Cuckold Beginnings

I have spent hours upon hours writing the cuckolding experiences my wife and I have had over the years. Various reddit accounts, a very successful Tumblr back when it was great, and here I am on literotica. Writing about it is still the best outlet I have. I've been told I go into a lot of detail... hopefully that's in a good way. one thing about being a cuckold is you usually don't just hop into the lifestyle. Hopefully the slow burn of this becoming a reality will give you the insight into what it is really like.

From the top... My wife and I are in our early 30s now. We've been together for 11 years. We met in college in what was my junior year and her sophomore. We knew each other for a good six months before we started dating.

My wife is Ashley and she is 5'5" and about 115 lbs. She has brown hair and is a complete bombshell. She turns heads everywhere she goes and hasn't changed a bit since we were in college.

My name is James and I'm pretty tall, about 6'3", and in pretty good shape. When I met Ashley it was through mutual friends and I immediately wanted to marry her. She was gorgeous, so easy to hang with, and seemed interested in me.

It was one of those things for about six months where it just didn't line up. She'd start seeing someone or I'd have someone interested in me. Finally, we were both single. She was over at my apartment along with most of our friend group.

I had injured my perineum (taint) in a mountain biking accident and was feeling pretty rough. We'd been friends for a bit at this point but it was always flirty. She knew I was somewhat hurt and asked me what happened. One of my roommates was walking by and said, "He crushed his balls." She looked at him then back at me with wide eyes. I said, "Yeah no. They're good."

I told her what happened and she said, "Ouch... Did you get your balls in there (meaning between my taint and the bike seat) too?" I told her I don't even remember my balls hurting because everything else was hurting. She laughed.

All I could think of was how she and I were talking about my balls. I remember thinking I was either super friendzoned or she was interested. We had some alcohol in our system and she asked what was actually hurting. I said it was mostly nerves running down there. She said, "You broke your dick?" I chuckled a little and she slapped me on the shoulder and held out her drink to "cheers" me. She said, "May it rest in peace."

I laughed and said, "I'm not toasting to that!" I held out my drink and said, "To a long and happy life... For my dick." She started laughing, we clinked drinks, and changed the subject. We talked for another couple of hours and periodically welcomed others into the convo then they'd leave.

When I got up to go to the bathroom my roommate said, "Bro if you don't ask her out, I will." I knew he was kidding because he knew how much I liked her but it was his way of saying, "Shoot your shit, idiot." He was right. My heart was in my throat when I went back over to her. One of her friends was chatting with her now and I was annoyed like I'd missed the window.

I was determined now. Maybe it was the liquid courage. Eventually, people started leaving. I called out to her when she was walking with her friend to the door and asked motioned for her to come closer (to separate her from the group in case she said no).

I finally asked her if she would want to go out the next night to grab dinner. She made a little grimacing face and said, "Ooph. You waited until you crushed your balls to ask me out?" I am usually quick on my feet but searched quickly for the right words. I blurted out, "At least with a broken dick and busted balls you know my intentions will be pure." Right when I said it I was mortified but she laughed really hard, blushed, and said she'd love to go out.

I didn't realize it while we were talking because I couldn't believe it was happening, but when I was alone later I realized how hard it got me with her talking like that. I jerked off through the pain.

The next night I picked her up and I'll never forget her in that short white skirt and lacy black top. She had white sneakers on, which made it feel a little more casual. We had the best night of my life up to that point. We laughed so hard over dinner, we ended up going bowling, and then we just hung out in the parking lot outside of my car outside of her apartment. Her roommates were in side so we were enjoying the "solitude" of being outside.

Out of nowhere, she kissed me. I couldn't believe it. I kissed her back and we started making out. I kept my hands in respectable spots and she had her hands in my hair. I felt my dick get hard and honestly it was a little painful. She was right up against me and whispered, "I guess it is working." I chuckled nervously.

I was inexperienced at this point. Embarrassingly so. I'd had sex with one girl and it was only a few times. I'd messed around with other girls but nothing crazy. Ashley has been in quite a few relationships and I'd seen her "date" other guys for short periods of time. My mind was thinking we'd say goodnight and I would go home. We'd do the traditional three days thing or something. I was terrified to mess it up.

She had me pinned against the car and put her head in my chest. I was 100% in heaven. I couldn't believe it. She then said, "It feels like we're on our 50th date to me." I said it did feel very normal. She then looked back at her apartment. "I don't want to go in there... Can we go to your place?" We knew her friends and mine (our friend group) were so excited we were on a date. I guess she knew her roommates would be annoying if we went in there. She suggested we go to my place.

I was shocked. I knew it meant she wanted to come inside and do something. The five minutes drive to my apartment felt like it took an hour. She had her hand on my thigh. We didn't talk much. She seemed super turned on. I was so hard. She apparently saw it through my jeans because all of a sudden she slid her hand to not just cover my thigh but put her hand on my dick and squeezed it.

My mouth was hanging open and I looked at her. She was staring at it and biting her lip. She said, "Do you mind that?" I said, "Absolutely not." She laughed because it was a weird way to say it. We finally got to my apartment and went inside very quickly.

One of my roommates was there but didn't bother us coming in and we went straight to my room. We kicked off our shoes and got in the bed. And kept making out. I kept thinking two things: "Don't fuck this up by going too fast" and "I can't believe she's initiating this."

I finally got the courage to put hand on her ass. It was on top of her skirt and she reached back and pulled the skirt out from under my hand. I pulled my hand off being way too respectful. She said, "No put your hand back, just getting my skirt out of the way."

Finally she pulled back and looked at me. She said, "I guess we shouldn't have sex yet?" I could tell she wanted it but we were young and trying to behave. I said, "Ugh. I guess not." She then said we could still "have some fun."

She started unzipping my jeans and I helped by taking off my belt. I felt pain pinging in my dick from the nerves still. That damn injury took weeks to fully heal. She put her hand in my jeans and was getting the lay of the land. She rolled my balls around some under my boxers and ran her fingers up and down my shaft.

"How are you feeling down here?" I told her there was some pain but it didn't matter. She said, "Aww poor guy..." She pulled her hand out of my jeans and we kept making out. I started kissing down her belly. I wasn't planning on going any lower but I felt her hand on the top of my head slowly and relatively forcefully urging me to keep going.

I'd never eaten a woman out before. I had fingered girls and had sex with the one... But it made me pretty nervous. I got down there relatively close to her pussy and she spread her legs wide. She had a black thong on, which I had noticed through her white skirt earlier. I know she did it to be sexy... And it worked.

Like a complete moron I asked, "You want my tongue?" It was the most obvious thing ever but I didn't want to be bad at this. She nodded emphatically and pulled her thong to the side. I got down there and dove right in before I let myself think about it. My tongue was all over the place. No idea what I was doing.

But, it worked. She was so incredibly wet and I was intoxicated immediately. I went to town on her. She clamped her legs around my head and was squeezing my head so tight. She screamed as she came. Hard and loud. I still couldn't believe this was happening.

Having never done that before I thought, "What now?" Before I could think anymore about it she grabbed me and started making out with me hard. She didn't care where my mouth had just been, in fact, she seemed to like it.

We made out for a while and she said, "What do you want?" I didn't know what to say. This girl I'd been obsessed with was asking me how I wanted her to make me cum. I said, "Whatever you want." She said, "Oooh dealers choice..."

She told me to lie down and pulled my jeans and boxers down enough where I was totally exposed. I had so much precum everywhere. She laughed a little and said, "You didn't cum did you?" I said no, no.. just turned on.

Ashley laid down next to me on her side and put her right hand on my dick. She was stroking it slowly. I closed my eyes and I could feel her eyes staring at me watching my reaction. "You've had a thing for me for quite a while, huh?" I nodded and asked, "Someone tell you." "It's not like you hid it well... Or tried to. I'd see the look in your eyes when I was with another man and how you'd avoid me."

I didn't have a clue what to say now. I said, "Yeah, I've had a thing for you for quite a while.." She said, "And here I am with your dick in my hand. Aren't you lucky?" We both chuckled a little. I had opened my eyes some and she kept talking.

"You are sexy and I think you have no idea," she said. I was so happy to hear her say that. I was so turned on but was getting so frustrated. I told her thank you but she was the sexy one. I moved my hips some in a desperate motion because she was going so slow. I didn't realize how much she was enjoying teasing me until later.

When I moved my hips she said, "You ok?" I said yes but she could tell I was losing it a little with my blue balls and how slow she was going. She kept talking, "Your dick is really cute." I went "Ouch. Cute huh?" She laughed and said, "No no, I mean a good looking dick." I thanked her and we laughed a little. She had moved her hand to the underside of my dick and was rubbing one finger under the head of it. I was twitching.

She was staring at me and loving it. She then went back to giving me a hand job and gripped it hard. She went at it and I blew my load everywhere, and I mean everywhere, within about 15 seconds.

She laughed and couldn't believe how much I came. We got cleaned up and I took her back to her place in a little bit.

I remember driving back home and wondering what had just happened. Was this a one time weird thing that would ruin our friend group or the best thing that has ever happened to me.

Thankfully, it was the latter.