First Time Pegging [FM]

So me and my GF recently moved countries and as such had to put our toys into storage.

We’ve been settled in and had some spare cash so it was time to buy back some of our gear… We ordered a pretty basic assorted kit (rope, nipple clamps, hog tie, blindfold, gag etc) some restraint belts, a set of metal plugs (with pink gem’s on the base) and something we’ve never tried before….. A strapless strap-on. We’ve done some anal play before but she wanted to try pegging, she decided she wanted a strapless one because it’s unfair if she doesn’t get some pleasure too!

The weekend came and around mid-day she told me she was going to get a shower (pretty unusual as we usually shower before we go to bed) but I thought no mind to it and continued watching TV. After her shower she was spending a long time in the bedroom but again I didn’t pay much attention to it. She then emerged from the bedroom and I knew I was in for a fun afternoon. She was wearing stockings and garter, a black wet-look and lace dress (with a zip down the front for easy access) and her black lace dressing gown and god damn did she look fantastic! She sat on top of me, paused my movie and informed me I was to get a shower and clean myself thoroughly. I was immediately rock solid and couldn’t wait for what she had in store for me. I got a shower and cleaned myself (and my ass) and fortunately I shaved myself the other day so I could get it done pretty quickly. After I got myself dry, and resisted touching myself, I went to the bedroom where she was waiting with the new toys spread across the bed.

She began by inspecting me, making sure I was clean and appropriately shaved, grabbing my dick and ass and squeezing, making me squirm for her. Next she took out the plugs asking if I’d like to start with the small, medium or large plug, the largest is pretty big so i opted for the middle size before bending over and allowing her to lube me up and insert the plug. Of course she took her time over it to tease me and slipped her free hand down to caress my balls and now extra hard dick. Now she asked me what i’d like to wear, she knows I love lingerie and have a small collection of Men’s Lingerie along with some stockings and garter belts, but I enjoy it when she tells me what to wear it makes me feel much more submissive. I told her I wanted her to choose so she gave me the option of what colour, I answered “not black” knowing she has a variety of underwear that I can fit into (we’re very lucky in that aspect) and she picked out two of her baby-dolls, one red with peepholes for your nipples and the other lilac and pink with a black harness-like design on the breasts. I went for the Lilac baby-doll and she quickly told me to put it on, helping with the clips at the back. Then she took out the rope and tied a rope dress over the top, making sure to tie it around my cock and balls nice and tight (it also felt very good against the plug) and put me in front of the mirror telling me how sexy I looked and again caressing me and pulling the rope to watch me squirm.

Now we were both ready to go she had me repeat our rules:

1. No cumming until Mistress tells me to.

2. No touching myself unless Mistress tells me to.

3. No doing anything to Mistress without permission.

It had been a while and I got a little stuck on the third meaning I got some spanks before she told me the correct answer.

This is when she got very mean. Mistress told me to go back to the sofa and continue watching the movie (I had 10 mins left on it) and proceed to sit next to me and touch me wherever she pleased under the strict instruction that I must stay perfectly still or she will rewind the movie or even start again. After a horrifically long 10 mins of Mistress playing with me and herself (even placing her juices on my cock and putting her fingers in front of my mouth but not allowing me to taste them) the movie was over and I was led back to the bedroom.

This was when I was restrained with cuffs on my wrists and ankles and blindfolded as I lay on the bed. Mistress quickly began to tease me, gently touching me as well as telling me how sexy I looked and slowly explaining what I was to do to please her. I asked if I could touch her and begged to be allowed to please her in whatever way she wanted, I was rewarded for being a good sub by her pressing her pussy into my face and after a few agonising moments being told to lick her pussy until she told me to stop. As you can expect I began quickly pleasing her, she tasted so sweet and she was dripping wet her juices going everywhere and Mistress ground herself into me getting as much pleasure as she could. After a few moments of bliss I was told to stop but she didn’t remove herself from me proceeding to use her mouth to tease me, licking the tip of my cock as well as playing with my balls and scratching my legs to make me squirm. I begged her to let me please her but she only laughed and teased me my cock responding for me with a shudder.

She then moved onto the next part of her plan, removing the rope and commanding me to lay on the bed (on my front) she hogtied me giving her access to my plugged ass. She removed the plug, with a bit more teasing and slowly began to tease me with the large plug. She gently teased my willing hole all the while praising me, telling me what a good Sub I was and how sexy I looked wearing her lingerie, but the large plug was just too big for me to take without some minor pain so she moved onto the new strapless… she made sure it was well lubed and began pressing it against my hole. My ass greedily accepted it and she made sure to take it slow and make sure I could take it before she could properly fuck me with it.

After an excruciatingly long time I began begging her to fuck me with it, I had been waiting for it and knew she had too. She took off the hog tie but left my cuffs on and commanded me to lay on my back, she positioned herself with her cock pressing into my hole and I raised my legs and hips to accommodate her better. She then removed my blindfold and slowly began to fuck me. It was a little uncomfortable at first and getting into a rhythm was a little awkward but eventually we got into a rhythm and she took my cock in her hand jerking me as she fucked me. It wasn’t long before Mistress wanted to try a different position, putting me on my front (head down ass up) and continued fucking me it was still pretty gentle as we didn’t want to push it on our first try and we tried doggy and reverse cowgirl too (is it still cowgirl if it’s a boy on top?). At one point I even jerked of Mistress’ cock since it pushed it deeper into her and rubbed against her clit (first cock that wasn’t mine I’ve ever done that too!).

But i’d been close to cumming for a while and mistress knew it. While I was on top she told me I was allowed to cum and she wanted me to jerk myself off with her cock deep inside me…. I didn’t need to be told twice and had an amazing orgasm. I could barely move, barely breath and fell into her arms.

*Hope you enjoyed our first foray into pegging and my first try at writing something like this!*

*TLDR: I got pegged.. It was great!*

Source: reddit.com/r/gonewildstories/comments/c84c84/first_time_pegging_fm