First Pegging

My "Inexperienced and Unprepared" and "Slightly Experienced but Prepared" stories are more or less the retelling of the start of mine and Hazel's love affair. We have just passed the 16

th

anniversary of our first time. When we started, we were both quickly approaching our 30's. We were both successful career-wise but neither of us had had much luck on the personal side. I had never had sex and she had only been with two men, neither of them overly long term. We were both fairly attractive but never felt comfortable putting ourselves out there until we connected on that dating site and we have been together ever since.

Since that first time, I have definitely been the one that has pushed us to try more things. First time outdoors happened a few months at my place. I was the first to forgo clothes, walking around her house naked during our love making weekends that first summer. I initiated the first time we did it in an old Bed and Breakfast in San Fran with the windows open. I was the one that had the bright idea to do it in a pool at a house we were renting. Not realizing that the water was too cold but we did warm up each other in the living room with the blinds open. On one of our first wedding anniversaries that we were able to get a babysitter, I took her breath away when I gave her analingus when she climbed out of the jacuzzi tub. She stayed in that position as I fingered her pussy and rimmed her to orgasm.

For her part she was the one that first suggested I not put on a condom and cum inside her a few months into dating. First time anyone had done that to her. She had me cum into her mouth and swallowed it without me asking for it and will continue to do that. I'm definitely the more adventurous one but she is always willing to take my hand and go with me every time.

Like every red-blooded man, I brought up anal with her and she said that it was a 5

th

year anniversary type thing. Well at the 5

th

anniversary of us dating I brought it up joking and she had to clarify that she meant wedding anniversary. So, I had to wait a couple more years to jokingly bring it up but I enjoy nothing more than cumming into her pussy while we stare into each other eyes.

As I got older my feelings towards anal in a loving relationship changed and it didn't really interest me like it once did. That all started to change after I listened to a "Mystery Box Show" on YouTube where Allison Moon talked about pegging what would end up becoming her partner. The enthusiasm that she spoke with made me do some research into pegging.

On and off for the next few months I'd look into it but never got hooked since all the porn videos I could find were mostly femdom type stuff and while I've always wanted Hazel to take the lead, they weren't what I was looking for on our first time. There was no real..... sensitivity, I guess. I continued to explore some but couldn't figure out a way to bring this up with Hazel. My fear of her reaction kept stopping me.

I figured I first needed to find out if I enjoyed having something in my ass when I came so I decided to get a butt plug and a prostate plug and try it out. With my project work, I spend long periods of time away from Hazel so she wouldn't find these toys if I never told her about them. With the lube that the lady at the sex shop recommended, the plug easily slid in but it didn't feel different so I changed it out with the prostate one. Well, when I came with that one rubbing against the taint, "wow" is all I can say. It felt like someone slapped my brain as I ejaculated. I then needed to figure out how to bring this new kink up with Hazel.

Back to the sex shop for some supplies and this time I picked up a sex question game. Even though we knew each other's histories I figured that this would be a good way to bring up any deep desires she had and never felt comfortable telling me. During our next nightly phone call, I started the game and read the first one to her. It was a fairly tame one. She asked were this had come from and I told her about the card game. We laughed, then I told her to answer. We continued on with this for the next 20 minutes. It had been as close to sexual contact as we had for a few weeks. I kept the questions light hearted but knew when I got home, we would have some fun.

Fast forward to the next trip home and I was rubbing her feet and decided to pull out the box and play. We each took turns asking questions but we both answered the same question after the other person gave their answer. I was drawing in order and going with the vanilla ones but she went straight to the hardcore ones. After about 30 minutes I "drew" the anal question and while not fully on board to the idea of anal she didn't give a "No" answer. When it was my turn, with my stomach in my throat I said "Yes and Yes." Hazel looked at me with a questioning expression and I said "We both have buttholes. Have you ever heard of Pegging?" We continued on with the game and some interesting things came up which hopefully will lead to new experiences but back to the topic at hand.

My next time at the project I went back to the sex shop and got us each a We-vibe vibrating plug as Wedding Anniversary presents. By the way the reviews for the phone controls are accurate, they are not good. Decent product but synching is a pain. When I pulled them out to use, I could see that Hazel wasn't as ready as I was, and understandably so, so I decided that mine would be used first. But to help with my uneasiness, she would need to put it in me.

I had just showered and prepped my anus with lube and had her slide it in me. My cock was stiff, not rock hard, but solid. We played with the controls some and by the time we were ready I was rock hard and she was soaking wet. As I slowly inserted my cock into her, she started laughing. While I could feel my entire loins vibrating, it hadn't dawned on either of us that these vibrations would continue to the tip of my dick. She tried to apologize but I was laughing as well. If laughing with each other at this intimate of a moment isn't a sign of love and comfort with each other I don't know what is.

After we regained our composure and got down to business the actual act didn't last long because I came quickly. Due to our positions the plug fell out mid orgasm. While not a total success we were together and weren't freaked out. Before anyone says," But she didn't cum", I'm a considerate lover and always makes sure that she orgasms at least once before I do.

After we were done, I asked why she didn't want to try hers, was she not comfortable, not interested, or any of a multitude of reasons that were perfectly fine. I was just curious to see if I should ever bring it up again or just dispose of the toy. I mean her ass her business. Considering how much she enjoyed a finger inside her while in doggy I didn't think that it was due to a fear, I was just curious. She told me that she was really interested in it but didn't want to hold back if the orgasm was as powerful as she had hoped. Hazel can be quite vocal and with other people in our house, probably not a bad idea.

Fast forward a couple of home trips and she couldn't wait any longer and wanted to give the plug a try before moving up to the vibe. Ever the one to let me take the lead, she bent over on the bed and presented her ass to me to explore. Never one to pass up the chance, I loosened it up with my tongue while I played with her clit and pussy with my hands. When she seemed good and ready, I used the lube and slowly inserted the purple plug. I'm not sure if I find my wife's ass sexier wearing one of her lingerie g-strings or walking around with the flat end of the purple butt plug. After some more foreplay with me eating her out, she was ready for her orgasm with the vibe.

I got the vibe ready and as soon as I slowly removed the plug, the vibe replaced it. We got my phone to sync with it and played with the vibrations some and got into a pattern that she seemed to enjoy. And when she responded with "You better hurry up and fuck my pussy hard" my assumptions were proved correct and obliged I did.

This wasn't a soft fuck this was one with passion. With desire. It didn't take too long for one of her powerful orgasms to rock her. I've found that she has like four main types. A soft one where she stares into my eyes and we have like a full body contact orgasm. A medium one where she wants me to pound away and moans. A spiritual one where she cries afterwards. She has had a few of these in the time that we have been together and freaked the shit out of me the first time it happened. This was a day or so before she told me that she loved me. Next time when we were about to move in together, then after we were engaged.... Major life moments.

Then we have the ones where the earth seems to move under her feet, or ass actually. Just as she is peaking, her left hand goes up by her head on her left side and starts hitting the pillow her head is on. Imagine a bull rider on a bull and his hand is in the air for the ride. While all of this is happening, it seems like she stops breathing and her eyes are closed tightly like she is trying to prevent them from popping out. I can't recall this happening in any position besides missionary. There have been times that she has drooled on the bed while in doggy so perhaps the reaction is different in that position.

Anyhow, she let loose with one of her powerful ones and seemed to fully enjoy the plug until it slipped out mid orgasm. After we were both done, I hurriedly grabbed the plug to not freak her out if there was any material on the plug and placed it on the ground. We then laid in bed with her unable to control her legs while we just held each other and basked in the glow of our mutual exploration of ass play.

A few months later I was about to leave on another project and decided that it was time for her to stretch me out and I began my investigation for a strap-on. While I would have loved to bring her out shopping, the trouble of getting both of us out of the house at night made it impossible. Plus, I wanted to surprise her with it. I wanted one that would fit her correctly, comfortably, and provide pleasure to her. While the underwear ones seemed to get the best reviews, I was afraid of trying to size her....milfly ass and decided to get one with adjustable straps. Plus, I wanted one that had a good built-in vibrator so we could both enjoy it. I settled on "Her Royal Harness". The straps were adjustable, padded, and sinched down tightly. The base of the dong was touching her clit and not a thick pad on the harness.

The day that I bought it, the time until we could go to bed seemed to drag on forever. As she was closing up for the night, I placed the assembled harness on her vanity. The gasp then laugh that she let out when she saw it was worth the wait. As she walked out of the bathroom holding the dong with a questioning look. I showed her how it was supposed to vibrate against her lady parts and was fully adjustable. It was too late to play with it, which was perfectly fine, but we had crossed the threshold and both of us were willing participants.

After this step was complete, I needed to figure out the position. Some of the things that I read recommended doggy as a first time which seems like it takes away the personal connection and I guess that if this is your partner's idea, it may not be a bad way but it was my idea. I wanted to see her face and wanted her to see mine. I decided that maybe we do it in the bathroom so we can do it standing doggy and can see each other in the mirror. Step Two, check.

The night before I was getting ready to leave, we were laying in bed and I played a comedy pegging video where the woman was more into it that the guy. Step Three, check.

We started just normal foreplay and after eating her to an orgasm we got into position and we started typical PIV action. I kept getting close to orgasm but kept stopping and Hazel asked why I stopped since she was well onto her way every time. After the fourth or fifth time I said "You are going to fuck me tonight" and grabbed the toy from our chest. For the few minutes it took to get it, adjust the harness, and turn it on, my cock didn't soften in the least. I then grabbed the prostate plug since it was slightly smaller than the dong to stretch out my anus some and prepped myself. I gave Hazel control and she slowly inserted it and either my ass didn't want to give up control because of her lack of confidence or my prep work wasn't sufficient because it hurt more than it had in the past and I had to postpone the event and removed the plug.

Not to be deterred, I got up and stood in front of Hazel. Presented my ass and looked at her in the mirror. Her confidence was building but she couldn't get either the angle or height right and couldn't take me. We walked out of the bathroom and her confidence continued to grow and she told me to get on all four. While for here on out, if she tells me to get on all fours, I will willing do it, but I needed to take the receiver position their back and give her the dominate top position.

As I got onto the bed and positioned onto my back, being my first time, my butt rolled away from the edge. We laughed since she has had to reposition herself before. With my legs in the air and her cock pressing against my anus, a power shift happened in an instant. She became dominant and I opened up immediately. There was no cramping of any sorts and she was able to thrust. Step Four, Victory lane crossed.

She started stroking my cock but soon just grabbed my hips and started pounding away. The look in her eyes was nothing that I had never seen. This look was causing my cock to somehow only get harder. I needed release and started stroking myself. It didn't take too long and my orgasm was in my top five for most powerful. I had thought that I would have shot it over my head but it all had landed on my stomach and chest.

I had to jump in the shower to rinse off and cleaned the toys and put them away since I was leaving early the following morning.

The morning after she took my last cherry I couldn't figure something out. I knew that she had an orgasm prior to fucking me but her comment of "You aren't done yet go and get toy because I need another one." kept echoing in my head. I called her up and asked for clarification. I asked "Didn't you orgasm prior to putting on the harness?"

"Yeah, I had a little one but I was too amped after the event to go to bed. I need another orgasm to calm down."

I laughed and said "Good, I was afraid you hadn't before."

"Oh no, I did, but it was just so thrilling to do that. When you first brought up the idea, I wasn't sure what was going on or how it would go but we are in it together. Then when we started, I got more and more into it."

"I had hoped that the vibrating dildo would help you to enjoy it."

"The vibrations weren't in the right place but the power from my position in it got me on edge and it would have taken half the night to come down from the high without another release."

"If you enjoyed it then we can look at getting a strapless strap-on that goes inside you."

"I know those things."

"You do? Freak. Well thanks for clearing up my question. Love ya."

"I Love you too". Step Five, Victory Lap was good.

While the first time wasn't as physically pleasuring as I might have hoped, the mental side was better than I ever could have imagined. When we try it doggy, I'll make sure we do it in front of the dressing mirror we have. Plus maybe film it, I have to see that look in her eyes.