Hey Guys… This is Arjun, from new Delhi working as an Engineer in USA. Im single guy living far away from home and trying to explore the pleasures available. Im well built and fair who also has good interest in sports.
My routine is very simple….I work and hit Gym and cook healthy foods then talk to my parents and go to sleep. I have few friends around and socialize with them during weekends. So, Now let’s begin my story about I lost my ass virginity to dominant mistresses in Vegas and how I found my best pleasure in life. I watch porn sometimes and one day I saw a video where a woman sits on a man’s face and torture him without giving a break to breathe. This video made me so hard and I came like never before. This is when I started watching more FEMDOM videos and pleasing myself and one thing led to another and started watching STRAP-ON pegging videos.
This made my mind blown up and I had the best orgasms I ever had. From then I stopped watching regular porn and was only watching pegging porn and was really enjoying it. So, one day I thought I would like to give it a try and bought a butt plug and lube and started enjoying it. That session gave me a good orgasm and I went on with small dildos and mastrubating with one hand and inserting with another hand. For a few days this went on and I was having the best time.
Then slowly I decided to try this on with a real woman who can properly fuck me in my ass and give me a nice pleasure. I have a fuck buddy and she and I will have sex sometimes whenever she needed. She has a kind of dominating personality and have a great body and always rides me (cow boy) and very less times she allows me to fuck her in missionary. She always controls my orgasm and forces me to stop myself until she cum. She only comes whenever she wants and never comes for quick booty calls if I ask. We maintained this relationship for 1 year and along the side I was enjoying my pegging fetish.
So, One day during our session I started playing STRAP-ON porn and started to give her some idea about this dominating sex. I was expecting that she would get angry for showing some BDSM sex but instead she started watching with more interest and wasn’t even looking at me. She pleased herself and didn’t even touch my body and came so much. As she enjoyed watching that porn then I got some nerve to ask her how about we try this on me? She was a little surprised and told me It’s not possible and it would hurt me so much. She kind of tried anal sex before with some one but it was a disaster.
She was trying to explain to me that she can do some face-sitting and spanking stuff but pegging is too much and doesn’t want to hurt me. I understand her fear but was really horny and wanted to try this with her as she was my only hope. So, i bought few of my toys from inside and showed how much serious I’m into it and asked her to try out butt plug on me at least. She accepted it and used some lube and inserted that small butt plug inside me. As I had some practice already it went smoothly and she started pulling and putting it back. She kind of started enjoying it and was doing it with little pace and also giving me blow-job (she usually doesn’t – But allows me to give her a mouth job). I came so much to her face and she also enjoyed it so much and was very impressed to see me cum so much. Later she forced me to give mouth job by sitting on my face while watching some FEMDOM porn.
She made me lick her ass as well and was riding on my face. Within a few minutes she came so much and I felt some bubbles bursted out of her pussy and some sticky liquid inside my mouth. It was the best night I ever had with her and she agreed to do a STRAP-ON sex with me that weekend. So, we went to an adult store and bought some harness and medium sized dildos, had some wine and started watching porn. We both were a little high and started getting horny and decided to start pegging. So, without any delay, she ripped my clothes and under pants and pulled me to the edge of the bed and bent me over. I was very excited and scared as well. I already shaved pubic hair and cleaned my ass using an ENMA bulb and hot water to avoid unnecessary mess. She put some lube on her fingers and on my ass and started inserting them while she pleases herself. After little preparation I helped wearing the harness and dildo attached to it. She asked me to give blowjob on that dildo. I was a little hesitant at first but don’t want to disappoint her. So I gave a nice job to that dildo and she bent me over again on the edge of the bed. she applied some lube on the dildo and some on my ass hole and started inserting it.
She thought it will go very smoothly as how a dick goes inside a pussy. With out any warning she gave strong stroke. I was in lot of pain. She said sorry and helped me relax the muscles around my ass. We waited for 15 min to calm down my pain and I was very sad that it went wrong the first time. I was scared to take that pain again but do not want to miss the chance of getting pegged. If this doesn’t work out tonight it kinds of break our deal as she already warned me about the pain. After some time I asked her again to try out this time but gently. Even tough she did it slowly it was giving me so much pain which I couldn’t take it. I think that dildo was not for beginners (website suggested it wrong). We tried some other small dildo but nothing worked and we stopped doing that and she left saying we are not doing this again. We only met few times after that for our regular sex and later she moved to a different city. So, the thought of getting pegged was still my dream. I did not stopped using butt plug and watching FEMDOM porn and pleasuring myself.
I got so frustrated as this was running back of my brain everyday. So, one day I decided to try this out one more time to see if this will ever happen, if not will stop thinking about it. My fuck buddy did not accept my request but suggested to hire someone for this. One of my friends gave me a stripper contact long back and I thought will give it a try and what harm it could cause. So, I called her and told her that I got your contact from some one and directly asked her if she can provide some sort of service. She said yes and quote very high price. She gave her Instagram id to check her profile and can decide on it. She was very hot and a professional dancer and looking at her couldn’t control my thoughts and called her again. I told her that Im not looking for regular sex but instead asked her to fuck me in my ass. With out any thought she said ok and this shocked me a little. I was very happy that she accepted and asked her one more time if she is really ok.
Then she told me she is bisexual and always have fun with boys and girls. She had good experience using STRAP-ONS on girls and guys. I was so excited listening to this and told her about my past experience and that painful scenario. She assured me that she would take it very slow and has a good experience pegging virgin boys. She had few bi guy friends and tried this STRAP-ON on them. I was so happy and excited as finally my dream come true. She works in Vegas so I booked my flight and a nice hotel room and booked a 2 hour appointment with her. It was some weekday and she was not working that night. She asked me if she would bring a friend and I was like more the better and said yes. Both girls came to hotel room and I paid some money first and started talking. Then they asked me to order some liquor to enhance the mood talking nicely and sitting on my lap. We all three had few drinks and then we started to have fun. Her friend was sitting on a chair watching us and the main girl asked me to kneel down and forced me to sniff around her pussy and ass. It smelled so good and instantly turned me on was having hard rock dick. I started playing with my dick but she put her leg on it and said “It was only me who is going to touch that tonight.”
OMG!! it was so good listening to that later she asked me to suck her boobs. After enjoying those nice aromatic boobs she asked me to do strip dancing for her while she and her friend watching me taking one cloth at a time. Once I was naked told me do the hip movement so that my dick would dance. Both started laughing looking at my dick and trying to humiliate me. To be honest I have good medium sized dick (5 inches) but they said they saw 9-10 inch dicks. She hold my balls and dick with one hand and was scolding me very harshly by saying you have this pathetic dick and you thought you can get this pussy for this. She forced me to walk on fours like a dog and asked me to bark looking at their beautiful bodies. I was dragged around the room and she was spanking my ass while doing it and also kicking with her heel on my ass. Her friend was enjoying this show so much and giving her some instructions to humiliate me.
Later they tied me to the bed using handcuffs and my hands were at the back. She tied my legs using ropes to the bed so that i cannot move my legs. I was lying down in doggy position with my head down on a pillow. My ass was up in the air and cheeks were stretched nicely and I can feel the AC breeze going though my asshole. She inserted a butt plug inside my ass and came in front of me. She lift my head and lift her legs so high where I can see her asshole and left my head on that. I was only allowed to lick her ass and if I do a nice ass worship she said she will reward me. If I go to lick pussy she said she will punish me very hardly. I tried a lot just to stick my tongue to her ass but her pussy smells so good and that juices coming from her pussy were so tasty. I couldn’t control myself and lift my head to taste that pussy for a bit. She held my head and slapped me on my face and asked me why did you lick my pussy? I said I’m sorry but she did not accepted my apology and decided to punish me. As she was also enjoying my ass licking, she didn’t want to get up and asked her friend to spank me hard. I got some 10 hard spankings on my ass cheeks and 10 whips. She said as it was my first time she is not punishing me hard. After some ass worship she said she going to fuck me with a realistic dildo she bought as this could be easy for the beginners. It was a 6inch dildo with nice craved nerves and was in jelly material. I was in the same position and her friend helped her putting that STRAP-ON. She also wore some black gloves and was looking like a great goddess with nice tattoos on her thighs and fishnet leggings. First she took lots of lube and on my ass and made it go inside using her fingers and butt plug. It has become so smooth now that I can feel her fingers going in and out easily. Now, she warned me that it might pain a little but you need to hold that dildo inside you to make it work. She slipped lots of lube on her dildo and started with the tip and inserted it slowly.
She asked me to relax and take deep breathes, and try to contract and release ass muscles. After few minutes she was successfully able to insert the tip inside my ass and it felt so great. It was a little painful but I was able to control it and lost that pain after few seconds. She appreciated me for doing a job holding that dildo and gave me another small push. It was so amazing and I started feeling so great as something is inside my ass and my dream coming through. After few minutes she completely inserted whole dildo inside my ass and I can feel a big gap filled inside my anal and it started giving me a great pleasure. She slowly pulled it back and pushed it again. This was good and I was really getting fucked inside my ass. She started doing it more frequently and also applied nice lube in between strokes. After sometime her friend said that his ass his ready now and pound him hard baby so that he will never forget you.
She grabbed my ass with her hands and stroking that dildo inside my ass fast like the same way how a girl gets fucked. I was screaming in pleasure but still dick was not so hard as it is not getting enough attention. I asked her to shag me but she refused. Her friend said its ok give him some sugar but it was little hard for her to give me a hand job while pounding my ass. Her friend cared to help and she held my dick and started stroking it while the main girl fucking me. Ohhhh!!! It was sooooo Goooood!!!. I can never forget that experience. After few strokes It was rock hard and was ready to cum. I told her that Im ready to cum. Her friend removed her hand listening to this and said I don’t want this slut cum on my hand. Girl who is pounding me stopped and held my hair and pulled me back. She said if you cum I will punish you so hard that you will never forget this pain and said you still have 1 more hour and session will be done if you cum. I don’t want to get punished and want to receive more pleasure and receive whats my money worth. So, i controlled myself and said I was ok. As i did a good job controlling my cum, she kept a nice pillow under my dick and make sure my dick gets rubbed to those soft silk pillow cover while she pounds me. It felt so good as I was receiving pleasure from both back and my dick in the front. After sometime we decided to switch positions and asked me which one I prefer, a missionary or cow boy? Before I even answer Her friend suggest to ride the dildo as it would look great.
So, my bondage was removed and my legs was shivering from whole 10 min pounding non stop and sat on the bed. After few minutes, that girl slept on the bed and asked me get on her and put that dildo inside my ass. I happily climbed on her and applied some lube over my ass and dildo and trying it insert it. I tried lot different styles to get that dildo inside me and she was also trying to help me but it was not successful as we both were not able to see the tip or my ass hole. Her friend cared to help but demanded some extra bucks. As I was so horny I agreed to pay and let her help me getting that dildo inside my ass. Finally it went inside me and filled my whole gap in the ass. Her friend helped me stay intact with the dildo and helping lifting my ass over that. After few minutes i got the nice grip and was squeezing my girls boobs while riding down her STRAP-ON. I was going up and down and up and down and feeling great sensations inside my ass. as I was squeezing her boobs she was also enjoying that please and looking at her expressions made me so horny. In between her friend cared to stroke my dick while I was riding the dildo and she would leave me if I said I was about to cum.
After 10 minutes of riding I couldn’t resist my self and was going so fast up and down riding that dildo and was creating a great pleasure inside my ass and triggered my prostate gland. As her friend is stroking my dick while looking at her phone this time I did not warn her that I was about to cum. Even my mistress closed her eyes as I was playing her boobs. I was about to say that Im going to cum but before that words did not came into my mouth and suddenly I exploded. It was the greatest pleasure i ever had in my life. Felt like my whole body got orgasm and. all my parts were shivering with pleasure. I came so much that it went all over my mistress body, her face, eyes and even on her hair. It was so much cum I ever seen and I came for about 30-45 seconds. Ohhhh god it was best thing ever happened to me in my whole life. I also came on her friends hand which made her angry and kept that hand inside me mouth to clean it. I did not hesitate but cleaned that cum from her hand. My mistress was happy that I enjoyed too much but was furious about all the mess. As she did not give permission to cum, she said as a punishment you need to clean your cum from my body. I was little hesitant at first and thought well I already tasted some and whats wrong in cleaning it all? I cleaned her whole body and this way I got to lick her whole body which was covered with all kinds of mess like her perfume, her body lotion, some make up, sweat, and my cum. It felt little weird but I though I should clean her as she gave me the greatest pleasure of my life.
There was some 30 min left in the session but she asked me do you want to try anything else before we leave. I wasn’t sure as Im already exhausted said I’m good. But her friend suggested why don’t we give hime some golden shower and make hime feel filthy and disgusting. I wasn’t sure about it but they both dragged me inside the bathroom and made me sleep in the bath tub. My mistress shagged herself and started squirting and released her golden shower on my face. I closed my mouth all the time as I felt so disgusting. Later her friend though I did not receive the good shower and she removed her skirt and panty and came into the tub and squatted herself near to my face and hold it.She showered all over my face and head. Then they left me like that for some time and asked me to go out.
They both took nice shower helping each other and it was so sexy to watch 2 girls scrubbing each other in a tub. Once they got freshen up they came out and asked me to pay more. I asked why I already paid the agreed amount along with the tip to her friend. They said it was charge for regular sex. For all these fetishes they charge double and some charge for their toys. Her friend also demanded more money as she shagged me and I came on her and also wanted to charge extra for golden shower which I did not asked for. I felt like I was cheated but have no other option to pay them.. thats how I had my first crazy pegging experience.
I hope you like this story and let me know your comments and reviews to [email protected]. My next story would be around how I got my fuck buddy to get trained as a strap-on mistress from one of my neighbor and how I was Involved in an awesome foursome swinging pegging.
