Hey together,

just wanted to share my second time with my favorite professional, regarding pegging.

Two years ago, in 2022, I spontaneously found on holidays a professional of 24 years, who had a very passionate profile about offering pegging. Already her pictures wearing the different dresses and below the hughe strapon made me hard (Police officer, nurse, cheerleader, prisoner, tight leggings, leather skirt) and I really wanted to visit her. She mentioned as well, that she is no mistress and is doing this for passion. Fortunately she is still working in this business. Consequently I contacted her again this year on my holidays. Due to the fact that I am single at the moment, it wasn't a big deal, it was all about the money.

Fun fact was: She told me the location (district), where she is located. It was quite clear in which area it will be and I chose an AirBNB "close" to her and now comes the fun fact: She was working in the building, where I rent my AirBNB as well. I had to laugh about it quite hard. Now it was just about finding a proper appointment and we chose the early evening for a two hour pegging session. Addionally I asked her, to organize some weed, because pegging on weed is for me so intensive and I can orgasm without hands being on weed as well. She said, that she has something in her place and will be ready on time. Furthermore she sent the picturs to me of her dresses, that she can use for our appointment. I chose the leather mini skirt with a black leather top, it looked great on the pictures and I like that glossy leather look.

The afternoon of the appointment, I started to prepare properly for pegging. I made a deep enema, shaved my butt, shaved all the other parts of my body, dressed up in jogging pants but used perfume as well, to feel nice and smell good for her as well. The time of the appointment arrived, I got ready and took some of my toys and special things with me: My prefered dildo, towels, silicone lubrication (i am circumcised and prefer way more handjobs with silicone lubrication, instead of water based one), an anal plug and XLube in a big litre bottle. The XLube is absoloutely my favorite, because it doesn't contain glycerine, like most of the normal lubricants. From those I get horrible cramps and buring sensations in my colon and I have to press it out immediately, due to the horrible pain. With XLube no issues at all.

After I got all together, I went in the elevator, drove up in the 6th floor and went to her communicated room number. Her door was already slightly open, I knocked and she opened the door in her beautiful dress. She looked amazing in it and got a big smile on her face, when she recognized me again (I changed my mobile number from the last to this time). We hugged each other, went to the bedroom and talked how life was going. During our conversation, we started to share a beer and I prepared a joint, to smoke some weed before the session.

The weed kicked in quite fast and hard and we talked about the expectations for this evening. I told her, that I wanted to get a relaxed massage at first. During the massage she could start to massage my anus and put the anal plug inside of me, to stretch everyting a bit more up. After this preparation I wanted her to pegg me in doggy position and then in missionary position.

She asked, if I also wanted PIV intercourse - and I said: Yes, after I came by pegging, it would be great to do so. She smiled and said: Okay, let's start, get naked and lay down on bed.

I removed my clothes, she played some nice music and I layed down on her bed on my belly. Slowly she started massaging my back and shoulders and slowly working down to my ass. She massaged my booty at first and slowly worked forward to my anus, that she lubed up and started to put inside slowly first one finger and then another finger. And commented immediately: OMG, you have a big asshole, you are used to it. I replied, that she is right and she mentioned already, that later she wants to find out, how many fingers she can get in my ass. But at first she was putting in the anal plug, to widen up further. After about 20 minutes, she removed the anal plug and started to give me black kisses, what I didn't expect. She licked my asshole and really enjoyed it. Mentioned several times, that my ass is very clean and open up wide and that she loves it. Several minutes she suddenly applied cream on my anus and I asked her, what it is for. It was cream with Lidocaine, a local anaesthetic, to make it less painful on the hemorrhoids. I trusted her and we left it there about 15 minutes, to work properly.

I smoked some more weed during that time and she prepared herself with the leather harness. She put it on her skinny hips, tightened up the straps and mounted the first dildo, to fuck my ass with. She asked me, to come back to bed in doggy position. Obviously I didn't say no, went into this position, relaxed and she filled me up with some of my XLube and applied a big amount on her dildo as well. Slowly she came close with the dildo to my anus and finally, slowly, pushed it inside. It was such a joy. She started moving her hips in rythmic movements, it just felt outstanding. She also enjoyed and offered anal sex as well, without size limitations. Due to that fact, she knew exactly what she was doing, what were the limits and how to make it most comfortable for both.

After about ten minutes I asked for a bigger dildo. She changed the dildo for the next one and started to fuck my ass again with this one, after applying more lubrication to my anus and the dildo. Amazing!

Suddenly she pulled the dildo out and asked me, if I want her to stretch my ass and try to fist me. I agreed. I also brought some single used medical gloves. I love those ones, have a fetish for this material as well. She put them on, like in an examination and lubed up her fingers. I was still in doggy position and she entered with two fingers at first. She moved the fingers slowy in and out and proceeded with more and more fingers. Finally she asked me to guess, how many fingers she now had in my asshole. I told her: Three. She said: No no no, I already have four fingers in your ass until her knuckles. It felt amazing, to be so stretched. She tried further with her thumb, but it didn't work this time, so we stopped and proceeded with my favorite dildo.

She took it and was amazed of the structure. It was the blush novelties dual density dildo, 18cm long and 1,75" in diameter. Lubed up again, she inserted the dildo into my asshole and fucked me passionate with my favorite dildo.

I asked her to change to missionary position, because I love the intimate feeling, of being down, having my ass fucked, being hugged by your pegging partner and feel body on body. She agreed and we changed positions. Now I could see her pretty face on fucking me. She dropped into me and moved passionately again her hips. It was so hot and we had such interesting conversations about my fetishes and pegging as well. It was just outstanding an so enjoyable to me.

Her hips were just moving perfectly, to give me deep thrusts into my asshole and hitting my prostate properly. My climax increased and increased and increased. She looked in my eyes, was moaning, told me my fetish favorite things and I couldn't hold my load anymore and just orgasmed between our bodies. It was flowing out of my dick like a river!

We stayed in this position for several minutes, just hugging and touching each other, it was such an intimate feeling. After she removed the dildo, we cleaned up shortly, just layed in bed, cuddled and hugged each other. Drank another beer and talked about our normal lifes. I left also my dildo with her, as present, because she really loved this one so much and was also amazed about the XLube.

I was such an intense experience again. I enjoy every thrust of her and with the lidocaine and tons of lubrication on the anus, it just made everything feel a bit smoother. After those pegging sessions I am always very girlish, want to cuddle, be loved, I am very sensitive and just want to be taken care of. I love it, to be so breakable from time to time.

Two days later, we met again for another pegging session. Maybe I will make another one from this.