I was raised up rather protected sexually. My fiancé was too. When we met, I was somewhat more experienced than she was. That first time we met, we had intercourse. Her expression on her face said it all, a mixture of shame, love, trust and fear. She was a bit disturbed and confused but very proud and fulfilled. How was I to know about my pegging fantasy in the future and my wife would peg me!
I got married a year after we first had sex and my relationship with her was very satisfying. My wife and I began to overcome all of the embarrassments that had been bothering us that previous year. I had what I thought was a successful marriage, complete with two children. On the job side, my wife became much more assertive, confident and successful.
Things became different in bed too!
My wife began to be more assertive and more enthusiastic to have a great time sexually. More often than not she took the position on top. A year ago she would even giggle at my efforts to give her oral sex. She began to love what she was previously embarrassed for me to do.
It was shortly after that she brought up the idea of having anal sex.
She had been to a bachelorettes party. One of the ladies said she had been doing it with and to her partner. And it was really great at equaling their relationship. I was really frightened, to put it mildly.
Visions of being gay ran through my mind both to give it to her. But more at the thought of receiving it. My wife assured me that I was not nor would I ever become gay. But I tried my level best to let the topic die a natural death.
She would not give up on the idea of Pegging
Every now and then she brought it up. Eventually she invited me on a date to meet for dinner. And then go to a some sex shops to explore the different sex toys and aids available that would ultimately spice up our sex life..
My wife and I had a marvelous dinner in Ramsgate and then after went and to the adult lifestyle centre in Kogarah. I was amazed at the many collections of adult toys available. But my wife took me over to the strap on section and particularly at the pegging sex toys that were there. We both chuckled and I found myself accepting how normal this seemed to be. Starting with declining all the pegging toys shown to me to starting to say, ‘No, that one’s too large’.
Finally we found the largest range of strap-ons
We had come across in the store and found a harness with a dildo that was on the smaller side. But still seemed to me bigger than a barnyard. We settled on this one and purchased it. My wife was so excited. Where I was more nervous and agreed that this was a special Friday night that I did not want to spoil. So would do the deed on Saturday night.
Saturday I was nervous
My wife was whistling and singing without a care in the world. It was like she had taken off ten years, whereas I felt ten years old. Soon evening came and we took the children safely to the baby-sitter’s.
When we returned home we took our clothes off and caressed, kissed and then took a relaxing bath with lovely candles and scented bubbles. As we got out of the bath my wife handed me an anal douche and reality struck me that my virgin ass was going to be penetrated.
I did what I had to do and was anally cleansed. Walked slowly to the bedroom where my wife was waiting in a very sexy negligee.
My Pegging Fantasy
Our room had ambient music, candles were lit and in all other aspects it was romantic and soothing. But I realized now we were set to go. I looked at her.
“Are you done?” She asked me.
” Yes honey, everything squeaky clean,” I answered.
I could not believe I was going to do this. Hesitantly I took myself over to the bed and lay down. She went over to our dressing room closet and was gone a few minutes.
When she returned was fully harnessed and I think I must have gasped. The vision of that projectile protruding from her brought everything home. It was real.
I was just about to be ass fucked.
She smiled at me, sensing my anxiety. “Don’t you worry honey,” she said. “There’s’ nothing to fear.”
She was now on top of me, pressed the tip of the dildo to my face and told me to lube it up. Shaking however I put on as much as I wanted. I did it exhaustively. She then got up, went over to the hi-fi and put on a new track, turned it up really high, and then came back into bed.
This is just the beginning of how I was going to get pegged!
We had talked about this moment for some days and I remembered all the rules. Resist the urge to tighten up, be calm, relax and it will fit fine.
“Fine, honey,” she said, “all is ready.”
I lay on my back, spread my legs as wide apart as I could and raised my bottom up into the air. She made a sigh and the next thing I sensed was the dong feeling sticky. Rubbing up against my middle thigh and balls and around those areas.
In hindsight this was really funny as my wife was totally an amateur with harness and dildo and using it clumsily. At that moment I froze feeling her uncertainty. Making my own fears and trepidation’s greater. This did not appear to be going according to plan.
“Honey, it is not going to work out if you are so afraid,” she said. “Just relax ease back.“
I tried to as she had guided the head of the dildo with one of her hands.
Next thing I knew and felt was the tip of it touch my anus. Then slowly it began to enter.
This time again I tensed up and it felt very horrible and painful and I cried out. She then withdrew and said relax. And rubbed the back of my thighs and ass cheeks. Quietly without my knowledge she applied a bit more anal lube. Gently, she rested the dildo to just outside of my anus.
“Please try again honey,” she said, “believe me it will be fine.”
I did exactly that and began to swivel my hips and groove to the music. I put my arms back down again. Got lost in the tune, which was thrashing and very loud. I pushed back but this time I did not resist at all.
Slowly, gently the dildo pressed in and all of a sudden it just slid inside.
I gasped and groaned.
“Oh my goodness,” “Mmmmmmh!” she said, “Here is more honey.”
With that, she inserted the full length of that strap on dildo inside of me.
Another “Oh my God” from me.
Then the pushing began. “Keep with me babe,” she said.
I tried imitate what she had done for me hundreds of times whilst having marital sex. Bucking my hips up in pace to meet her stabs. I could not believe it. All my life I thought I had been and would be the perpetrator even when my wife was more aggressive.
Now I was copping it up the ass.
I knew that there was no doubt as to who was doing what to who. Now as the one being penetrated, I was on the other side. She had gotten her way to give it to me and me give up my anal virginity.
She had thrusted, probed and done other kind of things. All to her own point of view and without much concern as to what I really wanted. She had been the one in control, self-assured, cool. While I’d been afraid, out of control and emotional.
To say I did not enjoy it would be a lie.
I had a great and intense orgasm. My mind had whirled at the experience; and my body had been elevated and enjoyed almost every second of it. Even the pain that I had felt at the start was rewarded in the end by pleasure. A
fter orgasm I became emotional and started to cry. I told my wife all these things. And opened up to her as she had to me on many occasions when I thought I had been making love to her. But now knew that I was just exercising my physical dominance over her.
She had loved being in charge from the look of things for a change and how good it felt to be in control of things, very different to usually being under control. What really amazed her was how protective she had become of me when she noticed that I was now defenseless and vulnerable. She felt like she had conquered me. But at the same time wanted to protect me and make sure I was alright.
After all, I’d just done what she wanted me to and surrendered my virgin ass.
She pegged me and I liked it!
She Pegged My Ass!
For those of you who don’t understand what is pegging, its a neologism made by all-around-wonderful fellow Dan Savage., It fundamentally includes a broom handle, somel tape, and a man and lady who need to zest things up in the bedroom. But couldn’t pay for a strap-on.
This is my story of how she pegged my ass for the very first time.
I’m really a gentle fellow who is aroused easily at a basic level. And that had reflected what I did and tried in the bedroom. I used to think to myself,
“the more gentle I am with my partner and the more I accommodate them, the more they will want me!”
If you’ve never pegged before its an experience that is both startling and extraordinarily thrilling.
My first occasion I was pegged it was with a young lady named Doris who had acquainted me with an entire host of new ways to approach sex.
Our first date was a thing of wonder when I discovered that she was into the BDSM lifestyle. And was a domme that liked to take things to the extreme. When I woke up the following morning from said date, I really needed to let my flatmate know that I was okay and consented to the previous evening. As welts and bruises were showing all over my body.
That previous night I had been stomped, kicked, smacked, spat on and pretty much everything else you can imagine whilst being humiliated.
The funny thing was I had liked it.
In fact I loved it and I could not wait till the next date when my new mistress would come again. And help train me some more into the ways of the S&M lifestyle.
No scented candles or flowers for her she had told me. She was going to be harsh, cruel and insolent towards me. And if I was to see her again I was going to allow that and more.
Over the next week she taught me so many things and I began experiencing new sexual practices . Sometimes being embarrassed and frightened. But always being invigorated and satisfied at the end of our sessions. Sometimes, but not often we reversed role playing and she allowed me place a gag on her.
She also allowed me to throat fuck her until she gagged.
These were all wild and wonderful experiences I had never before had, At times she made me a human cushion. By binding my hands and feet and laying me on the couch and then sitting on me whilst she watched tv or read a book. I was not allowed to talk and interact with her until I was released from those restraints.
It was a liberating time of my life.
After two of three months into our relationship we began discussing anal sex.
I had given it once in my life to another woman. There was no way you could say I was an expert in that field regardless that I had attended FemSex classes at Sydney University.
She spoke to me about dominating me and pegging me with a strap on. An idea actually had a fair bit of appeal from my point of view. Popularity of prostate massaging in men had long sent away the stigma that men that enjoyed anal sex were all gay.
We decided that it was time to do some adult shopping at a sex toy shop to get the gear needed.
When we strolled into the Oh Zone store in Kogarah
We were met by a lovely lady who was so helpful and let us in on all the facts about pegging. My love of indian food made me query about the best enema kits. Whilst Doris inspected the strap-on and lubricant sections.
After about 20 minutes in the store we both left with our package of sex toy goodies and headed for hom.
There are things that you ought to think about before any sort of anal play. Let’s face it things can get wild. You would not want to spoil it by having a nasty surprise occur mid action.
So once we walked in the entrance-way I headed for the bathroom and put to use my enema. Using it a couple of times over 15 minutes to thoroughly flush myself out. Believe me it is time well-spent and gives you confidence and relaxes you before some anal pounding.
https://www.youtube.com/watch?v=F5A_oHVMgSg
When I left the bathroom our eyes met
We simultaneously moved towards the bedroom. To be fair I was a little apprehensive. But more excited by this new sexual experimentation into pegging. I got undressed and lay on the bed whilst she too undressed. But remained standing and began to put on her strap on that held by a panty harness.
It was a sight to be seen. Especially when you know that the 8 inch dildo is soon going to be inside your rectum.
She approached me on the bed. Whilst with her hands she began with one to stroke the realistic dildo whilst with the other pour lubricant onto and all over it. This dildo was realistic so it wobbled and swayed unwieldy with each stride.
Once she reached me she poured lube on my cock
And let it run down between my legs. Lube was fucking cold – but in a nice way. She stroked my cock that was already hard and getting harder. Slowly her hand traveled down my cock and then between my ass cheeks as she gently played around my rosebud.
This was such a turn on. I could feel my dick spasming each time her finger circled my butt hole.
She then directed me to put my face down in the pillow and my ass up in the air doggie style. I complied as she added more lube around my ass. Slowly she put the head of the dildo on my virgin hole and started to push with slow but constant pressure. Before long my sphincter muscle ‘popped’ and allowed the tip of it in.
I inhaled and exhaled as she slowly slipped the entire length of the dildo into my now welcoming ass.
It felt like I need to go for a crap during this stage. But I know that wasn’t possible as there was nothing left inside me. It was not till later that I read it is a common ‘phantom’ feeling that is your bodies reaction to having an object inserted near the colon.
She gently began to stroked that dildo in and out of me.
Heavenly f*ck. What is occurring? As she starts pushing everything starts to come alive in my body and brain. Amazement, elation, bewilderment, enchantment. Everything! How is it that MY legs are the ones open and my ass the one being now pounded?
How is it that I’m the one being fucked, and I’m seeing a couple of tits swinging at me from above? It was a complete bizarre sexual sensation.
After I have cum, she starts to pull out.
“Gradually,” I say.
“All clean,” she says happily.
VICTORY, I think.
Doris and I had a wicked relationship for about 6 months. Thereafter my relationships with women were different and I always let them know that I enjoyed being pegged. Most women are used to using their hips to accept the thrusts of me and do not put the power required to peg well.
Doris knew exactly what she was doing – I miss her still.
“Hey Eric have you made me dinner yet?” I hear from the lounge-room.
I better get this dinner sorted. Forgot to tell you – I am a cuckolded male now – but that is another story!
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