describe your last time in pussy

Just today. With lidocaine spray to make me numb and 2 thick condoms, to avoid any sensation and to not cum. I still came and won't be allowed to piv anytime soon. She couldn't enjoy piv due to lack of hardness anyways. . I'm a big disappointment as usual.

 

Can't remember. I've been pussy free for about 10 years after divorce. I've been in mostly permanent chastity for roughly 7 years. Currently 24/7 for for over a year and no beta cummies for over 4 months. I'm going for permanent 24/7 Chastity and annual ruined orgasm in cage while plugged!! I'm self locked. Pretty much total denial except slapping my Pathetic beta balls while caged!!!

 

Roughly 5 weeks, 6 days, 19 hours and 54 minutes ago… can’t be exactly sure. Not really counting.

It was my last time but filled with a few firsts;
First time we’d had sex directly after a short period of chastity. Normally it would be cantered around other things.
First time still in a base ring. I’ve never even had a cock ring before. Never needed or understood why.

It started typically with a massage. Before she rolled onto her side holding her wand between her legs so I could enter her in a spooning position. 9/10 this was the standard routine. This time with my cock harder than usual, I could feel the contractions as she came to orgasm around my me. The feeling of her walls contracting after. Bliss.
Apparently it’s harder to cum with a ring on… so we moved to the standard missionary position until I finished.
The end…

 

It’s been so long it’s hard to remember but on the rare occasion we have PIV sex about 1-2 times a year, I will cum while I am still sliding in for the first time. Its so more intense and amazing when you only have one or two orgasms a year. She always plays and cums first. Usually multiple times. She loves me to get between her legs and play with her tits with one hand while I ram a warm thick glass dildo into her pussy at lightening speed. She uses her hitachi magic wand on her clit while I’m doing this for her. She’s well stretched out by the time she’s done cumming and let’s me know she can’t feel me when I enter her.

If she doesn’t want my mess in her she’ll hold a Fleshlight above her pussy and encourage me by telling me to fuck my girlfriend, fuck that pussy, and tells me to fuck faster or slower.

About every other time, she makes me use numbing cream and a condom so I can’t cum when I fuck her or the Fleshlight. Or course she gets her orgasms weekly with my assistance and without ever letting me out of my cage.

 

For the records, she rode me again 3 times since the day I described above (2021-04-03). But it’s been 8 months and 20 days since my last. I did cry that day on December 4th 2021, 263 days ago. Tears were in my eyes.

She let me fuck her (with me on top and thrusting my hips) 627 days ago on December 5th 2020. I didn’t last. It took 20 seconds.

I haven’t had stamina to last inside her since 2016 Sep 16th, nearly 6 years ago.

This was her decision. She encouraged me to cum quick, and trained away my stamina… with slow gentle stimulation. I had been proud of how long I could last. My fantasy was to fuck indefinitely with perfect control… and she had no interest in that.

This is what she wanted.

 

I can’t remember, i think 4 years at minimum I expect 6 years (I just turned 36). Unfortunately i’m pretty sure i got limp within a minute, my persisting impotence/size became an issue.
I kinda feel my Gf became sexually monogamous to her lover nowadays, but i’m afraid to ask.

 

Quick

 

It was February 24, 2018. My wife had been shaming and guilting me for about 6 months about how God wanted me to get her pregnant and I wasn't fulfilling my duty to God. I was really close to my breaking point with gender dysphoria at that point (I nearly ended my life a couple of months later) and had wanted to be done using my penis for anything. She finally broke my will and got me to do the act. She ended up getting pregnant, and that was how our 6th kid came into the world. It was such a traumatic experience for me that after he was born, I hated even seeing him or being in the same room as him. I'd have panic attacks being around him. It wasn't his fault and I felt terrible about it, but I just couldn't handle seeing him or being around him.

And that was the story of my last time. A couple of months later, after my failed suicide attempt, I decided to try to keep living and transition. I started HRT, and eventually lost most erectile function, and later had orchiectomy surgery which definitely removed any potential for future penetration with my penis. I don't miss it.

 

In your photos you have such a lovely smile and a contented look on your face (and you're a very beautiful woman, by the way). I really hope that this means that you've found some peace and a path that will lead you to happiness.

 

For the most part, yes, I have. Life isn't perfect now, but nobody's life is. And thank you for the kind words. I was really convinced that I would make an ugly woman, but figured it was better to be an ugly woman than a man that hated even existing. Fortunately, transitioning was very kind to me and I wound up looking pretty decent. I have insecurities about various parts of my body, like most women do, but overall I feel much better now.

 

Congrats to you! That must’ve taken incredible bravery.
And you are a very beautiful Woman; as the last poster replied.
It’s so powerful, the emotions and feelings.
I have never seriously believed that I’d like to live day to day as a woman.
But I do like to dress as one if I have a chance, and I do fantasize about it, albeit only on a sexual level.
This is not nearly the same, but it gives me the insight to know that it’s a very fine line, so fine that it doesn’t surprise me that many folks would rather end their life than endure the hardship that transitioning can be.
I’m glad you’ve come out the other side of that, and I hope you have found peace. In your pictures, it seems like you have.
You have amazing strength and I envy your courage!

 

Don't remember

 

@Shepherdsflock im glad that you are more happy now and did not do suicide.

 

I guess I'm luckier than many, and had sex with my wife a little over 9 weeks ago. Did I think I was going to go over two months without sex? No; but it wasn't unexpected. Since we've been together, the time between sex has continued to grow. This period is the longest by far however, as previously we had sex about once a month. The primary issue is squarely on me; a smaller than average penis, and a limit amount of stamina. Do I think this is the last time I'll have sex... No, but one never knows what the future brings.

What was it like? It was a typical performance for us. We cuddled, kissed, and touched each other for a time. When she was aroused, she laid on her back and entered her. She rubbed herself as I pumped for almost two minutes after which I came and got off her. She took out her favorite toy, and pleasured herself while I watched until she finished.

How do I feel about it today? Honestly, I know I'm never going to be someone who satisfies her in the bedroom. While the humiliation I experience at the time later pleases me, I feel bad she has to bother with it. Someday I think I would like for her to decide it's no longer worth the effort, and to deny me for good. I just hope that wasn't the final time; I want to experience and apricate the feel of her once more. Then again, maybe knowing the the next time will be the final time is worse (too much pressure).

 

14. 8. 2004
With a prostitute (call girl is a better word, she was pricey). After a good dinner in the restaurant (i paid too) we drank a wine in private. Then we went into bedroom and bed. I changed my mind and didn't want it. But she has other meaning (said she didn't have it for a few days) so she used a rubber on me a climbed on top of me and fucked me. (I remember she moaned what I found ridiculous - I have a small penis). After that I cried, probably because I realized that's the only sex I can get in my life (paid). She didn't hear that. Then it was over.
I don't remember how her pussy felt at all. And no, that time I didn't know it's my last pussy, I wanted repeat something like that (a prostitute) at least after five years (my first sex - paid - was five years before this), but I didn't make it, nor after ten years... I will probably stay pussy free for the rest of my life...

 

I swear to God I am not lying or saying this to get off as part of the fantasy. But I genuinely can't get off from normal sex at all. I'm an average looking guy and had a few GF's and I promise I've cum inside a woman less than 5 times in my life. Usually, I get fed up pull it out and beat off and the girl feels awful. She thinks there is something wrong with her and there isn't its just that it doesn't do it for me.

I wondered if I might be gay and spent half an hour going through clips on the gay side of Pornhub which confirmed it wasn't. I felt like an idiot for not realising that I had happily jerked off to millions on women in porn. lol

 

It has only been two weeks since last time. My Queen released me with a cage and jerked my dick upright. I had to grease my Queen's anus at first. I was able to insert the glans – into the lovely wet vagina – but only the glans. Then out and after that I was able to push into her tight anus. My queen set the clock on—I had two minutes to launch into her tight hole. Fortunately, I managed to do it – there was time left. This is so rare that there was no need to wait for an orgasm. After this, I was able to satisfy Her with my mouth. Take a shower and lock the cage.