[FM] The fat nerd, and the sexy barmaid

We are speaking of about 20 years ago, I was a straight, single, obese, bearded nerd with low/middle income, living with my divorced mother in a small flat in the town center afflicted with a powerful sex drive, but very few occasions to put it in practice. At the time me and my group of friends, a mixed bag of couples and singles of both sexes, were loyal patrons of a at the time popular cocktail bar: we gravitated there after work on Friday evenings, started to drink – my poison of choice was the Martini cocktail – smoke and chat until everyone was starved, then we went for a pizza or some low cost trattoria, then everyone for himself: couples, I presume, at home to fuck, we singles around alone to find someone to fuck with, or in group drinking and talking into the early morning. Standard provincial life.

[MFF] Greek massage for two

This story is from the days when me [M46 at the time] and my wife [36 at the time] were not married, and used to travel three or four weeks per summer with rucksacks in our backs. I am, and was, 184cm, muscled but chubby, dark blond, beard, smallish cock, she is 175cm, light brown hair, fit, small very nice tits, great, and I stress great, ass. That year we were travelling in Greece, after a tour of the Peloponnesus by car we visited a couple of islands, one almost devoid of tourism in the northern Aegean, then a smaller one in the Cyclades that is a classy tourist destination.

The sexual tension was high as it can be, i.e. we were fucking like rabbits every night, and sometimes during the day, with an interesting episode in a small public beach that I maybe will tell you in another story. In our last Island, the classy one, we rented a room near the port village, and a moped and we changed beach once or twice a day.

The first time I fucked my girlfriend, now wife, in the ass [FM]

A bit of background: we are a stable couple of 7 years with one son, me [M52] quite tall, a bit on the chubby side, average/smallish cock, she [F42] 10cm less than me, fit, very nice smallish boobs, great, and I mean it, ass. This story is from 7 years ago, in the first months of our relationship, we were not living together, not even in the same town. I was visiting her for the weekend.

It was a Sunday early afternoon, after lunch, and she told me that she had an itch in her butthole, a real itch not a “I want to be fucked itch”, so she asked me to help her put some ointment, actually shea butter. At the time we had sex like rabbits when we were in the same city, but we had not tried anal sex together, not even discussed it if I remember well. I touched her anus during reverse cowgirl, she showed to like it, but nothing more. Anyway I told her “OK, I’ll help you”. She went in the bedroom, laid prone on the bed, without shorts or knickers, but with bra and a t-shirt, legs a bit spread. I was kneeing beside her and happily complied starting to massage her anus, which actually was a little red, with the sha butter. After some minutes I felt that she was liking it, and I began to think about a possible pleasurable evolution of the massage. I continued and I noticed that her vulva was a bit swollen, so I started to massage more deeply, I inserted a finger.