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04/11/2021 12:50 am
Hello gentlemen.
My wife and I have taken things to the next level in my prostate journey. After a really great joint masturbation session,where she learned that males can indeed multiple orgasm,and orgasm as powerfully as women,she suggested trying pegging as a way to be actively involved in my prostate pleasure and resulting orgasms. Foreplay exploration since, has been very prostate focused and sex supercharged as new avenues of pleasure open up to us as a couple.
This weekend,she finally deflowered me. She mentioned during the day that we’d be having some fun that night. I knew what it meant. I’d kind of let any reservations I had go. Decided to just man-up and take it lol. After all,with the things I’ve learned so far on my journey,how bad could it be? We spent much of the day in the garden,couple of glasses of wine and what not.
Wife spent half the day flirting,flashing her breasts at the most inappropriate times,and was clearly excited for what was to come.After all,she’s been planning this for a couple of weeks.
Not long before bed,she ran us a hot bath,which we took together. We took turns to wash each other,and then from behind her,I washed her hair. She’s always loved me washing her hair,we both love the sensuality and intimacy of it. We were relaxed and starting to get really horny.
Once in the bedroom,we laid down on a large throw she had already laid out,obviously she had safeguarding her precious bedding in mind,incase things got dirty ha ha.
We began with a little normal foreplay consisting of kissing and some mutual exploring. I didn’t want her missing out too much,so i went down on her. I could tell she was already buzzing as I watched her massage her breasts and nipples as I tongue punched her ham wallet. She does this when she’s really turned on. She orgasmed quite quickly,then i moved to fingers only until she came again in quick succession.
She rolled me onto my back,saying that’s enough for now,tonight is for you.
She poured herself some lube and gave me a teasing testicle and perineum massage. Every so often,she’d go down and circle my anus,she had that knowing smile again,I’m not even sure I knew I was being guided along. Soon enough,when she’d circle my anus,I’d lift my hips slightly,trying to get her finger inside. She happily obliged. Her hand was well lubed,and she slid in easily.
She’d slipped a finger in at various times over the years,but it was only to be naughty,it was never prostate focused before. I relaxed myself as she made her way to my gland. Funny enough,she found it straight away,and began to circle it and stroke it up and down. It felt really good this time round. I was soon floating like I was on an inflatable in a pool. I was vaguely aware of how she skilfully manipulated the speed and pressure of her stroke,not too hard,nor soft. It was spot on. She could have been forgiven for asking why men can’t get this right first time! Then she’d reach past it,and drag her finger down past the gland,and repeat,it was heavenly. I got busy with some nipple diddling and started to have some gentle orgasms,i felt a little sleepy i was so relaxed. She continued to stroke herself with her free hand. They just came in little waves in sync with her strokes. Every so often I’d ‘come to’ a little,when I’d feel the tip of her tongue skate over my urethra opening to collect some of the pre cum that was flowing quite freely.
Then,she announced playtime was over,she produced a large cock ring and told me to put it on while she got ready. It was one of them that fits over the penis and the testicles.
She left the room. When she returned she had donned a small strap-on clit vibrator,and her main strap-on with an 8 inch dildo attatached on top. I gulped lol. She then lightened things up by placing her hands on her hips and asking proudly “Do you like my cock”?.
We both laughed like a couple of kids.
She came over and generously lubed up the dildo. Then,she filled a little douche,inserted it,and filled me up.
Lastly,she added some silicone lube and that was her ready. I have to say, she was very aroused,more than me I think.
She told me to relax an she lined the dildo up with my anus and stroked the head around my opening. I was really horny,but apprehensive at the same time. She began to slowly push in. She was watching me very intently,gauging my expression for pain. And I did feel some,but nothing like the burning!! Damn,it burned. She backed of a little and gave me some time to centre myself. Then she pressed on,gently. After 3-4 inches,it got a little easier,like that point when we insert an Aneros toy,there is resistance,then,you get past it,and it just slides in the rest of the way. She stopped after about 6 inches. Then she leaned forward and we kissed for a min or two,giving me time to relax and get myself centred again.
She raised up again,switched on her vibrator,and began to saw in and out of me. I struggled a bit at the start,trying to contract my pelvic muscles,trying to run sequences that work in solo sessions,but it was incredibly difficult with her dildo inside me. So was getting erect,I was mostly flaccid,but still pointing upward which was the point of the cock ring,she wanted to see the precum dripping out. As usual she was onto things. She told me to stop trying to make things work,she would give me the pleasure,but I’d have to accept it,just to relax and give myself to her.
I took a deep breath and did a slight reverse kegel to start relaxing things and then just let everything go. I focused on her,she looked really sexy. Her breasts rocking back and forth with her thrusts,and that wide eyed horny look on her face,it was very erotic. The pleasure waves began to flow,and for the first time,I started to enjoy myself. She asked me did I like it and I confirmed it,she said with a cheeky smile that she knew I would.
Then she started in with the naughtier chat. She said I looked really hot getting my ass fucked. She asked me did I want to see her ass getting fucked while I stroked my cock and prostate. Or that we could mount the toy and ride cocks together. Let myself down again,I had the makings of an erection. She shook her head smiling. “I know you better than you know yourself dirty boy”. “I want to see you cumming on my cock”. I was a little embarrassed and aroused simultaneously,she was in her element. I’ve noted she’s really getting into this cuckoldy type of sex talk.
Precum started to drip out in a pulsatile manner as a pretty strong orgasm washed over me,setting her off in turn,and her eyes rolled up as her own orgasm hit,she moaned coming down off her orgasm,and said that this was really doing it for her.
She started to pickup the pace a little and after a couple of minutes I came again,and so did she. At this point,I was in a haze,I didn’t even care anymore about whatever I’d worried about previously. She had become maybe the most aroused I’ve ever seen. Wide eyed and a bit wild. I had 6 big orgasms in all,and she matched each one with her own. Then I started to get a little chaffed. She withdrew and got rid of her strap-Ons.
She grabbed the lube and generously lathered my penis. I thought she was going to finish me with a TO. She then stood up,and squatted down,and positioned my penis against her own anus,and dropped down all the way in one go. She shut her eyes and gasped. I wondered if she’d regretted it lol. She opened her eyes and started to bounce on my penis. The eye contact was rather aggressive on her part,she was still really turned on. Maybe it was all the orgasms,but I strangely felt that ejaculation for me was rather far away.
She continued to bounce,getting more and more worked up. She stood up about half way,furiously worked her clit and squirted all over me,I noted she looked almost angry. All I could get out was “fuck yes!”. She squatted back down and began to bounce on me again.I’ve never seen here behave in such a dominate way,but I can’t say I didn’t like it.
My arousal was on the way back up and I told her I was going to cum soon. She squealed her approval and bounced all the more and straightened up little and started her clit work again. I told her I was nearly there and our grunts synced up. When I started to ejaculate,she came really hard,squirting again as she bounced. She kept going until she’d drained every last drop from me and then finally she stopped. Then she flopped off onto the bed,still panting. I noticed from her midriff down to her feet was shuddering and she was still panting.
I asked her if she was ok,and she said she was,she just had sex shakes,and that this was some of the best sex we’ve ever had.
She told me in pillow talk that she’d loved the evenings fun. And that it wouldnt be the last. She said she’d really enjoyed having a dick and that men are lucky. She really enjoyed exploring her dominant side too. Her only gripe was that she couldn’t cum inside me. She also said she was going to shop around for some new things to play with in these sessions.
In summary,I have to admit,once I got into it,I really enjoyed my first pegging. I had some big orgasms,but I don’t think they were super-super o territory. But I hope to get there eventually. I sure hope it’s on the cards a few times a month now. I’d definitely recommend it to any guy. It’s completely different to what we are used to. Maybe that’s why it’s so good.
04/11/2021 1:32 am
@Helghast , Congratulations 
on losing your cherry and getting over your reluctance factor, it sounds like the two of you had a great time. Thanks for sharing your very erotic adventure, I'm hopeful it will help other men on this Forum overcome their own trepidation at exploring this sexual option. It would be wonderful if your wife could add her perspective of the event as well.
Good Vibes to You!
04/11/2021 1:53 am
Sounds like a steaming heap of fun! However... next time, collect at least some of that precious squirt in the ceremonial silver chalice, look her in the eyes and mutter how much you love her between sips like a good boy. If this makes her cry with joy, kiss every single one of her tears off her cheeks and place them on her lips. (Kidding, not at all kidding.)
you said it burned... good luck finding a lube that works for you. Pure silicone is the best but no good for silicone toys. This is my biggest problem, and my partner’s problem as well. As for chafing at the end, many of us have limits. I don’t know how they do it in pornos, if it requires huge amounts of line, or if the receivers just grin and bear it for the money...
You said you weren’t in “super-super o territory”. Maybe it is because you are searching for what you previously defined as a super o. Qualitatively, orgasms can be as vast as we let them be. I am sure that as you continue your freeform lovemaking, you will redefine again and again what an orgasm is, and soon you will be the one shaking on the bed, with your wife asking if everything is ok.
Topic starter
04/11/2021 6:07 am
@rumel I have asked her if she wants to say something and she is mulling it over! Don’t think she’s quite sure what she’s supposed to say.
Topic starter
04/11/2021 6:51 am
you said it burned
I’ve used it before with the helix,wasn’t the lube,it was pain!! Haha
Maybe it is because you are searching for what you previously defined as a super o.
Yes I suspect you are correct. A little more relaxing and opening up required!
04/11/2021 7:45 am
@helghast, congratulations on your quite exciting adventure! Reading your story is a turn-on, I can just imagine being the player receiving the treatment.
@ruby-ryder would be proud of you both!
Topic starter
04/11/2021 8:27 am
However... next time, collect at least some of that precious squirt in the ceremonial silver chalice, look her in the eyes and mutter how much you love her between sips like a good boy.
Your mind is in the gutter... but I like it.
Really I’d have liked a squirt in the face,but she had her own ideas,she was off in la la land. But I’ll get it some day! She was like a bitch in heat,I’d swear she was marking my genitals as owned lol.
Topic starter
04/11/2021 8:29 am
@ggringo one of the best nights of my life,I could hardly sleep I was so excited! I can’t wait to do it again. As long as it gets better and better,I’m in!
04/11/2021 1:23 pm
. As long as it gets better and better,I’m in!
Keep us in too! LOL
04/11/2021 9:21 pm
She told me to relax an she lined the dildo up with my anus and stroked the head around my opening. I was really horny,but apprehensive at the same time. She began to slowly push in. She was watching me very intently,gauging my expression for pain. And I did feel some,but nothing like the burning!! Damn,it burned. She backed of a little and gave me some time to centre myself. Then she pressed on,gently. After 3-4 inches,it got a little easier,like that point when we insert an Aneros toy,there is resistance,then,you get past it,and it just slides in the rest of the way. She stopped after about 6 inches. Then she leaned forward and we kissed for a min or two,giving me time to relax and get myself centred again.
She raised up again,switched on her vibrator,and began to saw in and out of me. I struggled a bit at the start,trying to contract my pelvic muscles,trying to run sequences that work in solo sessions,but it was incredibly difficult with her dildo inside me. So was getting erect,I was mostly flaccid,but still pointing upward which was the point of the cock ring,she wanted to see the precum dripping out. As usual she was onto things. She told me to stop trying to make things work,she would give me the pleasure,but I’d have to accept it,just to relax and give myself to her.
I took a deep breath and did a slight reverse kegel to start relaxing things and then just let everything go. I focused on her,she looked really sexy. Her breasts rocking back and forth with her thrusts,and that wide eyed horny look on her face,it was very erotic. The pleasure waves began to flow,and for the first time,I started to enjoy myself. She asked me did I like it and I confirmed it,she said with a cheeky smile that she knew I would.
Then she started in with the naughtier chat. She said I looked really hot getting my ass fucked. She asked me did I want to see her ass getting fucked while I stroked my cock and prostate. Or that we could mount the toy and ride cocks together. Let myself down again,I had the makings of an erection. She shook her head smiling. “I know you better than you know yourself dirty boy”. “I want to see you cumming on my cock”. I was a little embarrassed and aroused simultaneously,she was in her element. I’ve noted she’s really getting into this cuckoldy type of sex talk.
Precum started to drip out in a pulsatile manner as a pretty strong orgasm washed over me,setting her off in turn,and her eyes rolled up as her own orgasm hit,she moaned coming down off her orgasm,and said that this was really doing it for her.
She started to pickup the pace a little and after a couple of minutes I came again,and so did she. At this point,I was in a haze,I didn’t even care anymore about whatever I’d worried about previously. She had become maybe the most aroused I’ve ever seen. Wide eyed and a bit wild. I had 6 big orgasms in all,and she matched each one with her own. Then I started to get a little chaffed. She withdrew and got rid of her strap-Ons.
She grabbed the lube and generously lathered my penis. I thought she was going to finish me with a TO. She then stood up,and squatted down,and positioned my penis against her own anus,and dropped down all the way in one go. She shut her eyes and gasped. I wondered if she’d regretted it lol. She opened her eyes and started to bounce on my penis. The eye contact was rather aggressive on her part,she was still really turned on. Maybe it was all the orgasms,but I strangely felt that ejaculation for me was rather far away.
She continued to bounce,getting more and more worked up. She stood up about half way,furiously worked her clit and squirted all over me,I noted she looked almost angry. All I could get out was “fuck yes!”. She squatted back down and began to bounce on me again.I’ve never seen here behave in such a dominate way,but I can’t say I didn’t like it.
My arousal was on the way back up and I told her I was going to cum soon. She squealed her approval and bounced all the more and straightened up little and started her clit work again. I told her I was nearly there and our grunts synced up. When I started to ejaculate,she came really hard,squirting again as she bounced. She kept going until she’d drained every last drop from me and then finally she stopped. Then she flopped off onto the bed,still panting. I noticed from her midriff down to her feet was shuddering and she was still panting.
I asked her if she was ok,and she said she was,she just had sex shakes,and that this was some of the best sex we’ve ever had.
what a great story. Conratz! I envy you a bit, haha
that's my favorite part!
This post was modified 4 years ago by [email protected]
04/12/2021 12:22 pm
first of all thanks a ton for letting us take part. If I were a smoker, I'd need a cigarette right now. Phew!
What a hot night, what an awesome hot wife!
From my own experiences with the "real thing" I can disclose to you, that I've mostly felt pain at my second sphincter during his first penetration too - until I finally learned that only a quarter turn to the right already made things much easier for me. When he kind of screwed his member in I suddenly felt no pain anymore and could focus on and give in to that wonderful filling feeling only. 🙂
After all you leave me drippin' in anticipation of your next reports.
Cheers! Mart
04/12/2021 12:35 pm
Your mind is in the gutter...
You don’t know the half of it 🙂
Topic starter
04/12/2021 12:39 pm
I've mostly felt pain at my second sphincter during his first penetration too
Devine o mentioned the second sphincter too,that must have been it,everything loosened up after a little bit,I’m sure it can only get better.
That was wife’s only gripe,that she wasn’t in possession of the real thing,she wanted to ejaculate haha She reckons boys are lucky to have penises. She’s quite funny,she said to me. “I wish I could have a real dick that I can clip on and clip off,I’d shag lots of people with it”. She’s nuts ha ha
04/12/2021 12:52 pm
She reckons boys are lucky to have penises.
Tell her, that I instead reckon girls who are lucky to have vaginas and that I myself only lately got a bit closer to what that opportunity would perhaps mean to my sexual world view. Submitting to a few hypnosis sessions reflecting on gender transformation and making a man envision how it would feel to have a pussy, my last encounter indeed left me kind of frustrated about not being able to ever feel a double penetration the way a woman can. Perhaps this idea might soothe her a bit or eventually give her new ideas? 😉
Good vibes and even more orgasmic pleasures! Mart
Topic starter
04/12/2021 1:05 pm
@sowithoutaneros safe to say she enjoyed “playing the guy”. I’m quite certain she enjoyed the night more than me! And I really enjoyed. Can’t wait to do it again.
Totally agree,women have all the luck ha ha. She’s got ideas,that’s for sure 🙂
Topic starter
04/12/2021 11:11 pm
@runinnekidgmail-com yea we will keep her around lol
04/13/2021 8:43 am
@Heighast: I am amazed that your wife would choose an eight inch dildo for your first attempt at pegging. If the girth matched the length of such a tool, no wonder you felt a burn.
Was this pay back to you on your anatomy and the years of her handling such an endowment? If not, she sure went for the gold in a dildo of that size for your first jump into the water.
Amazing. Thanks for sharing such an intimate side of your marriage. This will probably never happen in my marriage so it is good to be able to see your journey detailed here.
Topic starter
04/13/2021 8:55 am
@turnrow Alas! Wife thought it through. I was on my back for this,her on her knees. The 8 inch was for reach. She wanted to be able to get to my lips and nipples without popping out. I guess I should have included,it was not a large diameter dildo,below the average girth I believe. So don’t panic just yet 🙂
And yes,I was teased relentlessly,with the old “let’s see how you get on” and “aww it only hurts like a bitch the first time” lol
04/13/2021 12:25 pm
And she had asked him before ... so what! 😉
When the going gets tough, the tough get going! 🙂
After tonight, he’ll be the one begging for me to take charge ~
Topic starter
04/13/2021 12:31 pm
@sowithoutaneros You know exactly how it is Mart hahahaha That view brings back some memories!!!
Im getting excited 😉
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