Inter-Generational Affair

Online dating is especially great for us married folks who need the secrecy. I had dabbled in online sexual activities for some years, including role and fantasy play, voice chat, and even cam to cam. This got boring after a while and I stopped hanging out in chat rooms and lost contact with my online girl friends. Besides these online infidelities, I have been very honest in my 16 yrs of marriage. About 6 months ago, I decided to give online dating another shot. My name is George, and this time I was looking for an in the flesh experience.

I was born and brought up in the US, and have lived in California all my life. I am a 40 year male of Indian origin (parents from India). I also have some (1/4) Portuguese blood in me from my dad's side. I am very well educated (doctorate) and work as a senior engineer. My job involves simulation and programming, and I am often working on the computer 5-7 hours a day.

I started hanging around in the "Interracial Dating" chat rooms of a popular web portal. There are normally about 100 chat rooms for interracial dating, with 10-50 users per room, mostly occupied by BOTS. I generally parked in one of the most popular rooms, while I worked on the same computer. I never listened to or watched the room conversation. I only chatted with ladies who messaged me, and who lived within about 150 miles of me.

After a few near misses in the first two months, I got lucky when Vicky messaged me about 4 months back. She started with 'I absolutely adore your profile picture. Where in cali are you located?'. Being fully aware of the powers of advertising, I had filled out my chat profile completely, including age, marital status and location as 'cali' to be discreet. I had also included a discreet faceless side view full body picture of myself in my black boxer briefs. This is the same profile picture on my literotica profile, but unlike my literotica profile picture, my chat profile picture was uncropped.

She seemed very enamored by my picture. I workout 5-6 times a week with various physical activities. I am often complimented that I have a better body than most 20 year olds. I am built like a middle weight boxer, with minimal body fat, and weigh in at about 5-11 , 170. I am very dark skin (think chocolate color) and have always been attracted to fair skin ladies.

Vicky turned out to be white, single, 20, still in school, and had just broke up with her latest lover. I re-emphasized my age and marital status, and she indicated that she was cool with it. She indicated that she had been with only 3 men before, but the last one she just broke up with was a married man in his late 30s. She also indicated that she had never been in an interracial relationship before, but that she fantasized about it everyday. She indicated that she was attracted to older fit men, but only those who were fully bald or had a full head of hair. I told her that I had most of my hair except for a tiny bald patch that was beginning to show at the crown, but was never noticeable from the front. She was satisfied with that.

Vicky lived about 70 miles away from me on the central California coast. This was perfect since there was a small town in between us. This meant it would only be about a 30 minute drive for each of us if we decided to meet. However, Vicky lived with her mother, who kept her on a tight lease. It was very difficult for Vicky to get 3-4 hours off during the week days to meet.

Over the next few weeks we chatted daily during the weekdays for 1-2 hours a day. In chatting with her, I understood why she could communicate and have good chemisty with men in their late 30s. She was extremely mature for her age, and rarely used the normal lingo that an average 20 year old girl uses. We exchanged body pictures which included nude faceless pictures of us in various poses. Vicky is very petite and attractive. She is about 5-1, 115 with nice 34C's and a lovely round firm butt. She was completely shaved down under which was an absolute turn on for me. She shyly admitted that she shaved just for the picture and would continue to do so for our meetings.

Now, I have a very secluded private office with a mike and headphones. Our online chats during the day included voice chats which were incredibly hot. One day I had to work from home. On that day we did a cam to cam chat. This ended with both of us in the nude, and mutually masturbating. I made sure to never let Vicky see my face and vice versa.

Our online affair went on for a few weeks, and I was beginning to get the sinking feeling that this was as far as Vicky wanted to go. However, I never pushed her to meet, and I was very understanding of her schedule, and the tight lease that her mom had on her.

Our first meeting

After weeks of online chat Vicky suddenly informed me on a Tuesday, that she would be available for most of that Thursday. Her mother was going to be traveling out of town on business starting early Thursday morning and returning on Friday afternoon. I could hardly contain myself or sleep that night.

We decided to meet at a Holiday Inn in the town between us, on Thursday morning around 10 AM. I would have to return by 4-5 PM. I decided to take the day off work on Thursday. Every couple of weeks, I normally take cycling trips on the California coast. These trips typically take 6-10 hours and cover 30-50 miles. Very often I drive out anywhere between 10-50 miles with my cycle atop my car to a cycling route. This turned out to be a perfect excuse at home for thursday.

I woke up early on thrusday morning, shaved, took a long shower, groomed myself completely, and drove to the town in between us. I parked one block away from the Holiday Inn at a large department superstore. It was about 10 AM. I picked up some massage oils, lubricants, and condoms. I put them in my laptop case, along with some cash and walked the full block to the holiday inn. I left my wallet and ID in my car. I was just being very careful not to reveal my identity or my car.

Vicky was already there outside the lobby of the holiday inn waiting for me. Seeing Vicky for the first time was one of the strangest, most exciting and most interesting moments of my life. Even though we never exchanged face pictures, we recognized each other immediately. She was dressed in a white t-shirt and a blue mid thigh length jeans skirt. She had brown eyes, brown hair with blonde highlights and looked absolutely adorable. I was dressed in blue shorts and t-shirt which emphasized my cycling butt and athletic build.

We hugged briefly. Then, I took her hand and walked her out to a private corner of the building. She seemed very comfortable with me holding her hand, so I felt confident that she liked what she saw. We talked for about 2 minutes before I pulled her to me and kissed her passionately. As we broke out of our kiss, I continued to hug and hold her closely. I told her that we should get a room and she agreed.

I had called the hotel the previous day. I confirmed that there were rooms available and that an early check in was allowed. I gave Vicky the cash for the room, since being married, I could not put the reservation on my credit card. We had agreed on this, while planning our escapade during our online chats. I waited outside the lobby for what seemed like an eternity before Vicky returned smiling with the room keys. I had asked her to get a Room with a King size bed.

We took the side stairwell and walked up to our room on the second floor. I took the key from Vicky, opened the door, and let her in. As soon as I let myself in and shut the door, I pulled her to me and kissed her again. My groin pressed against her abdomen and it took all of 30 seconds before she felt my raging erection pressed against her abdomen.

Oral Bliss

As we kissed passionately, I dropped my hands below her thigh length skirt and caressed her butt outside and around her panties. I then pulled down her panties to her knees, while still kissing her and continued to caress her bare butt. Vicky got out of her panties and in turn had unzipped my shorts and I let them drop to the floor. My penis was fully erect and straining to get out of my black boxer briefs.

During our chats Vicky indicated that she was fairly submissive and loved a man to take charge. She had indicated that the first thing she wanted to do was to taste me in her mouth. I was a bit concerned about this, since I did not want to spend my first shot right off the bat. During our chats, I had honestly reminded her that I was 40, and that I have never cum more than 2 times within the span of a few hours, especially in the last 10 years. She was cool with that and assured me that she would make me cum 3 or more times.

I pulled Vicky away from our kiss and had her kneel about 12 inches in front of my boxer briefs which was her fantasy. She was still fully dressed except for her panties. I then pulled my erect penis and testicles through the opening in my briefs. Vicky gasped as she looked at my Uncircumcised penis up close and personal. She had seen pictures of it and the fact that she had never been with an uncircumcised man before turned her on a lot. I am about 7 inches long (Yes I have measured it exactly) and very thick, though I have a fairly pronounced curve to the left. Being uncircumcised tends to add thickness on the head of the penis. I pulled Vicky's head towards my penis and asked her to lick it gently. There was precum oozing out of my penis and she delicately licked it up with her tongue.

I gently caressed her hair and then firmly but gently held her head still and told her to open her mouth. I pushed my penis all the way in till she gagged a bit and then pulled it out till the tip of the penis. I then moved in and out of her mouth slowly, both by moving her head back and forth and moving my hips back and forth. She had her lips adjusted so that I could face fuck her as we had discussed numerous times in our chat sessions. I also asked her to play with my testicles which she readily obliged. I must admit that I rarely ejaculate quickly because I do my kegels very regularly and have fairly good control over my ejaculation. However, seeing Vicky down there with her beautiful mouth over my penis was just too much. After just a couple of minutes, I felt that I was getting close to ejaculating, so I pulled out of her mouth to avoid losing my first load so quickly.

While she stared at my penis up close I pulled the foreskin back over the head. My foreskin is relatively tight even though I pull it back and clean it daily. When I am fully erect, and pull the foreskin back, the foreskin tends to tighten like a noose around the base of the head of my penis. This has an added effect of preventing me from ejaculating too quickly. Vicky had seen pictures of my penis fully erect with its forekin pull back, just as it appeared in front of her. I asked Vicky to lick my uncovered head and she did so very gently. I then started to face fuck her again. Now, I could increase the intensity and speed while moving in and out without fear of ejaculating too soon. Every now and then I pulled out of her mouth and gently slapped her face with my penis and gently moved my penis tip against her cheeks, nose and forehead. In our chats, she said this was something she absolutely loved. I like this too since this gave me a break from face fucking her, and prevented me from ejaculating too soon. After slapping and moving my penis against her cheeks, I would get back to face fucking her.

After minutes of the greatest pleasure filled moments of my life, I was ready to ejaculate and warned her that I was. I pulled out just outside her lips and told her to open up wide as I squirted into her mouth. As soon as I had finished, I could see her tasting my cum and swallowing it. At the same time I gently pulled her head forward and asked her to lick the cum that was dripping from my penis. She did so very readily.

I was spent already and started to wonder If I would ever be able to get it up again for the rest of our session today. I gently pulled her up to me and kissed her passionately again, thanking her for the wonderful experience. I then reminded her that it was now my turn to take care of her with a full body sensual massage which was her fantasy.

Sensual Massage

After the perfect oral performance Vicky bestowed upon me, I was very determined to repay her the best I could. She told me that in the last few weeks, she had regularly fantasized about my brown muscled body rubbing against her delicate white skin while I provided her with a full body sensual massage. I tucked in my penis, which was hanging out through my briefs, and took of my t-shirt off. I sat her down on the king size bed and helped her out of her t-shirt and bra. Her breasts were absolutely perfect (34Cs) with small perky nipples. I gasped as they came into view and had to stop myself from devouring them immediately.

I then laid Vicky on the bed, unzipped her skirt and slowly pulled it off her legs. Her pussy was absolutely gorgeous and completely shaved just like it was in her pictures. I turned her over so that she was lying on her stomach with her feet hanging off the bed, and got ready to give her a much deserved massage. I could not help but gawk at her nice round butt, which was the product of years of dance classes. We made idle chat while I got the massage oils ready and I turned on the heat since she was naked.

Now, to be honest I am no expert in the art of sensual massage. However, I had read and reread many articles on sensual massage techniques on the literotica site itself. I had visually practiced massaging Vicky numerous times in the last few weeks. Additionally, I carefully studied numerous sensual massage videos on popular video sites online.

I straddled her with my legs on either side of her and my groin located just behind the level of her butt. I gently applied the massage oil, and started with her neck and shoulders using my fingers, thumbs and palms to knead the stress off the shoulders. I asked her to give me feedback on the amount of pressure that she preferred, which she did. I then massaged her arms all the way to the fingers. I surrounded each of her fingers with my thumb, index, and middle finger, and I moved them up and down her fingers, one at a time.

I then moved to her back and massaged her from the backbone out to her sides using both hands at the same time, rubbing the oil into her back till it seemed to magically vanish away. I continued this for a while till I reached the top of her butt. Every now and then she would moan softly in approval, obviously enjoying the therapeutic massage.

After reaching the top of her butt, I got off from straddling Vicky's lower butt and walked to the back of the bed. I then started to massage her feet paying great attention to her toes which she absolutely enjoyed. I then continued up her legs massaging her calves in long upward strokes, one leg at a time with both my hands on each leg. After I was done with her calves I started to work on her thighs. Instinctively, Vicky spread her legs perhaps inviting me to massage her insides. This started to excite me and I started to feel myself grow under my briefs.

I obliged by placing a knee on the bed in between Vicky's calves getting into position to massage her thighs better. I used both hands on her right thigh moving outwards from the center. When I reached her upper thigh just below her butt Vicky spread her legs even more invitingly. I casually ignored this sign and went about massaging her thigh. I teased her during the the downward strokes by brushing the fingers of my left hand against her pussy. I then repeated the same process on her left thigh.

By now Vicky was completely wet and I was really proud of myself. I started massaging her butt. I dripped a liberal amount of oil on them and started massaging the right butt cheek first just like I did to her thighs. With every stroke my left hand would wander and linger near her starfish. She moaned in pleasure but I did sense some nervous tension in her. I knew she had never experienced any anal play before. I did the same to her left butt. Then I used both hands as I massaged both cheeks simultaneously starting from her butt crack towards the outside which exposed her starfish during the entire outward stroke. Vicky moaned in pleasure as I moved my mouth closer to her butt and gently blew onto her starfish and pussy during the outward strokes. She was dripping wet and I had to resist the urge to finger her pussy.

I got off Vicky, went to the bathroom, got a cloth moistened with warm water, and wiped off some of the oil from her. Then I told her to turn around to lie on her back. I still had my boxer briefs on and straddled her tummy with my knees on the bed around the level of her breasts. I massaged her scalp first, then her forehead, face, nose and chin all the while looking directly into her eyes. Then I moved my position to started massaging her chest area without touching her breasts. I then moved lower on the bed to massage her abdomen stopping slightly above her mound.

She was dripping wet as I massaged the front of her thighs, one at a time. I teased her by brushing across her pussy as I massaged her thighs. She responded with soft moans. I then finished the supposed therapeutic part of the massage with the front of her lower legs.

I then deliberately stood walked to the side of the bed next to her eye level and dropped my boxer briefs letting her know that the sensual part of the massage was at hand. I started massaging her around 10:30 and it was 11:15 now. Seeing her wet pussy and her lovely breasts had got me aroused again and I was as hard as I could get.

I climbed onto the bed and spread her legs and brought her knee up so that her feet were on the bed. I knelt between her legs so that the shaft of my penis rested against her pussy lips and started to massage her breasts. I rubbed oil all around her nipples and massaged both breasts simultaneously using my fingers and palms without touching her nipples. I varied the motions around her breasts sometimes even using both hands on each breast. Vicky moaned in pleasure as I massaged her breast for around 5 minutes. I then teased and played with her nipples using my thumb, index and middle fingers. She cooed and softly said that she loved what I was doing. I could feel the wetness between her pussy lips on the shaft of my penis.

I got off Vicky, took a pillow and placed it under her head so she was propped up. I placed another pillow under her butt so that she had a clear view of her mound. I moved back down the bed and knelt in front of her to massage her pussy. I poured a small amount of massage oil on her mound till it dripped down her outer lips. I gently massaged her mound and outer lips.

I gently squeezed the outer lip between my thumb and index fingers, and slid them up and down the entire length of each lip. I repeated the same to the inner lips of her vagina. I asked Vicky if my pressure or speed, was ok. She softly moaned that it was great.

I then stroked her clitoris with clockwise and counter-clockwise circles using my index finger. Intermittently, I would gently squeeze her clitoris between my thumb and index fingers. Vicky was getting very excited and I asked her to relax and breathe.

Slowly I inserted my right middle finger into Vicky's vagina. Very gently I explored and massaged the inside of her vagina feeling up, down and sideways. I varied the depth, speed and pressure. Then, with my palm facing up, I moved my middle finger back towards my palm to massage her g-spot. I varied the pressure, speed and also moved my finger from side to side, back and forth, and in circles. After a few minutes I also inserted my right ring finger in and continued the g-spot massage.