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  • — Sex Confessions —
    Straight Male / 30

    I see the condo maintenance woman almost on a daily basis and we have grown friendly to the point where we trade off baked goods and other culinary items. I don't know her actual age but I have told her mine and she remarked that her 2 sons are almost the same age as I am so I assume she is 55-58 years of age. I'm not going to lie and say she is a 10 out of 10 but Janice when younger was likely a 7.5/10. She looks as though he has had a rough life and is divorced from her first husband and has lived with her current boyfriend for the last 6 years. One of my friends saw her one time in the lobby while she was cleaning and remarked that she looked like an old stripper. She has huge breasts which she is always self conscience of as whenever I see her working she attempts to hide them by crossing her arms while we chat. I would say she is about 5' 3" with a small frame which all the more accentuates her massive tits. Apparently they are "factory" equipment as she had told my girlfriend on one occasion about how they are a curse and she would like to get a reduction performed.

    At Christmas we offered to help set up the Christmas tree as the GF, MIL (she lives with us and my GF is a mirror image of her) and Janice are all under 5' 6" so I was tasked the job of placing the star and anything else beyond their reach. It was nice to see 3 sets of tits swaying while they bent down and especially Janice who was wearing a light t-shirt with no bra but with a loose fitting half zippered hoodie. Many times I thought I was going to be caught staring at them as I wondered what it would be like to tit fuck her and blow my load on them and her face. I was hard the entire time and was wearing these thin shorts which did little to contain or obscure the outline of my rigid cock. Several times I intentionally stood right in front of her face and the MIL while reaching to the top of the tree and I caught them scoping out my cock each time. They both grinned and I smiled back at them each time.

    Our condo happens to adjoin Janice on the 17th floor and our terrace areas are separated by a glass tinted wall which offers about 95% privacy as there is a slight gap along the wall. We live in a corner unit that faces East and there is nothing behind us or beside us to the North so I often walk out form the shower and towel myself off. The good thing is the glass surrounding the terrace is heavily tinted so standing there nude is of no concern. Many times I have sat out there in the nude to read a book, just enjoy the day, get head, fuck the GF or just fall asleep. There is small patio set out there and we have made use of the table many times while fucking. A few weeks ago was one such time.

    During the quarantine period I have been home bored as shit along with the 50 year old MIL Dana but the GF has been working still (City employee) and working OT so she is tired when she gets home. Dana has seen me nude many times as she has caught us fucking on the terrace, me sitting out there after a shower or getting a drink at night in the kitchen. A week ago I showered and went out on to the terrace to dry off to find my MIL sitting there. Well the chair is right beside the door so as I exited my junk was basically 2' from her face so she had a good look. There has always been flirting between us so I elected just to carry on as I normally would by drying off and sat opposite her while remaining naked. She spoke up and told me that it was not a good idea that I remain naked as she has not been with or seen a man naked since her husband passed away 5 years ago. I laughed it off and made some smart ass remark back to her.

    About 10 minutes later she put her book down and asked if I wanted a drink as she went inside. Moments later she returned with a drink and wearing a very see through teddy causing my cock to pulsate with every heart beat and become engorged. She halfheartedly apologized asking if she caused my problem and declared that she did in fact cause this issue. She then mentioned that she would be willing to alleviate the problem if I would be sworn to secrecy. It took me all of 1 second to confirm that I indeed could. Placing her drink down on the terrace floor she made her way over to me before placing a towel at the foot of the chair. She went to her knees and began first by sucking my balls(I manscape which she appreciated) and gradually worked my shaft before engulfing it. She is every bit as skilled at giving head as her daughter and maybe more so. I was fingering her during this time in preparation for me fucking her. We took the party to the the table and she lay back holding her lags up in anticipation for me inserting my cock but I instead dove in and lapped at her pussy. This immediately drove her nuts as she squeezed my head so tightly as I lapped away. I actually chuckled and it was then she told me that her husband would never go down on her but expected her to do so for him when asked.

    I made her cum twice before standing up to insert my cock and began to slowly pick up the pace before my balls were slapping off her ass. It was then that I noticed Janice peering through the gap by the wall but this did not deter me as I continued to pound away the MIL's pussy. Dana stopped me and offered up something her daughter had never been willing to do which was anal. Janice was still there watching as I lubed up my cock and stuck a finger in Dana'a ass in preparation. With a bit of play I managed to get it in and soon enough I was working her ass just as quickly as her pussy. With Janice still watching I pulled out of the MIL's ass as she took to the floor and opened her mouth as I blew my load in to it. Dana milked every bit of cum from me as I sat back in the chair when she then mounted me once again until I went limp. I glanced over as we got up to shower and Janice was no longer there watching us.

    While in the shower I told Dana that Janice had been watching us the entire time which concerned her greatly as who knows what would be said if anything to her daughter. I told her I had a plan for Janice but it may take her help in getting her over here one day for it to happen. As I thought of what I might do I was sucked back to attention and proceeded to tit fuck Dana in the shower before finishing off in her mouth.

    the quarantine has been long but if this plays out the way it has so far I will be a happy man.

    #45790 — Comments (0) — May 22, 2020 at 9:58 AM — That's Juicy! (11) Remove It.

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