An adventure I had after college
After I graduated from college I moved to the SF Bay Area and got a job at a high tech company. A lot of my friends were there too and we had a blast. After a few years I moved into an apartment in Menlo Park and it was in a complex with a pool and a lot of older people people living in it. Anyway, I had a girlfriend and life was great.
After I had been there a few months I met a couple that lived on the same floor a few doors down from me. I was 29 at the time and I think the husband was 60 something and the wife was in her late 50s. They were super nice and I frequently helped them bring stuff in, and ran into them at the grocery store, hallway etc. One day I ran into them in the elevator, we were chatting and they invited me to dinner. They knew I had a gf since they had seen her around too and invited her but she was out of town on business the day of the dinner. I accepted their offer since I was available and showed up on the day with a bottle of wine. Dinner was fine and we generally had a good time. I found out that the husband had retired, they had grown k**s living nearby and that they also owned a place in Palm Springs that they went to in the summer. All in all they were great people. I ended up going over for dinner a few more times and we also started occasionally (once a month or so) hanging out for some drinks, wine etc.
Let me describe them as well. The husband, lets call him Mark, was as I mentioned was in his 60s, 6'1" or so, balding and pretty chubby, probably weighed 260 or so. The wife, lets call her Maggie, was in her late 50s, 5'9" or so, blonde hair (natural I later found out) with a very nice round ass and some decent size boobs (C or D cups). She was not super fit but not bad for her age. She also was very nice looking and probably was quite a looker when she was younger.
One day I was at work and got a message (I had a pager...yes that old) asking if I wanted to come over for a glass of wine on Friday. My gf was doing something else and I had no plans so I said sure. That Friday after work I picked up a bottle of wine and knocked on their door. They had some apps out and we drank wine and hung out. After polishing off close to 3 bottles I excused myself and told them I had to go home. Maggie walked me to the door and as I was about to leave she turned to me and said she wanted to ask me something and that it was ok if I said no. I was a little puzzled (and buzzed) but I told her to ask. She told me that she wanted to come over to my apartment. I was buzzed and clueless and said sure, her and Mark could come over anytime. She then emphasized that no, SHE wanted to come over tonight. I looked at Mark who was sitting on the couch looking at us and asked her "without Mark?". I was really clueless. She said, yes. I was still unsure what was going on so I asked her if it was ok with Mark and he waved and gave me a thumbs up from the couch. Since I was buzzed, still a little unsure of what was going on I said sure and told her come along. She told me that I should go and that she would come over in a bit. She then gave me a kiss on the cheek, I waved to Mark and went to my apartment. When I got in I was still unsure of what was happening but decided to give the place a quick pickup. After I'm not sure how long there was a knock on the door. I opened the door and there was Maggie in a different dress and with a bag. I let her in and after I closed the door she turned around and kissed me on the lips. That was a surprise and after the kiss ended she told me what was going on. Apparently Mark had prostate cancer and after the surgery he was no longer able to get an erection. They had discussed getting him some surgery but decided not to. She told me that they still played around and that he could cum but just couldn't get hard. After they met me they discussed potentially asking me to fill in (pun intended) where he couldn't. She asked if I would be interested and I obviously said yes and that I was honored. She also mentioned that they had been married for 40 odd years and that she had never had sex with any other man in her whole life!!! Wow! She asked me to sit on the couch and then went into the bathroom with her bag. A few minutes later she came out wearing this little teddy with some sexy underwear underneath. She looked really hot and she sat next to me grabbed my hand and put it on her leg. We started making out and she was really into it. I started moving my hands around to her tits, pussy, ass and in no time I had her bra and her panties off. She had a nice bush of blonde hair and was already dripping wet. I was still dressed at this point so I stood up and started taking my clothes off. Once I got my underwear off she said "Wow! I did not know it was going to be that big!" She also had never seen a shaved and uncut cock since her husband is cut. I stroked it for her and pulled my foreskin back to show her the head. I walked towards her stroking my cock and put it in front of her face. She took the hint and started sucking me. For a lady who had only played with one cock her whole life she did a good job sucking me hard. Once stiff I made her stop, pulled her off the couch and took her to my room. I pulled her babydoll dress off and we got on the bed. Her tits were nice with big nipples and I started sucking on them as I fingered her pussy which as I mentioned was soaking wet. I spread her legs and started fucking her. She had her eyes closed and was shaking her head trying not to moan. A few times she grimaced a little and asked me to not go so deep (I bottomed out). I fucked her for a good amount of time in missionary position then I flipped her over and entered from behind. Her ass was very hot to watch as I pounded her pussy from behind. I also spread her cheeks to check out her butthole and to my surprise it was very nice and tight. I slipped a finger up her ass as I fucked her and heard no complaints. We fucked for quite a while in a variety of positions and I kept fingering her butt. I was lasting quite a while which was actually something I normally don't do and she eventually asked for a break. I got up and got some waters for us and as I came back she told me that it was the best sex she had ever had. We chatted for a bit and soon I was ready to start fucking again. I flipped her over and entered her from behind again since I am a butt guy. As I fucked her and fingered her anus I decided to see if she would let me fuck her ass. I pulled out and started rubbing my head on her anus. She turned around and told me that she had never done that. I told her that we could stop at anytime if it felt bad but that I loved it. She told me to go slow so I put it in her pussy got it nice and slick and started pushing it in her ass.
As soon as my head slipped in she asked me to stop. I left the head in and let her get used to it. Then I pushed a little more and stopped, pushed some more and stopped. This went slowly but soon I had 4 inches or so up her ass. I then started pumping and man, her ass was tight and it gripped my cock like a vise. In no time at all I told her that I was going to cum. She was surprised and asked "In my ass?" That was it and I started cumming like a fountain. It was one of the most intense orgasms I have had. I must have shot like a quart of cum up her butt. I was spent but I just left my cock up her ass while we rested. Eventually I pulled out and she rushed to the bathroom to clean out my cum enema. I grabbed and towel and to my surprise my cock was totally clean. She came out wrapped in a towel and we chatted some more. She thanked me, I thanked her and she got dressed and went home.
This was the start of about an year and a half of me fucking her every other month or so. On a few times her husband wanted to watch which was fine with me. He would mainly sit and watch and play with his limp cock. He actually only took his pants off once and would just pull his limp cock through his zipper. A few times he actually came which was wild since his cock never got hard and except for the one time he took his pants off I couldn't even see his cock. I also got her some dildos, took her to a drive-in movie and made her give me head and fucked her ass almost every time we hooked up. She never managed more than half my cock up her butt but it always made me cum.
I eventually moved out to a different place and saw them a few more times and eventually they moved to Palm Springs permanently. I love older women.
After I had been there a few months I met a couple that lived on the same floor a few doors down from me. I was 29 at the time and I think the husband was 60 something and the wife was in her late 50s. They were super nice and I frequently helped them bring stuff in, and ran into them at the grocery store, hallway etc. One day I ran into them in the elevator, we were chatting and they invited me to dinner. They knew I had a gf since they had seen her around too and invited her but she was out of town on business the day of the dinner. I accepted their offer since I was available and showed up on the day with a bottle of wine. Dinner was fine and we generally had a good time. I found out that the husband had retired, they had grown k**s living nearby and that they also owned a place in Palm Springs that they went to in the summer. All in all they were great people. I ended up going over for dinner a few more times and we also started occasionally (once a month or so) hanging out for some drinks, wine etc.
Let me describe them as well. The husband, lets call him Mark, was as I mentioned was in his 60s, 6'1" or so, balding and pretty chubby, probably weighed 260 or so. The wife, lets call her Maggie, was in her late 50s, 5'9" or so, blonde hair (natural I later found out) with a very nice round ass and some decent size boobs (C or D cups). She was not super fit but not bad for her age. She also was very nice looking and probably was quite a looker when she was younger.
One day I was at work and got a message (I had a pager...yes that old) asking if I wanted to come over for a glass of wine on Friday. My gf was doing something else and I had no plans so I said sure. That Friday after work I picked up a bottle of wine and knocked on their door. They had some apps out and we drank wine and hung out. After polishing off close to 3 bottles I excused myself and told them I had to go home. Maggie walked me to the door and as I was about to leave she turned to me and said she wanted to ask me something and that it was ok if I said no. I was a little puzzled (and buzzed) but I told her to ask. She told me that she wanted to come over to my apartment. I was buzzed and clueless and said sure, her and Mark could come over anytime. She then emphasized that no, SHE wanted to come over tonight. I looked at Mark who was sitting on the couch looking at us and asked her "without Mark?". I was really clueless. She said, yes. I was still unsure what was going on so I asked her if it was ok with Mark and he waved and gave me a thumbs up from the couch. Since I was buzzed, still a little unsure of what was going on I said sure and told her come along. She told me that I should go and that she would come over in a bit. She then gave me a kiss on the cheek, I waved to Mark and went to my apartment. When I got in I was still unsure of what was happening but decided to give the place a quick pickup. After I'm not sure how long there was a knock on the door. I opened the door and there was Maggie in a different dress and with a bag. I let her in and after I closed the door she turned around and kissed me on the lips. That was a surprise and after the kiss ended she told me what was going on. Apparently Mark had prostate cancer and after the surgery he was no longer able to get an erection. They had discussed getting him some surgery but decided not to. She told me that they still played around and that he could cum but just couldn't get hard. After they met me they discussed potentially asking me to fill in (pun intended) where he couldn't. She asked if I would be interested and I obviously said yes and that I was honored. She also mentioned that they had been married for 40 odd years and that she had never had sex with any other man in her whole life!!! Wow! She asked me to sit on the couch and then went into the bathroom with her bag. A few minutes later she came out wearing this little teddy with some sexy underwear underneath. She looked really hot and she sat next to me grabbed my hand and put it on her leg. We started making out and she was really into it. I started moving my hands around to her tits, pussy, ass and in no time I had her bra and her panties off. She had a nice bush of blonde hair and was already dripping wet. I was still dressed at this point so I stood up and started taking my clothes off. Once I got my underwear off she said "Wow! I did not know it was going to be that big!" She also had never seen a shaved and uncut cock since her husband is cut. I stroked it for her and pulled my foreskin back to show her the head. I walked towards her stroking my cock and put it in front of her face. She took the hint and started sucking me. For a lady who had only played with one cock her whole life she did a good job sucking me hard. Once stiff I made her stop, pulled her off the couch and took her to my room. I pulled her babydoll dress off and we got on the bed. Her tits were nice with big nipples and I started sucking on them as I fingered her pussy which as I mentioned was soaking wet. I spread her legs and started fucking her. She had her eyes closed and was shaking her head trying not to moan. A few times she grimaced a little and asked me to not go so deep (I bottomed out). I fucked her for a good amount of time in missionary position then I flipped her over and entered from behind. Her ass was very hot to watch as I pounded her pussy from behind. I also spread her cheeks to check out her butthole and to my surprise it was very nice and tight. I slipped a finger up her ass as I fucked her and heard no complaints. We fucked for quite a while in a variety of positions and I kept fingering her butt. I was lasting quite a while which was actually something I normally don't do and she eventually asked for a break. I got up and got some waters for us and as I came back she told me that it was the best sex she had ever had. We chatted for a bit and soon I was ready to start fucking again. I flipped her over and entered her from behind again since I am a butt guy. As I fucked her and fingered her anus I decided to see if she would let me fuck her ass. I pulled out and started rubbing my head on her anus. She turned around and told me that she had never done that. I told her that we could stop at anytime if it felt bad but that I loved it. She told me to go slow so I put it in her pussy got it nice and slick and started pushing it in her ass.
As soon as my head slipped in she asked me to stop. I left the head in and let her get used to it. Then I pushed a little more and stopped, pushed some more and stopped. This went slowly but soon I had 4 inches or so up her ass. I then started pumping and man, her ass was tight and it gripped my cock like a vise. In no time at all I told her that I was going to cum. She was surprised and asked "In my ass?" That was it and I started cumming like a fountain. It was one of the most intense orgasms I have had. I must have shot like a quart of cum up her butt. I was spent but I just left my cock up her ass while we rested. Eventually I pulled out and she rushed to the bathroom to clean out my cum enema. I grabbed and towel and to my surprise my cock was totally clean. She came out wrapped in a towel and we chatted some more. She thanked me, I thanked her and she got dressed and went home.
This was the start of about an year and a half of me fucking her every other month or so. On a few times her husband wanted to watch which was fine with me. He would mainly sit and watch and play with his limp cock. He actually only took his pants off once and would just pull his limp cock through his zipper. A few times he actually came which was wild since his cock never got hard and except for the one time he took his pants off I couldn't even see his cock. I also got her some dildos, took her to a drive-in movie and made her give me head and fucked her ass almost every time we hooked up. She never managed more than half my cock up her butt but it always made me cum.
I eventually moved out to a different place and saw them a few more times and eventually they moved to Palm Springs permanently. I love older women.
2年前
