Straight Male / 47
When I was 37 my wife and I were in a hard time. I was working full time making decent money but she was going to college and working at the same time. We had two kids too so it was tough but we figured out how to make it work. Then she ended up losing her job and we had to shift our lifestyle around. We had to figure out our money situation for the next year or till she could at least find a part time job.
Well Christmas was coming up, money was tight and we still were going to give our kids a good Christmas. They were little so they wouldn't have known a difference one way or another but still it ment something to us.
My wife got a part time job so we finally had that extra money flow but still I wasn't comfortable spending extra money. I was talking with some friends about Christmas coming up, we were both complaining about the overall pain in the ass it is. He jokingly said seek your ass for some money! We laughed but I seriously gave it a consideration over the new few weeks.
Finally ne night after sex I told my wife what I had on my mind. Told her we needed extra cash for Christmas and I could sell my anal virginity for money. There is a market for that. She said but you not gay and I said I'm. Not but I don't see it a problem taking a guy or two in my ass one night for extra cash. It's a simple way to make extra cash. Oddly enough she agreed and I was surprised. She was on board with the idea, I figured it'd just be a one time thing and I'd never notice or anyone would ever notice I got my ass fucked.
So the next night while my wife was in class the kids were at my parents house so I was at home alone. I shaved my ass smooth and shaved all my pubic hair off since I was all natural for many years. I took pics of me in doggy position on the bed with my asshole showing and pic of my now bald cock.
The process began as I made a Craigslist ad. I worded it to point out I only want an older wealthy guy to take my virginity. I posted the ad and within three days I had a guy email me. The offer was put up how much he'd pay me and where I would meet him at. He was staying in a hotel in a city an hour away for business stuff for a week. The deal was I'd come stay with him for the week, he'd have sex with me every night since he didn't get sexy from his wife anymore and he'd pay me at the end of the week. I had vacation time at work and told my wife the offer. She asked me if I was sure about this as once I get my ass fucked I'll remember it for the rest of my life. I said yes and I told the guy I'd meet him at his hotel
Two weeks later I went to meet with this older guy. He was 60 years old but looked younger. When I arrived we got all the hellos out of the way and he got straight to the point. He showed me test results showing he was std free and hiv negative. He also told me straight up we needed to walk down to the local store and get some lube before we have sex, no biggie so we went down to Walgreens and got the lube he preferred to use. But no condoms, I asked if he needed condoms. That's when he told me for the money he's giving me and he proved he was clean he was going to cum in me each time. I was okay with it as he was giving me money. Upon arriving back at his hotel he stripped off all his cloths except his underwear. He was wearing Hanes briefs and that's when I noticed this guy was packing some dick in them! He looked at me and told me to get down to my underwear. I stood there in my white briefs as he checked me out, he commented saying we'll pull those off and let's see that smooth body.
Finally he had me pull his briefs down. His hung cock flopped out. He had to be 8" and he was thick. He said he offered such good money to me because he was a hung guy and it was my first cock. He had me suck it. It was weird at first but I got used to it. I figured this wouldn't be bad. Finally the big moment, he had me lay on the bed on my back and hold my legs up. He lubed my hole up and his cock and he started to finger me at first. It felt okay ill say but after like 10 minutes he had his cock head against my hole and said this will probably hurt at first but you'll get used to it. He slowly pushed in and it did hurt. I sucked it up and just let him get inside me. I was no longer a virgin now. He fucked me for a good 10 minutes till he blew his load in my ass. I could feel it and when he pulled out I could tell my ass was gaping like my wife's after I fucked her ass.
So for the rest of the week he fucked me in the morning before taking his shower and at night before bed. By the third time it felt okay to me. I'd always just jerk off after sex myself as he cleaned himself off.
The whole week I was in nothing more than just my briefs usually, he was the same when he got back to the hotel. Well finally the last day was there and I waited for him to get back to the room to pay me as he said he would. I was dressed and ready to go as he walked in, he handed me the money in all 100s and thanked me. But he said your not finished yet, told me to drop my pants and underwear around my ankles and lean over the bed. He blew a big load in my ass one last time with his 8" cock and I pulled my briefs back up and my jeans. He thanked me as I got my stuff around and as he stood there with his pants around his ankles.
We walked out together and I drove him to the airport, he gave me a one last thanks and I definitely thanked him. So driving home with his cum deep in me and I could tell some was leaking out. I call my wife and told her I was almost home. I got home a d there was no kids so we have some very intense sex. Plus she was fingering my ass every chance she got saying it felt looser now! I said no worries it'll tighten back up. Funny thing is she told me, me taking it in the ass really turned her on. I was so surprised plus she was happy we had extra spending cash for Christmas too.
Well Christmas was coming up, money was tight and we still were going to give our kids a good Christmas. They were little so they wouldn't have known a difference one way or another but still it ment something to us.
My wife got a part time job so we finally had that extra money flow but still I wasn't comfortable spending extra money. I was talking with some friends about Christmas coming up, we were both complaining about the overall pain in the ass it is. He jokingly said seek your ass for some money! We laughed but I seriously gave it a consideration over the new few weeks.
Finally ne night after sex I told my wife what I had on my mind. Told her we needed extra cash for Christmas and I could sell my anal virginity for money. There is a market for that. She said but you not gay and I said I'm. Not but I don't see it a problem taking a guy or two in my ass one night for extra cash. It's a simple way to make extra cash. Oddly enough she agreed and I was surprised. She was on board with the idea, I figured it'd just be a one time thing and I'd never notice or anyone would ever notice I got my ass fucked.
So the next night while my wife was in class the kids were at my parents house so I was at home alone. I shaved my ass smooth and shaved all my pubic hair off since I was all natural for many years. I took pics of me in doggy position on the bed with my asshole showing and pic of my now bald cock.
The process began as I made a Craigslist ad. I worded it to point out I only want an older wealthy guy to take my virginity. I posted the ad and within three days I had a guy email me. The offer was put up how much he'd pay me and where I would meet him at. He was staying in a hotel in a city an hour away for business stuff for a week. The deal was I'd come stay with him for the week, he'd have sex with me every night since he didn't get sexy from his wife anymore and he'd pay me at the end of the week. I had vacation time at work and told my wife the offer. She asked me if I was sure about this as once I get my ass fucked I'll remember it for the rest of my life. I said yes and I told the guy I'd meet him at his hotel
Two weeks later I went to meet with this older guy. He was 60 years old but looked younger. When I arrived we got all the hellos out of the way and he got straight to the point. He showed me test results showing he was std free and hiv negative. He also told me straight up we needed to walk down to the local store and get some lube before we have sex, no biggie so we went down to Walgreens and got the lube he preferred to use. But no condoms, I asked if he needed condoms. That's when he told me for the money he's giving me and he proved he was clean he was going to cum in me each time. I was okay with it as he was giving me money. Upon arriving back at his hotel he stripped off all his cloths except his underwear. He was wearing Hanes briefs and that's when I noticed this guy was packing some dick in them! He looked at me and told me to get down to my underwear. I stood there in my white briefs as he checked me out, he commented saying we'll pull those off and let's see that smooth body.
Finally he had me pull his briefs down. His hung cock flopped out. He had to be 8" and he was thick. He said he offered such good money to me because he was a hung guy and it was my first cock. He had me suck it. It was weird at first but I got used to it. I figured this wouldn't be bad. Finally the big moment, he had me lay on the bed on my back and hold my legs up. He lubed my hole up and his cock and he started to finger me at first. It felt okay ill say but after like 10 minutes he had his cock head against my hole and said this will probably hurt at first but you'll get used to it. He slowly pushed in and it did hurt. I sucked it up and just let him get inside me. I was no longer a virgin now. He fucked me for a good 10 minutes till he blew his load in my ass. I could feel it and when he pulled out I could tell my ass was gaping like my wife's after I fucked her ass.
So for the rest of the week he fucked me in the morning before taking his shower and at night before bed. By the third time it felt okay to me. I'd always just jerk off after sex myself as he cleaned himself off.
The whole week I was in nothing more than just my briefs usually, he was the same when he got back to the hotel. Well finally the last day was there and I waited for him to get back to the room to pay me as he said he would. I was dressed and ready to go as he walked in, he handed me the money in all 100s and thanked me. But he said your not finished yet, told me to drop my pants and underwear around my ankles and lean over the bed. He blew a big load in my ass one last time with his 8" cock and I pulled my briefs back up and my jeans. He thanked me as I got my stuff around and as he stood there with his pants around his ankles.
We walked out together and I drove him to the airport, he gave me a one last thanks and I definitely thanked him. So driving home with his cum deep in me and I could tell some was leaking out. I call my wife and told her I was almost home. I got home a d there was no kids so we have some very intense sex. Plus she was fingering my ass every chance she got saying it felt looser now! I said no worries it'll tighten back up. Funny thing is she told me, me taking it in the ass really turned her on. I was so surprised plus she was happy we had extra spending cash for Christmas too.
- That's Juicy! 48
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