My future wife and I had started dating in college. We were living together from day 1. I was sweet and charming and I thought she was out of my league. But she seemed to love me despite my average looks. She was a virgin and I was not. I had had sex with a couple girls in high school, each one time only. I know it was my small dick at not even 5” that led to no repeat performances. My girlfriend wanted to be in a relationship longer than the ones she had been in in high school with only 3 months being the time to beat. We got there and she said she was ready. Growing up “catholic” she was fairly innocent and did not masturbate. At least until we had sex. At first she wanted to keep trying, but soon we both realized that she was not getting anything out of sex with me, even though I was having the time of my life. The more we tried different things to make it work the more she started masturbating and collecting toys. We got to the point she could orgasm during sex when she would stick all four fingers in her pussy while I was fucking her and she would use her thumb to stimulate herself from the outside. I had always liked most kinds of porn but the idea of having a cuckold relationship always turned me on faster than anything else. I like a lot of things about it. Showing off my hot girlfriend to other guys and letting them try her out like giving a buddy a ride in a new convertible.
Even before we had sex there was playful banter about her other boyfriend. I am on the small side of average. And once we started having sex I could only ever make her cum with my hands or hands and mouth but not my dick. She wasn’t sexual at all growing up, and now was making up for lost time. When I first took her virginity she had been 20 for a couple months and had never masturbated or seen a dick in person. I was 18 and had only had sex a few times myself. Needless to say it was only mind blowing perfect sex for me. But she loved it when I could make her cum. I quickly found out that was primarily with my fingers. She loved my fingers and sometimes my mouth (she had to be in the right mood because she didn’t like giving oral back very often and it would make her feel guilty). The only time my dick made her cum was when she was drunk, which wasn’t often enough I guess. Almost from the beginning our talk in bed was dirty. That would have been her best quality in bed had it not been for her D cup boobs and overall knockout body. Right before summer she asked one time after sex if I was kidding about the talk of her with other guys. After I had shared my fantasy about being a cuckold, she wasn’t sure what to think at first but she enjoyed bashing my dick in bed. I could be fucking away, not ready to finish at all and she knew what would push me to the edge. She would be done with my humping and would say a string of things insulting my dick and my fucking her and that would be the end for me.
Summer came and she was going to do the same job she had done last summer. She had an internship with the forest service and during the summer would go on 1-4 week assignments to help fight forest fires. She worked out of base camp and had worked with this girl Stacy on a fire last year. Stacy didn’t have a boyfriend but enjoyed the company and wallets of the firefighters that came to base camp in the evening for the night. Stacy would either put her tent up away from the rest of everyone else or back it up to a wooded area that she could retreat back into and let the boys come to her.
It just happened that the first fire my gf went on that year Stacy was there too. My gf was curious and asked Stacy more about her nights. It took Stacy a couple nights to convince my gf to move her tent over next to Stacy’s. The first two nights Stacy had her in her tent with her and gave her the smaller dicks, my gf loved it. She only took five guys the first night as she began to work up her sexual stamina, but came for every one of them. After retiring to her tent she fell asleep to Stacy continuing to take guys just a few yards away. Stacy gave my gf bigger and bigger cocks to deal with every night and after the first three days made her do the week of her 2 week assignment by herself. She had a couple more assignments that summer and I could not get enough of the dirty texts I got while she was on the fires and the stories when she would come back from one.
During her junior year things were quiet again as I guess neither of us were ready to bring other guys into our life and we survived off of her stories from that summer. The next summer came and she couldn’t wait to go out on her first job. It took no advertising for a line to be at her tent when she got off on the first night.
One story I got was: Once they took me outside under the stars behind my tent so there was more access to put dicks in my hands and between my boobs. They ended up finding a small table and tying my legs a painful distance apart along the long way of the table. As far into the split position as I go. One would fuck my pussy and another had my head tilted backward of the other side of the table sticking his dick down my throat. My hands were tied toward the other two corners my feet were not tied to and were almost always stroking two more dicks while a fifth guy got on top of me and fucked his dick between my tits. I don’t know how many guys were there that night but my neck and legs were sore for a week. At first when they were done the few left standing around who had just finished left me tied to table dripping from head to toe in sticky white cum. A lot of it had dried but with the heavy dew that morning it all got wet again. Eventually they untied me from the table but left the ropes on my arms and two of them pretty much carried me behind a water truck. They tied my arms to a thick low hanging branch just above my head and hosed me down. They were cruel with the water pressure and while they were my most dirty parts sprayed my pussy and tits more than they needed. I pleaded with them to turn it down but they just said why? You are going to let us fuck you again tonight. And I knew they were right. When they were done they released my hands and walked away. I collapsed into the mud whole that had been created by my cold shower because I could not stand yet. I lay there in the freezing mud knowing if I didn’t work up the strength to stand soon I would be late for my shift. I got myself to my tent and wrapped myself in a towel before heading to the shower to get a few moments of warm water to clean the mud off and try and drain more cum out of my still full hole.
By the end of this second summer my girlfriend had become addicted to dicks. And lots of them. Her previous school year job as a nanny wasn’t going to work her senior year because of the limited selection of classes she had left. She got a job in the country bar in town and started driving all the guys at school who were 21 crazy with her cowgirl boots and daisy dukes. My school year job was at a fast food place a good 203- minutes away and by the time I had helped close up at night I knew she was already home at our apartment in our bed with a guy or two. Sometimes they would already be gone by the time I got home, and sometimes I got to watch them finish before I got sloppy seconds.
She graduated from college the next spring. Her parents had paid for all her college and she had worked hard every summer as I have told you and saved most of that money. Her and a friend decided to open up a small county bar in the town one over from where we went to school. It didn’t take people who had fucked her before long to find her in her running that bar. It wasn’t long after that that we bought a new mattress and bedframe for our bedroom and moved the old one into the back room at the bar. I don’t know if she was really getting fucked all day long, but that’s what she was telling me, and the bar was raking in some good money.
When our cuckold relationship started I had told her I would be ok with it on three conditions. One, she wasn’t picky. She had to fuck and/or suck every hard dick she was presented with. If she made a guy hard, she should drain his balls. Two, that because she was a sluty dick loving whore, she deserved to be punished by me. The number was really never set but it was somewhere between cheating on me with 12-20 dicks that I got to fuck her. Sometimes this was every night for a week, and if it was slow in her pussy for some reason she would normally just tease me and tell me she needed to be a naughtier girl tomorrow if I wanted anything. And three, she had to tell me all about them.
After I graduated I was working hard too to bring in my share of the money in so we could buy our first house and further my new career. Our normal routine was I would get up in the morning and be at work by 7 or earlier. I was regularly working 12-13 hours a day and would text her when I about an hour warning to my being home. I think some of her regulars about this time would get my text and tell her to start wrapping up. She had some of them trained in how I liked her to come home. They would tip her hips way up, dump a couple loads in her, when the last guy that was going to fuck her pussy pulled out they would sink a vibrator that was about the size of my dick into her pussy and put a piece of duck tape over her sore pussy leaving as much cum as possible trapped inside. Then they would flip her over and had a few guys cum in her ass and sink a giant butt plug in her ass that wouldn’t let any cum run out. Then she would pull on her shorts or her mini skirt, without underwear and her shirt and drive the 5 minute drive home to wait for me to punish her. She normally knew if she was going to go back after I punished her when she was leaving and would tell the guys if she thought she would be back in an hour and a half or so. Normally on busy night she would always go back. So I would come home and find her naked on the bed rubbing her tits and her pussy through the tape, covered in dry cum from the day’s activities.
Sometimes I would just fuck her and sometimes I would tie her up. Tonight I tied her up. Her arms were to either side of the bed and I tied her ankles to the top of the headboard pulled her legs up and apart similar to how they finished fucking her pussy. I blindfolded her and then got out the nipple clamps. She didn’t like when I used these for some reason. She got her tits roughly squeezed and pulled on all day long and would tell me she loved it but she hated when I put these on. When I would take them off she loved for me to suck her poor wounded nipples though. So there she was blindfolded, tied up with her normal duck tape and butt plug while she tells me about this young stud, or that old fat guy, or this dirty black homeless man. This huge dick, that tiny dick that fucks better than me, taking two at once in her pussy or ass and every other dirty thing that happened that day. I have a small whip and I start whipping her tits and pussy. Not real hard, and this she loves. She starts talking so dirty and telling me to punish her. I will work up the corner of the duck tape so I can rip it at any time. That is not her favorite part, getting the tape ripped off, but she knows I love when she brings other guys cum for me and spills it all over our bed. I rip the tape off and then yank the butt plug out immediately after. Two rivers of cum start flowing and join to make a growing puddle on the bed. The vibrator slides right out of her stretched out pussy, too small for the walls of her pussy to hold it in. I start working in my hand until I am fisting her and she is still talking dirty to me about her day. I do that for a little and then decide its time to fuck her. I absolutely love the feeling of gaping pussy barley squeezing my dick at all. She hates it, at work she prefers normal dicks two at a time or in her mouth. But this is her punishment. She starts laying into me about my useless dick. How much me fucking her drives her to want more real men. While I love the feel of her stretched out pussy it is so big now I can actually very rarely go off without a smaller pussy. No matter how dirty she talks anymore I rarely do it. She will beg for me to release one of hands and I will eventually give in and she will immediately cram four fingers and her hand in up to her thumb giving us both a better experience.
Like I said when I am all done she often wants to go back to work. She will take a shower though and pretty up again, like she did this morning. I will put the butt plug back in her and she will go back to the bar. Once she let me go ahead of her, and only her friend who runs it with her knows who I am and I watched her entrance into the bar, looking like a slutty country girl with her ass and tits hanging out and she was mobbed by almost a dozen guys kissing and grabbing her ass and tits. I didn’t think they were going to make it into the back room but they did and more guys followed. She had let me come in there once and participate so I could see how much of a whore she really was. That was the greatest day of my life. So I would go to sleep in the pile of cum that came out of her pussy and sometimes I would wake up in the morning and she would have come back and was laying next to me covered in cum again. Sometimes she wasn’t and I knew she had had a long night that night.
I would be at work by the time she came home to do her daily workout, shower, and put on her slutty clothes and makeup for that day. The bar opened at 11:30 and she was back on that old bed by 12:30 most days. There were several guys that came in the middle of the day, including several homeless men, but this was really a warm up session. She normally stopped to clean up some in the bathroom off of this room which had a shower around 3:30-4 to work for an hour or two before starting in on the evening session that went until I interrupted. She knew by now if she had had enough that day and was going to come back after getting her punishment.
Her friend who opened the bar with her wasn’t servicing the customers the same way my wife was. She was normally dating one, but that guy seemed to change almost every month. Normally she caught them going in or out of the back room to fuck my wife. She had been friends with us all through college and found out about our relationship and thought it was hilarious. How much she loved dick and how much I loved her to get it. Her friend was a little on the plump side, but blonde, amazing tits, a full ass, and dressed with confidence. She was always looking cute and had her huge cleavage showing. She was 5’2” before her boots, but also wore 4” heals on a regular basis. I don’t know how big her tits were, but they were much bigger than my wife’s. They were big in that bbw way and I had always wanted to know how her tits and ass felt. This came up somehow one time and a few month later, right after a breakup with her latest boyfriend I came home to not my wife but her friend. She said that wife didn’t want to leave the real dicks that night and that she hoped she was an acceptable stand in to dump my load into. Let me tell you, those tits were amazing, and that ass felt so good as I fucked her from behind. I actually had dinner made for me that night and not brought home from the bar like my wife always did. This became a regular thing, two or three times in a week between boyfriends until some of my wife’s regulars figured out what was going on. They started trying to sabotage any potential relationships my wife’s business partner was getting into to keep her available for me. She actually found this humorous too and decided she had been having no luck with men her whole life and that she would take a break from dating. All of a sudden it was like having two wives. Almost every other night it was her friend I found when I came home. She seemed to like our new fwb/stand in wife relationship, and also got into getting tied up and talking dirty humiliating things to me in bed sometimes too. One time after three nights in a row I thought I might have a new wife with a decent pussy I could get off in. And it was nice waking up to someone every morning again. But night four, there was my beautiful wife, as gaping as ever. I left her tied to the bed that night so she couldn’t run away. She said that when her friend found another boyfriend she was going to have to find another stand in for her because she just hated having to come home to my little dick every night.
My life was full of cuckold stories for the next 14 years or so. This is where I speed up my story telling to get to where I am today and tie back to my other stories. Somewhere in there we got married and were trying to have a child unsuccessfully. I was 33 and she was 34 when we finally decided to adopt and through the foster system found a baby and one year old half-sisters. The week after paperwork was signed we found out my wife was pregnant. This is where my story changes. There were complications during birth and my wife did not make it. Both of her parents had been diagnosed with different forms of cancer within a month of each other during the pregnancy and a few months after the birth they both passed. I had had a good job since getting out of college. We owned our house and almost had it all paid for. The life insurance payout I got from my wife passing was substantial and then her parents were fairly rich and I got a third of that. During this time I was depressed and never wanted to work again just staying on the couch or in bed watching reality TV shows or porn. I had hired a nanny to take care of the three girls. Soon I realized I was going through my money to fast. I decided to move out of the US. I landed in a more tropical location, hired a local nanny and the misery continued. I gained weight and stopped taking care of myself. After almost two years of this I decided it was time to get back into the market and try to find someone to care about, and who would care about me. I was over 250 lbs. and my average looks in my teens and twenties had turned into below average now. Being in a tropical place there were a lot of tourists, and the single ones mostly laughed at my attempted advanced. I wasn’t attracted to the locals here, I had paid a couple prostitutes to have sex with me and a couple nannies. I was never really feeling it with them. I gave this up after a couple months and continued masturbating to porn, now doing it 3-4 times a day. I fired my latest nanny and decided to take an interest in my daughters. There was no school for them on the island, so they were homeschooled when I took the extra time to teach them. Mostly they played on the beach, around the house and watched TV. When they were 10 & 11 I found them secretly watching my porn and masturbating. This slowly evolved over the last 4 years into what it is now. There are lots of good stories of the last 4 years and of my wife before that that I can share with you. And more stories to come in the coming months and years I hope.
