First Meeting and Cheating

I'm a dirty old married man, in my early sixties. I admit, I have been cheating since shortly after I got married, normally when I have been traveling. Not constantly, as there have been sometimes as much as ten years between me meeting up with another woman. Then I would meet up with maybe a half dozen women over a three to five year period.

About a year ago, I met online a beautiful, wide eyed brunette who lives in the city that I travel for consulting work about three to six times a year. Her name is Anne. She is rather straight-forward, saying she is looking for a hookup because she loves sex and she wants to achieve great orgasms. I really like women who know what they want, and that is exactly the kind of woman I like.

Anne and I continued to chat over the next couple months, and we both began to anticipate meeting when I am next in her city.

Well I am about 5-10, 210 pounds, somewhat good looking, retired military. Anne appears from her pictures to be about 5-2 with large breasts, a cute butt, sexy legs. She has shared videos of her oral talents, one with another guy and many with several of her favorite dildos. She likes to be on top too, and loves anal. She is between 25 and 35 years old, and runs half marathons every couple of months.

In September, a last minute opportunity to do some consulting allowed me to overnight in the city and then fly out the next morning to the organization's town. I found out about this about ten days before I would go. So during those ten days, I contacted Anne and she agreed to meet me at my hotel after I arrived.

I've arranged to fly in mid-day on Sunday, and I will not have to meet with my client I am consulting with until 11 am on Monday, in the hotel I will be staying at. As the plane lands, I turn my cell phone off airplane mode and text Anne that I have arrived at her airport. I get off the plane, and walk to the ground transportation area to catch a cab to my hotel.

In about an hour, I have checked into my room and texted Anne my room number. Since both of us have dealt with no-shows for hookups before, Anne wanted to make sure I was for real or did not chicken out.

She called my room, and I answered. We talked for a few minutes. She would arrive at the hotel in less than an hour.

I decide to shave and take a shower, given the smokers I sat near on the plane. I'm clean shaven, but I did this so that my chin and face would be as smooth as possible when I get between Anne's lovely legs.

Anne and I decided to first meet downstairs in the hotel lobby, then go over to the nice Italian restaurant in the hotel to get really acquainted. After dinner, if we both want to, we would go up to my room.

I sat in the large hotel lobby, facing the entrance way so I would see Anne walk in. Yes, I admitted I was a little nervous, partly because maybe she would not appear, partly because I was so attracted to her mind and body. I sat there with my phone in hand, just in case she sends me a text saying she is not coming.

I waited patiently, and then she steps into the hotel wearing a cute blue skirt with a rose colored blouse that accented her breasts. Her skirt stopped about eight inches above her knees. She wore short heeled shoes, and I could see a runner's well developed ankles. I was getting hard sitting there before I started to get up from my seat.

Anne looked around, and quickly spotted me starting to stand and walk to her. I said, "Anne."

She called me "George."

I reached for her right hand, as if to shake it, but she quickly just hugged me and I hugged her back, tightly.

I noticed a couple standing nearby, both looking at us, maybe wondering about an old man meeting up with an attractive younger woman, so I winged it by saying loudly, "It's been a long-time since I've seen my favorite niece, how's your mom and dad doing?"

Anne immediately looked at me, a bit puzzled, but I have found she has a quick wit and is a really intelligent woman, she quickly replied, "Well mom's still mad at you for drinking all her good wine at Christmas and your brother, my father, said to make sure you buy me dinner."

I replied, "Well they have a lovely Italian place here, so let's go over there, my treat."

We both laughed, I glanced over at the couple as I crooked my elbow and offered it to Anne in order to escort her to the restaurant. The nosy couple quickly turned away.

"What was that about?" Anne asked as we walked through the lobby.

"Just someone watching us, maybe wondering why a young beautiful young woman was meeting with an ugly old man like myself."

We walked through the door of the restaurant and the woman took us to a table in one corner of the room, one that typically seated four, with a cushioned bench and two chairs. Anne sat down on the bench, and I sat next to her on her left, and we could both look out on the other tables.

We were given those big fancy restaurant menus, and Anne ordered a glass of white wine while I asked for a diet Coke. While we were looking at the menu, my hand reached over and touched her knee. Surprisingly, I felt that I might give her a static shock, because the restaurant's carpet was rather thick.

Anne smiled and breathed a little moan.

As expected, we both were not very hungry and could not decide on any of the entrees. Since it was nearing two o'clock, I suggested we could have an appetizer now and could either come down later or order room service in three or four hours.

Anne took me up on that idea, and she choose a chicken quesadilla dish.

I laughed, and told Anne that I loved Mexican food.

I massaged her lower thigh for a few minutes, then moved my hand to her shoulder and down her left arm. Slowly. Moving back up to her shoulder, I rubbed her neck, and then massaged the back of her scalp. Her hair felt so silky.

I looked around the restaurant, and there were not that many people sitting at the tables. I did notice one older couple looking at us, though not the two from the hotel lobby. The woman appeared to be particularly looking our way more often than her male companion.

I leaned over and whispered this information into Anne's ear, and she laughed.

Anne whispered back that maybe they were just voyeurs and we should put on a show.

I looked down and noticed that the table covering went down about two inches from the top of our table. While my hand on Anne's thigh could be seen from our female observer, she might be able to see my hand as it moved closer to Anne's crotch. Which was what I started doing as I was whispering to Anne.

Anne responded by opening her thighs up a little to provide me access, and it appeared the woman received a lovely view too. I moved slowly, and had reached a spot where I expected to find her panties.

To my surprise, there were no panties, just the wetness of Anne's bald pussy lips. I rubbed my fingers up and down slowly along her labia.

Anne moaned a little, encouraging me to continue exploring her. My observer was watching, and I swear she put her hands down to her lap, under her own napkin, and they were moving too.

I had probably spent only a few minutes rubbing Anne when the waitress brought our appetizer and sat it between us on the table. My right hand was under Anne's skirt. Though I am right-handed, I can eat with my left, and after Anne took a triangle, I took mine while my right fingers continued to caress Anne's lovely petals.

Our food was a little sloppy, and I fumbled for my napkin, which was in my lap, so I pulled out my right hand to catch it. Anne watched as I pulled the napkin up to my mouth, and carefully put my two fingers from my right hand to my lips. I told her she tasted good. I looked out to our neighbor, who was licking one and then two fingers.

We continued to eat, with my right hand returning to its exploration mission down Anne's thighs. I then felt Anne's hand go under my napkin, and gently squeeze my penis. I became quite hard immediately. My other response was to rub Anne's clitoris with my thumb while I had two fingers moving in and out of her pussy.

At this point, I noticed that Anne had a food particle just outside her lip, and given that both of her hands were busy, I grabbed my napkin with my left hand, turned my body, and gently wiped her face.

As I moved away from her face, I moved my hand downwards, and felt her left breast and nipple, softly, while the napkin camouflaged my movements on her tit. I looked over to our female observer, who smiled and actually gave me a thumbs up.

Anne and I continued to play until our food was gone, and our waitress asked if there was anything else she could do for us. I asked Anne if she wanted anything else.

Anne shook her head no, not wanting any more food. But she was hungry for something else.

I asked for the check, and the waitress went to go prepare it. I whispered to Anne that we maybe I ought to give the waitress my room number and an invitation on the check, as she had to suspect what we had been doing sitting and playing under the table, and perhaps she might join us after her shift.

Anne just smiled thinking about that fantasy.

The waitress returned with the check, and I added the tip with my room number and signature. I did write a note to join us after her shift if she wanted to.

I then turned to Anne and asked her if she felt comfortable about coming upstairs.

She agreed, and I got up, offered my hand and helped her stand, and we moved towards the exit of the restaurant and started walking in the hotel lobby to the elevators. That's when I noticed the large purse that Anne was carrying.

The elevator door opened to us, and we stepped in with no one there. I immediately leaned down to kiss Anne, and we enjoyed a long, French kiss until we heard the bell ring, signaling that the elevator was stopping at a floor.

We were on our floor, and I escorted Anne down the hallway to the entrance of my room. I used the electronic card, and the lock clicked with a green light, and I opened the door so that Anne could walk in.

It was your typical suite hotel room, with a large bathroom immediately on our left, a closet on the right, and then opening up into a small living area containing a sofa and one chair, with the king's sized bed beyond and next to the windows. I had opened the heavy curtains earlier but had the lighter curtains closed to prevent anyone from outside of looking into the room, as there were several tall buildings nearby.

Anne turned to me, and immediately began kissing me again. I wrapped both of my arms around her initially, with her hands going to my shoulder and chest, rubbing my hard nipples. We kissed for quite a while, paused a little looking in each other's eyes, and kissed again.

"I'm really horny," said Anne.

"I am too," in reply.

We both began to take our clothes off, and helped the other take theirs off too. In seconds, we were both down to our underwear, me wearing tidy whiteys and Anne just her silky bra. She pushed my underwear down past my knees while I was playing with her bra, and I kicked them off. She turned around, and I was able to unhook it on my first try. I actually reached down to her clothes on the floor, picked them up, and put them on the sofa. My clothes I left on the floor.

I knew that Anne wanted to get to her knees on the floor and taste my cock. As she started to go down, I lifted her up, and directed her slowly to the bed, having her lie there with her knees bending at the side edge of the bed. I went to my knees on the floor, which gave me a spectacular view of what my fingers had been exploring in the restaurant.

I told her I knew she wanted to go first, but I was going to lick, kiss, and suck her first and she was just going to lie there on the bed and take it like the slut she sometimes was.

I started off with my lips on the inside of her left thigh just above her knee, while each hand was massaging a calf of her lower legs. Very slowly, I moved upwards, towards where her legs converged. Not in a hurry, I could smell her desire, building. Halfway along my journey up her left thigh, and straining my arms massaging her calves, I stopped, and moved back to behind her knee on her right thigh.

I think this caused a little frustration on Anne's part, I thought I heard her say something like "not fair." I then repeated myself up her right thigh, continuing to massage her lower legs.

I reached the point where if I were to continue in my journey, I could no longer rub her calves properly, so my hands moved to both her thighs, rubbing both inside and outside both of them. By this time, I was several inches from my major objective. I looked up and saw how her lips were wet, and then I looked up more and saw that Anne had reached for a couple pillows and put them under her head, and was watching my explorations of her body.

Before she knew it, my awesome tongue had hit pay dirt, as I licked through her lips to her clitoris, and downwards until I circled around her rosebud. Repeating this several times, only stopping at the both the top and bottom, I finally settled to tonguing inside her pussy, while a finger began playing with her clit. I was listening, as every woman is a little different in their geography and what she liked where, with different pressures, tongue or fingers, or even my nose was involved as some point.

To my satisfaction, Anne began to tense up, and I knew what I was doing was working. She definitely was having what I call small, micro orgasms. I licked down to her anus, and quickly tongued fucked her there. This got another round of small climaxes.

I returned back to her cunt, and continued to play with her clit and fucked her with my tongue and fingers. Anne grasped, and said she was going to cum, really hard.

She did, with her thighs locking around my head into a vice like grip, and my face got wetter, and I clearly tasted a slightly different flavor, the results of her squirting while she climaxed. She tasted really good.

I found out quickly that after a good climax, she was rather sensitive down there, and she pulled my head out and upwards to her mouth. We kissed and she licked my face that was wet with her own juices.

I kept hearing "oh my god" in between kissing, and recalled I also heard her say that several times when I was between her legs. But I was busy then, and like any guy, was not paying attention to what she was saying.

I then nudged her to turn on to her stomach, and lying to her left side, began a back, neck, butt, and leg massage. Now her being a physical trainer, she is no doubt much better at giving massages. But I try, and no one complains about them. I looked at the clock on the bedside table, it was now past 4:30. I had spent almost ninety minutes between Anne's lovely legs.

After the massage, she pushed me on to my back in order to give her access to my cock, which was not that hard. She licked its top, and began to suck. She gave a great blow job, completely taking me into her mouth down to my pubic hair.

I was very hard in a few minutes, and then she rolled on top of me, impaling my penis into her pussy. She started out in a cowgirl style, with her sitting on my hips and going up and down, allowing me to play with her breasts and touch and pinch her nipples. I found that every time I pinched or pulled her nips, her pussy contracted and squeezed my dick. I was getting close, and told her.

Anne laid down on my chest and told me to cum inside her. I started to thrust upwards, and she continued to squeeze me, while my hand massaged her tits. In a few minutes, this dirty old man came inside her. I do not think she came, though I do think she had those micro orgasms again. I asked her later, and she told me she had been rolling since she began to suck me.

She laid there on top of me for several minutes, then rolled off. I then moved very quickly and my face began to lick the outside and inside of her pussy. Anne screamed when she figured out what I was doing, saying no man had ever ate a cream pie out of her. I licked and sucked her dry.

I crawled up to her face, and kissed her, letting her taste tasting her and my juices. She then reached for the blankets, and pulled them over us. We probably slept for about an hour.

I woke up, it was now dark in the room, as I had not turned on any lights before because I had the lighter curtains opened and they let in the sunlight. I could see the lights of the city, and was looking at Anne's sleeping face and sexy body lying under the covers. I began massaging her silky long black hair and her scalp, and her eyes then opened, with a big smile on her face. We kissed again.

We both decided that we would each take a shower, though Anne first went into the bathroom, grabbing her large purse, and closed the door. Now me being married for four decades, I was used to that.

Then the door opened suddenly, and Anne told me to get my butt into the shower.

I got into the large shower, and soon Anne was on her knees giving me another blow job. I was enjoying it, but I was not getting hard. She said she expected I needed more recovery time, but she came prepared.

She had already lubed up a dildo, and she asked me to do the honors, in her ass. I got down on my knees, with my mouth licking her pussy and clit, and began to move the dildo in and out of her rosebud. In only a few minutes, she had another climax that caused her to kneel down in the shower stall.

I raised myself a little, with my soft cock at the level of her big tits. She grabbed my member, and was rubbing it on and between her breasts. This was getting me a bit hard.

Anne immediately stood up, turned around from me, leaned against the wall, and told me to do her doggy style in either hole.

I held my dick in hand and pressed against her, and my head started to enter her asshole. The tightness caused me to get harder, and I went in to her several inches slowly.

She pushed back, and soon we were fucking quite hard. She tensed, and had another climax. I told her if I came again, I might be done for the night, and she let me pull out. We then soaped and rinsed off, and dried each other's bodies with the fluffy towels.

We came out of the bathroom, and decided we were now hungry for food. We got our clothes back on, and proceeded out of the room to the elevators. We decided to go to the steak place at the other end of the hotel.

Unfortunately, we were sat at a small table with two seats facing each other, so we could not play. Anne ordered a filet, while I ordered a ribeye.

This actually gave us a chance to talk, with us sharing our sexual adventures and history, and what we really liked and what we did not like to do. We had done that online through texting, but it was much more informative.

By now, it was nearing 9 pm, and we had a choice to go dancing at the small hotel club or go back to our room. Anne wanted to go back upstairs.

We both got undressed, this time not in a hurry, hanging up our clothes in the closet. I began with Anne lying on her stomach and giving her another massage, with her giving me some pointers and following her advice.

I then got between her legs and spent more than an hour eating her pussy and having her climax three times. At this point, she crawled on top of me, rubbed my cock on her wet pussy getting me hard from just watching that, and she proceed to fuck me cowgirl, then reverse cowgirl, and finally we ended it with me coming inside of her in the missionary position with her legs wrapped over my shoulders.

It was nearing midnight, and we decided we needed to sleep. We then got ready for bed, me taking my night time medications, her doing whatever women do in the bathroom for half an hour, and laid in each other's arms and fell asleep.

Anne had decided to take off work on Monday, so we had until about 10 am to sleep and play before I had to take a shower and get dressed for my 11 am appointment at the hotel.