My Life

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By (Edited with Ginger)


Hello, my name is Allison, I’m a twenty-nine year old woman, married to my college sweetheart Jason, who is thirty-one and we live in Florida with our children. I’m a structural engineer employed at a local company who manufactures yachts and Jason works at home in his own company of financial advising. Needless to say he has the stay at home mom job. We met in college and I have been pretty reserved my entire life.

After college and getting married we decided to have kids and I immediately got pregnant with twins. We always wanted two we stopped there. Since then I have also regretted being shy and afraid to make decisions with my life other than getting married. A friend of mine introduced me to the idea of turning my husband into a cuckold to satisfy my needs because Jason is quite under-endowed and part of my frustration with life was his poor sexual ability. While I thought that was a horrible idea at the time, I contemplated it for several months. To me that was cheating and I wanted no part of it. I knew I needed more information. I then joined a couple of forums and read more about it over the months to include ordering a book which detailed a step by step process over six months. I decided if I wanted to explore my sexual fantasies, but still stay in love with my husband and married to him now was the time.

I started implementing the books process step by step and at the end of the six months he and I sat down to talk about our future. I explained to him his small penis isn’t enough for me and what I wanted going forward. I gave him two weeks to think about what he wanted. After the time had passed and very stressful two weeks of us giving each other the evil eye, he said he wanted what I wanted and wanted to make me happy. I was overjoyed and nervous at the same time. I explained it would take time for him to get over the feeling of me cheating on him, but in time it would pass and we will have a happy life and we would progress through this slowly. I explained my end goal would be to have a full relationship with another man or friends to include being on birth control and not using a condom. I would be sub to my boyfriend and allow to do as he wished while Jason would be sub to me and I would do with him as I wished. That night we had sex to mark the last time for a while.

As we both had decent jobs I scheduled plastic surgery to enhance my breasts. They stopped growing in high school and I was a C cup. I had the plastic surgeon pump them up to a small D. I attribute my larger breasts to significantly enhancing my self-confidence, and catapulting me into a modern, confident, demanding and sexual woman. At my friend’s advice I also had the surgeon inject a small drop of silicon under each nipple to make it seem like I’m excited and my nipples are hard all the time. After everything healed, I hit the gym hard and have turned into a workout freak. I also bought a new wardrobe and wear the tightest thing to the gym I’m allowed to, which means my nipples are always poking through my sports bra and the attention never stops.

I still had two steps left until I turned into a cuckolding wife, first, pegging Jason; and second, having sex with another man. Jason wasn’t too fond of trying this, but has since come around and I peg him regularly prior to going on dates. The rubber penis I insert in his rectum rubs against his prostate and gives him and orgasm of greater intensity than masturbation or regular sex. It also allows him to have multiple orgasm cumming several times. To me this sounds like a woman’s orgasm. Since I cum internally I think he can do the same. I also encourage him to moan loudly like he really wants to like a woman. Nowadays, Jason is my little Peggy and he is very comfortable with my strap on inside him. Sometime he gets hard sometimes he doesn’t.

Our favourite positions are missionary with me on top between his legs and his riding me while I sit down. His favourite finish position is him lying on his side next to me being a little spoon and I push my “dick” inside him while he pants and moans like a little high school girl having sex for the first time. Needless to say we haven’t had sex in several years and I don’t plan on going back. His penis just doesn’t satisfy me, it’s so small and useless. A new development is “sounding” where I slide a metal rod with a bead at the end down his urethra and it provides a quick pleasurable sensation. We usually sit down next to each other with his arm around me and I lube the end of the sounding rod and slowly work it back and forth until it goes all the way down past his balls. This technique makes him cum quickly as well. I would love to get him to the point where he eats his own cum, but we have a little ways to go on that one.

Getting back to my story I still haven’t had sex with another man, which is where my friend who mentioned this from the beginning comes in. She has a very nice looking hubby which is why we all became friends quickly, I think he liked me. While he isn’t a cuckold, they both swing regularly and asked me to come over so they could help me with the transition into the cuckold lifestyle. I told Jason I had a date and he immediately started sweating bullets. I calmed him down and told him I was having dinner with our neighbours and tonight I was going to have sex with her husband so when I got home things might be a bit different but I would still love him. I walked over to their house nervous as hell. We all ate dinner, then talked a bit on the sofa. Julia came over to me and gave me a hug and kiss and said to just let it happen and enjoy.

We both took turns sucking on Trevor then he pulled away and turned Julia over and slid his erection all the way up inside her. After a couple of minutes of rubbing my hands over both he firmly told me to lay on my back. I laid down and he pulled his hard penis out of Julia and put it inside me. His cock was much bigger than my hobbies, which I knew he would be as Jason’s dick is like a little boy. However, I was unprepared for the following emotions to hit me like a train. I was relaxed and relieved to finally have done this and was not ashamed what so ever. I came within thirty seconds. Trevor turned me over on my hands and knees and immediately pushed it back in and made me cum several more times. After that, he finished with his wife and then we all talked while hands wandered all over the place lol. He didn’t wear the condom like he said he would, I guess he forgot, but I didn’t care as I was shaking. We planned out a schedule to continue for the next several months to build my confidence prior to releasing me into the “wild” to find a boyfriend. It pretty much worked like this. We and other couples would be invited over for a barbecue or to swim in their pool.

Afterward, when all the couples went home Julia would sit downstairs with Jason and talk to him while Trevor had his way with me upstairs. After all was over we would walk home together. Once we were comfortable with that, instead of talking to him Julia started to peg Jason while I got fucked by her husband. Later she pegged and sounded him regularly. Jason and I were known as the sub couple as I was also on my knees for Trevor and Jason was on his knees for Julia. After Jason and I got home, as the book said, I made him lick me to one more orgasm. Over the course of the next couple of months Trevor started to cum in me and we had sex as if we were married. Trevor was called to work unexpectedly, as he was an EMS tech, one night after he and I just finished having sex with him cumming in me. Since it was the three of us, Julia finished with Jason and led him over to me where she told him to get on his knees and lick me. Once he realized he was licking cum that was leaking out of me Julia pushed his head in and told him to get used to it which he did and he licked. He may not have liked it, but he continues to lick me clean after I have come home from a date to this day. That’s also where he first licked my ass and does so frequently to this day when I tell him.

Since I have started this new lifestyle I have been incorporated into Julia and Trevor’s family and have attended a couple of their parties they host for their swinging club. I’m proud to say I have opened my mind to all sorts of wonderful things and participated in threesome’s, foursome’s and more. Since I am not brining a male to swing with I’m only considered a visitor, but one they always enjoy having as I have met many friends through this group. I have been doubled penetrated by two guys, have started to grow a liking to girl’s although I have always kissed them and have never been afraid to do so. Since this is a new side of my life I have told my hubby about something’s but not others as I consider them to be private. I have developed an extremely flirtatious side as I flirt with all Jason’s friends and they know they can give me a hug with a nice pat on my ass whenever they want.

I will talk about any subject in front of anybody and talking about my body or sexual desires in front of my hubby does not bother me, it’s his feelings to get over lol. I have had four boyfriends in the last couple years, excluding Trevor and with my current we don’t use condoms and he cums in my mouth, pussy or ass. I am on a strong dose of birth control so I’m not worried about pregnancy. From the beginning Jason and I have set aside one and a half days for me to spend some time with my bf and maintain a physical relationship or to explore. My new best friend is my ass as I love the pleasure it gives me and continue to advocate to my boyfriends to take my ass regularly and fill it at the end. I have a small runway above my lips and because I have dark hair it is very evident when I wear see through panties under my skirt if I wear them. I prefer not to as it feels better.

At times I will shave it off and then look at myself in the mirror while I wiggle my butt back and forth and feel like a little high school girl again, definitely look like it being bare. My (fifty year old) acts more like a dad than a boss at work and is aware of my new-found sexual freedom and supports it as I encourage him to give me a hug whenever he wants to and of course take his time feeling my bottom. While I could file a sexual harassment suit against the company, but as I have received a couple raises and promotions I don’t mind the wink, ass pat or when he just leaves his hand there for a couple of minutes while we look at blue prints. Please don’t get me wrong, I’m not the type to spread my legs on the first date and I don’t do one night stands as I am a mom and can’t afford to be sick. I prefer to know the person before I start getting physical.

Jason and I bought a new house as we need more room because the one we live in is more of a new couple’s starter home. I haven’t figure out how I’m going to pay for the move yet. I have asked my boss as a favour to allow me to use company money but he had some reservations. I’m wondering if I propose that our weekly meeting between him and me in his office to review my projects become more of a topless meeting or panties only meeting to see if I can sway his decision to let me have the money. I don’t have much else to say except Jason’s feelings of anxiousness and embarrassment have dwindled to almost zero. He has no problem talking about me having nasty sex with some guy to watching anybody kiss me and sliding their hand down my shirt and squeezing my breasts. We still very much love each other and will continue to stay married.

We both still consider ourselves sub as I am usually sub to any guy I meet or interact with to include women if they show a strong side except Jason. He is sub to me and the world and he knows and accepts it.

If you would like to contact me or Jason about our lifestyle to make comments or ask questions we will be happy to respond to all emails and all cute pet names. I will respond to both men and women as Jason will and if there are any lady’s out there who read this who would like to call him and embarrass him on the phone please don’t hesitate to ask for our phone number.

Hope you enjoyed this and please pass it along.

Love Allison

One comment

  • S J Meyrr

    Stop birth control and make him watch you get bred.


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