I started on my journey to happiness a few years ago when I turned 49 and realized that my life was probably more than half over. My husband and I had become empty nesters after our son and daughter went off and graduated from college and found jobs so they finally moved out of the house. My husband made a six figure salary, so I did not need to work, though I did spend a few days a week down at the shelter cooking meals.
One day, one of those reality TV talk shows did one about women with an obsession, the desire to find men that were very, very endowed. At first, I giggled at the remarks and explanations that I heard from the women. How could they cheat on their husbands or boyfriends to get someone like that? Anyway, I enjoyed the show and went off to do the laundry or something.
Afterwards, as described in the previous story, I began my journey looking for that big, hard cock. I tried to meet & greet with three men who responded to my online add, meeting only with two of them. I decided based upon that experience to better screen them in the future.
Meanwhile, my husband with his five inch cock knew how to use it just right on my pussy, clit and in my ass after he came back after almost two weeks in China. And after a week of that, I changed up a little by meeting my best friend Meg when her husband went to a Celtics game on Sunday afternoon.
During the day, I would log on to AFF and check my in-box. Most of the emails were vulgar and clearly they could not even read my tagline, which said LOOKING FOR CAMBRIDGE MASS AREA 8+ MARRIED COCK ONLY!!! I mean, did that guy in Los Angeles really expect me to travel out there to suck his cock? So generally, there were only two or three emails a day that I bothered to open up their profile. I did pay for a subscription that allowed non-paying users to send me emails, opening to find that nugget of a cock that was married and did not have the money to spend for a subscription. After all, I was looking for someone with the right equipment, decent looking, a nice personality and good grooming habits, not someone who I wanted to fall in love with.
This step seemed to open up a few more candidates, as my profile and headline indicated that they could send emails to me. It also doubled the number of emails, again, most of which were either vulgar, not married, not from the Boston area, etc.
For those that seemed promising, I would reply to them via email, having decided to take my time and correspond for a few weeks, taking my time. It was unlike my first experiences; when I selected three guys and scheduled meetings with them. So I had about a dozen guys I was corresponding with, some of whom did not respond everyday (which made sense to me, if they were really married and doing this in secret). I created folders for each of them, and about once a week, I realized I would have to "catch and release" a few of them who did not sound right, or wanted something that I was not looking for.
I had used the friend feature on these dozen guys, so once in a while I would see them online. That gave me an opportunity to chat with them in real time. It also led to some of them being voted off the island.
Most of them kept asking to meet, at least in some public place to get to know each other better. They also wanted to exchange photos, but I decided to go with about ten pictures on my profile that showed off my body, and showed a shot of my head and hair without revealing my face. There was a Playboy-style shots of my ass, pussy, legs and tits that my lover Meg had taken on Sunday afternoon. So I figured I had given them enough information about myself, without putting myself at risk to the general public. I was mainly interested in seeing a well endowed individual, and then moving on from that.
It did get me thinking about how we would get together and what time that might be. For me, with husband traveling twenty days a month, I had complete freedom to plan for such activity. I could even invite Meg as an escort on a Sunday afternoon if need by. I had decided that I would probably not meet them at my apartment, what if things went bad, or if the affair ends, would I really want them to know where I lived? Also, I was calling myself Diane on my profile, to further protect myself. I decided that one of those small hotels near the Harvard campus would be the best place to meet, something that I could afford if the guy could not swing that.
I also realized that I was usually logging on during mid-morning, and I was probably focusing on the guys who worked second or third shifts, and were home and should be sleeping, while their wives were out working. So I made it a point to log in at different times during the day and evening, to provide more opportunities to chat with someone of them, which provided a lot of information on them and me quickly.
During my once a week review of candidates, I began to consider meeting a couple of them for a meet & greet and see if their reality matched their computer personality. The pushy guys were already close to elimination, I was attracted to those who were in it for the long term. So not wanting to be a tease, I suggested to five of them my desire to meet at some coffee shop in the next week, suggesting a Wednesday while hubby was off to Dallas. Three of them clearly could not make that day, and one offered an alternative on Thursday afternoon. So I scheduled meets for three of them for the next week.
Meg and I met Sunday afternoon at my apartment, and she spent most of the time reading the three profiles while I pinched her nipples and finger fucked her lovely pussy. She also looked at the other two candidates who could not meet on Wednesday, and actually thought one of them was the one I needed to fuck. I promised I would contact him for a meet later. I then pulled Meg to my daybed, and ate her out as she fantasized about me meeting one of the three this week, and quickly dragging them off to a hotel room for an afternoon fuck.
Meg was quite satisfied when she got dressed. She kissed me and wished me luck on my mid-week adventures.
I was going to meet Dan at 10 am at one coffee shop in Cambridge. I chose Cambridge because it was easy to get to from my apartment, but far enough away that lessened the chance of me meeting someone I knew, or more important, knew my husband. I was less nervous than the first time I had done this, getting to the coffee shop about five minutes before the appointment, and got myself a drink and was looking for a quiet spot to sit when Dan walked up to me and introduced himself.
Dan and I moved over to a booth, and he sat across from me and we leaned our heads forward so that we could not be overheard, but more so because the place was very noisy. Dan is a charmer, putting me at ease quickly, and I was laughing at his humor. I had seen his pictures, and if they are of him, he clearly was in the ten inch class. Dan had been married seven years to his college sweetheart, and they had two boys aged two and four. His wife had continued working after having the oldest, but after the second one was born, they decided she should stay at home, as the cost of daycare exceeded what she could be making. Dan managed the Asian financial desk at his company, so he worked evenings until 3 am, and it gave him lower six-figure income that they lived comfortably in a northern Boston suburb.
With his wife staying with the kids all the time, plus his job, led to a severe reduction in his sex life and led him to search for online adventures. It also turned out his wife had had some medical complications due to a third pregnancy after the second boy, and they had lost a girl after five months. His wife had been a bit depressed, which they had worked through, and clearly was not interested in getting pregnant again.
Dan had considered prostitutes but felt he could not handle the risk of disease or being arrested. He really did not make enough money to use escort services. He had moved here to go to college, and most of his friends were first his wife's. So he was interested, seemed to be a nice guy and we did seem to get along. I thought about inviting him to a local hotel, but Dan said he had worked late this morning because he had a dentist appointment this morning at 8 am, and had to get home to not raise any suspicions with his wife.
I wanted to physically check him out, so I suggested we head for the restrooms to do a quick grope session just to confirm and verify his ten inches. The restrooms were in the back through a narrow hallway, and I went to mine and it was locked. Dan looked in the men's room and discovered it was just a small room with a toilet, urinal and sink, so we both slipped in there and locked the door.
Dan quickly pulled me to him and kissed me, a very nice one that began exploring and ended in a nice French-style with our tongues twirling in each mouth. I could feel him get hard as he moved his leg to between my thighs. I kissed him again, and my hand reached down to check the equipment. Dan's cock was pointing upwards and it clearly was long and wide. I stopped kissing him, and asked him if he would like a complementary blow job to go with his validating his parking ticket.