating freely now, my juices coating his fingers, and starting to run down my crack and over my asshole.

Roger: As I probed her with my fingers, I started kissing her breasts working my way around each but not yet touching her nipples. I licked my way around and around her breast and sucked pretty hard on the underside while lightly teasing the nipple of the other breast with the end of my index finger. As I spiraled my way upward, I came to her erect nipples with my lips. I then took her nipple into my mouth beginning with a gentle kiss and increasing pressure as I French kissed the nipple using my tongue to excite the very end of each nipple. I then began to suck on the intended target with greater and greater pressure while maintaining my tongue's assault on her nipple. After I finished with one, I gave equal time to the other while still exploring her honey pot with my fingers.

After finishing with both of her perfect breasts, I kissed my way down to her naval and began an equally intensive make out session with her tiny naval. Finally she said, "I want you in me!!!"

I looked up at her from my perch and smiling said, "Not yet."

I then eased my way down to her sweet pussy, extracted my fingers and began to lick her honey pot. Gently at first beginning with the outer folds of her pussy lips but then, with ever slightly increasing pressure, zeroed in on her love canal. When I got all the way to the center, I placed my entire mouth over her dripping sex and began to suck the juices from her. After a few minutes of pleasure, I then used my tongue to fuck her insides while grabbing the tops of her hips and pulling her more firmly onto my face.

I then used my tongue to trace a path from the bottom of her vagina to the top and then up to her sensitive clit. As I reached her erotic button, her wiggling became more intensive but I did not go directly for the most sensitive areas. Instead, I worked a slow tongue trace around the outside of her clit, enjoying the sensations and feeling all the parts underneath and around the surface and tip of her clit. When her breathing got more rapid, I used my tongue to massage the surface of her clit and placed my whole mouth over it. I then sucked harder and harder, drawing her whole clit into my mouth. Only then, and while maintaining suction, did I use the tip of my tongue to massage the very tip of her clit in a rapid, repeatable pattern. As her hips started to buck, I slid one finger into her waiting ass and my thumb into her precious pussy. At that point she went wild with a whole body orgasm, shaking uncontrollably and her juices coating my face and the bed.

After I finished bringing her to at least one orgasm, I backed up so that I could get a good look at her sexy body. I tried to take in every square inch of her naked form as she pulled me onto the bed. She then straddled me, reaching for my cock as I reached out to caress her tits. Guiding my shaft toward her pussy, she lowered herself onto it and we both moaned as I easily slipped into her. She paused briefly sitting on my cock as I caressed the soft, smooth flesh of her tits. We then slowly began to move up and down on it. Being as snug and as wet as she was, her pussy felt outstanding as she was slowly riding my cock. I was grateful that I had not come yet.

I was leaning back as she was riding my cock so that I could see her tits while I was fondling them. The harder and faster she rode me, the more they were bouncing so I ended up occasionally moving my hands around to caress her ass while watching them bounce. I kept bringing my hands back around to massage her tits and nipples some more. The more I watched them and fondled them, the more I wanted to lay my cock between them and caress them as I fucked them. I was thinking that I could likely hold out until she came again while riding me but that didn't happen. I came right away. I didn't have time to stop because she was obviously already building toward another orgasm. I was pushing up into her each time she dropped down, ensuring that she was getting as much penetration as possible. When she finally dropped down onto my cock and just sat there, it was only a moment later that she cried out as her entire body started shaking. It was another long and obviously intensely pleasurable orgasm during which I caressed her breasts.

I then rolled her over onto her back and began slowly making love to her gaining speed and momentum with each thrust. As I came closer to cumming for the second time, I could feel my eight and half inches growing the extra half an inch and pressing against her cervix. With a loud grunt, I emptied myself again into her womb.

She said, "That was amazing."

I simply smiled and said, "We are not done yet," as she looked at my still erect cock.

With gentle persuasion from me, she climbed off of my cock then positioned herself in front of me on her hands and knees. I got up onto my knees behind her. I ran my hands over her soft, smooth ass then gripped my cock and guided it back into her pussy from behind. We both moaned as I slid all the way in until my hips were pressing against her ass. Holding her hips, I began to slowly slide in and out of her, still relishing the snug, slippery feel of her pussy. It didn't take long to get a good rhythm going then I slipped my hands up from her hips to cup her swinging boobs. I'm not sure if fondling her tits actually made my cock even harder but it sure felt like it. She seemed to be moaning more and pushing back harder, though that could also have been due to my hands brushing over her hard nipples. I started pounding away with the intent of giving her the fucking of her life.

"You might want to try slipping a hand back," I said, while continuing to fuck her, "and caress your clit."

She reached under herself, started teasing her clit, and was quickly moaning even louder and pushing back harder. I matched her pace but was still fondling her luscious breasts as I was pushing my cock deeply into her. I was still a bit dumbfounded that we were naked and fucking in a hotel room. Her pussy was feeling even hotter and wetter the longer I was fucking her.

As she was pushing back harder, apparently getting close to her next orgasm, I reluctantly released her beautiful breasts and straightened up, taking her by the hips again and began driving harder and longer. I was pulling all but the last inch out and then slamming into her again and again. I was looking down at her ass, watching it jiggle as my hips tapped repeatedly against it, while feeling the lubrication in her snug pussy increasing even more. I expected that I'd be cumming inside her again.

When she finally gave a shove backwards and held herself there, I pushed my cock into her as deeply as I could, shoved two well lubricated fingers up her ass and a moment later, she let out a loud cry and started shaking. I slid in and out of her a few times as she surrendered to her orgasm, wanting to make sure that I enjoyed the additional flood of even more lubrication within her hot, wet pussy. It was another long and clearly intensely pleasurable orgasm for both of us as I came buckets inside her at the same time with the overflow squirting out from our union.

After she stopped shaking she rolled over onto her back and said, "That was amazing."

I just looked at her and said, "We are not done yet."

Jeri: This was turning out to be a really wonderful evening! I had enjoyed sucking Roger's delicious cock and then he had eaten me to a spine melting orgasm. He took me and fucked me better than anyone had for a very long time. I could tell that he was one of those men who really loved the taste of a woman's juices. Some men would not eat a cunt, some did only reluctantly, and some just dove in and enjoyed every second of it. Roger quite obviously was one of the latter. I would later find out that he would eat me even after cumming.