I love reading the stories in the forum so thought I would share one of my own about my first time being pegged, which also ended up being my first time being caught..... hopefully it reads ok.
I had been seeing a dominant married older lady and we had met quite a few times. I was 26 and she was 43. We had tried a bit of gentle bdsm. Bondage and edging mainly. Some spanking, watersports, butt plugs. We had been pushing some boundaries and we decided we would like to try pegging and cuckolding.
So for our next meet We were staying in a lovely hotel and When we arrived we noticed that the hot water was not working in the bath, so we called down and were told someone would be sent to look at it, but due to being very busy it might be an hour or 2. In the mean time she ordered that I dress up in her underwear and stockings and massage her and worship her feet, pussy and arse. Whilst enjoying this task so much the time flew by, and we thought they must of forgot to come and check the water.
Mistress then tied me down and started to tease and edge my cock. Making me throb and leak precum. Begging her for more, she stopped playing with my rock hard dick. Stepped back and looked at me tied to the bed wearing her underwear, with a menacing look on her face she asked "how badly do you want more, how badly do you want to release?" So I begged, please Mistress, let me cum for you, I'll do anything.
This statement was the start of the events that were to occur. "Anything?" Was her reply. "Yes Mistress, I will do anything for you to let cum"
With that she walks away and returns with something in her hands. I soon realise it is a blindfold, she leads forward, kisses me on my lips and blindfolds me.
The next thing I hear the zip of her weekend bag opening up. And the clicking of buckles being tightened. Then I feel Mistress untying my wrists and ankles. She tells me to get on my knees and bend over to which I happily do. Mistress climbs onto the bed behind me and starts to rub her strap on up and down my arse, teasing me with the tip.
She says to me, "would you take my strapon in your arse if I let you cum anywhere you like?"
My answer was a swift yes. With no thought or hesitation at all. Mistress removes my blindfold and instructs me to watch in-between my legs while she penetrates me.
Mistress started to massage my arse, gently spreading my cheeks whilst pushing her strap on slightly deeper with each thrust. As I start to relax into the thrusts, gently pushing back against her whilst she slaps and strokes my arse cheeks. Mistress starts to start going harder and deeper.
I am really enjoying the feelings of Mistress taking me like I am her slut. I can feel the balls of her strapon slapping against my balls which only adds to my feeling of being her pathetic sissy slut to use how she likes.....as I am lost in this thought, feeling my cum building in my balls ready to explode......I hear the hotel room door open.
There is no time to stop what we are doing or hide from whoever is walking through the door and as we both look up, holding our breathe in suspense, mistress holds her strap on all the way balls deep inside me as a late 30 something maintenance guy walks in and looks up to see me bent over on the bed, wearing red stockings, red suspenders, red crotchless knickers, with Mistress clearly mid way through fucking my sissy arse.
Instead of walking out or looking disgusted or embarrassed He looks up with a kinky look in his eye and says "don't let me stop you". And shuts the door behind him. On hearing this mistress takes a handful of my hair, pulls her strapon all the way out and thrusts all the way back in, making me take every inch.
With my face in the mattress getting fucked hard by mistress and being lost in the moment, I forget we are being watched by our mystery guest, until I hear her say "why don't you bring that big Dick over here and join us on the bed", as I glance across the room I see maintenance man getting up from the armchair completely naked with his Rock hard 8 inch cock in his hand. As he walks across the room he is stroking his cock, pulling back his foreskin to reveal his big throbbing helmet.
He sits on the bed in front of me still stroking his big hard cock right in front of my face. The whole time mistress is still fucking me hard and deep. She has reached down between my legs and is squeezing my balls. I hear her saying "how desperate are you to cum my filthy little slut" and my response is again fast with no hesitation "so desperate Mistress, I want it so bad, please let me cum Mistress"
"Suck his cock and I'll let you cum anywhere you like" Mistress knew I had some bi experience and that cuckolding with bi bulls was something I wanted to try.
So in my extremely horny state and desperate need to feel my sissy cock release my cum, I reached forward and start to kiss and lick around the tip of maintenance guys huge hard dick while he Strokes it with a firm grip. Mistress slaps my arse hard and says "I told you to suck his cock slut" and as I open my mouth to oblige I feel her hands pushing my head down onto him, getting his dick deep in my throat and holds me there for what felt like forever.... as I started to gag she let go and my head came up for air, maintenance guy told me to spit on his cock and as he did he moaned out loud and pulled my head back down onto his hard cock again until I gagged, then letting me up to spit on his soaking wet cock again. His cock pulsed multiple times and he said I need to explode, he got to his knees and in perfect rhythm with Mistress pegging me he started to fuck my throat holding my head in place.
With Mistress picking up pace and maintenance guy fucking my face harder and deeper, saliva dripping down my chin, splashing up over my face with every deep thrust into my throat. I could feel his cock swelling and tensing up, with his growns getting louder and deeper. He pulled his throbbing shaft from my throat, stroked his dick a few times and let out a deep long moan as he shot stream and stream of hot cum over my face....
He stood up and said to Mistress thank you for letting him stay and enjoying her sissy. He would be finished work in 2 hours and would we mind if he came back to join us for some more fun. Mistress said it would be a pleasure to have him come join us again and that she wouldn't let me cum until he returned.....
With that he slapped my face 3 times and said, "don't worry you little sissy, I won't be long, and then you can be treated like the proper little sissy cuckold that you are....". He put his trousers on, straughtened himself up, and left with a kinky grin......
|
. Please continue 
