It started simply enough.

  • Thread startersissycuck9
  • Start date

sissycuck9

New around here...
Beloved Member
Oct 8, 2006
26
3
8
One night after sex, Jen asked as she laid beside me; "I wonder what it would feel like if it were bigger". "Huh?" I mumbled, feeling nervous. "Well, it's just that, well, I can barely feel it down there when you're inside me." I was really getting nervous now. "What do you mean?" I asked, not knowing really what to say. "Well you've told me yourself that you're not really huge down there, and I just wonder what it would feel like if you were, well, if it was bigger. I love you, I just, umm, wish I could feel it more."
"I'm sorry honey, I don't really know what to say."
"Oh it's okay, don't worry about it."
But it wasn't okay, and I knew it. I had to do something. A week later I ordered a strap-on dildo (nothing huge, but giant compared to me). And that was the mistake that changed my life forever.
That first night when I tucked my own penis down to make room for the big piece of rubber was amazing for Jen, and very humiliating for me. As I entered her with the dildo, she gasped and her eyes opened wide. She'd never been filled up like this before. And I have to admit, I was pretty impressed myself as I watched her pussy stretch to swallow the bigger shaft. I only pumped her for a minute or two before her body became taut and she started to scream an orgasm. I had to bring her to two more before she let me take the dildo off. I was so horny. I couldn't wait to get inside her. But as I slid my little member into her, she started to chuckle. I knew it was because she couldn't even tell I was inside her. I was stung with an incredible shame. She tried to stop giggling, but she couldn't help it. And I couldn't help but start to cry. But I kept thrusting. I was so humiliated, but still so horny. I had my little orgasm as tears crept down my face and Jen tried to hold back from laughing.
We didn't use the dildo again for a while. But when we made love, it was easy to see that she was bored but pretending as best she could.
Finally I caved. I knew I had to. I used the strap-on again, and again she came to incredible orgasms as the replacement penis thrusted deep inside her. This time, to avoid the embarrasment, I just knelt over her and masturbated onto her stomach.
She didn't laugh, but it was still humiliating.
This routine went on for almost a year. It was awful for me, and I knew that I'd lost Jen's respect. I couldn't live like this. I knew she deserved to be with a real man, not having to imagine that the piece of rubber inside her was a real penis. And so finally I worked up the courage to tell her what I knew I had to. "Honey, listen. I know that it's not fair for you to never be able to have a real penis inside you. I mean, I hope you're still enjoying the dildo, but I just want you to know that I think you should get to be with a man who has a bigger penis than I do. I, I still want to be your husband, and I don't want to leave, but I want you to find another man who can give you what I can't."
"Are you serious?", she asked.
"Yes Jen, I am."
She didn't act on my offer for almost three months. In fact, we didn't even discuss it.

"I met this guy at work."
I knew it was coming, but nothing could have prepared me for hearing her say that.
"He thinks it's kind of weird that I have a husband, but he's okay with it."
I couldn't help but be crushed.
"If it's okay with you, I'm going to spend the night with him."
My world was spinning, but I managed to mumble my approval.
Watching her get ready was incredibly humiliating. She spent nearly two hours perfecting her makeup and outfit. When she walked out the door she looked incredible; a sleeveless, lowcut shirt draped down to just a few inches above her tight-fitting jeans, leaving just a few tantalizing inches of ******* skin above the low cut waist. Her hair and makeup were perfect, and the heels she chose gave her bottom an enticing wiggle as she walked out to the car.
I didn't get a kiss goodbye, she just waved as she excitedly got into the car. And then she was gone.
I masturbated all night. I would go to sleep, only to wake up an hour or two later. I would masturbate again, then cry and go back to sleep.
I didn't get to see her the next morning before I left for work. But I couldn't stop thinking about her with another guy, and I went to the bathroom every few hours to masturbate.
When I saw Jen that night, I knew right away that being with other men wasn't going to be a temporary thing. She was glowing.
That night she let me have intercourse with her - no dildo involved. It was to be the last time. This time she didn't laugh. She just looked at me with pity now, obviously unable to feel anything that I was doing.
Her visits with Dave started becoming more frequent. And I developed a habit of masturbating two or three times a day, which bothered Jen a lot.

"I wish you wouldn't always be masturbating honey, it's so immature."
"I can't help it, I don't have any sex anymore." I replied.
"Well I just don't think it's good for you."
A little research on the internet later, and a pink CB-3000 was on it's way.
I still remember the first time I snapped the lock shut. She had already hidden the key. I felt a sinking in my stomach as the realization of my new predicament settled in.
We hadn't really made a plan for when I would be allowed out of it yet. After some heated discussion (and a reminder that only she knew where the keys were and I'd better settle down), it was decided that I would be allowed to masturbate only when she was with Dave.
I could never have imagined the frustration of having my penis locked away after having grown accustomed to masturbating several times a day. I would beg Jen to let me out, but it was no use. I started to look forward to Jen's nights with Dave more and more.
 
The saying
"Be careful what you wish for..... you may get it" comes to mind here.

I would be interested in hearing further developments in your relationship.
I forsee some interesting things in your future.

A hot retelling though.
 
I also am very interested in reading more.
 
Love to hear more!
 
i wanna hear more to. how big is Dave? Does she cum home with a filled pussy for you to lick? lets hear.....