First post on here, hope you enjoy.
Just a little bit about us, Jenn is 5 ft 5 with light brown hair, 36DD tits and a round ass that fills out jeans perfectly. I am 6 ft 3 with a shaved head, beard, average build, average cock. This story happened last Saturday night.
Jenn texted me and told me she was very horny and wanted to come over. So I went to pick her up. Earlier in the week we had been discussing her needing to have a discreet but powerful vibrator to take on vacations and have in the car, just in case she needed some relief on her commute. I remembered that I bought her a smaller vibrating butt plug and we had never used it. I wanted her to try it out as a vibrator, so I brought it with me to pick her up. Once she got in my car I handed her the plug and asked if she thought this would work. She immediately began rubbing it on your pussy over her leggings, she was enjoying herself. I used the opportunity to lift up her shirt and bra, exposing her tits. I was playing with her left nipple and she was loving it. She was rubbing the vibrating plug on her clit and was soaking her panties. We finally arrived at my house.
We immediately jumped out of the car in my garage and rushed in the house. As soon as the door shut I pulled her leggings and thong down. She then climbed on the washing machine, removed her shirt (her bra was off in the car) and spread her legs. I knelt down and began using my tongue on her clit while she played with her nipples. After she had an orgasm I stood up and slid my cock into her. We fucked furiously for a couple minutes before deciding to take the action to the bedroom. Jenn ran out of the laundry room completely naked, I followed.
Once in the bedroom I removed the rest of my clothes as Jenn climbed onto the bed. She laid on her back with legs spread, I knelt next to her head to give her access to my cock. She turned her head to the side and slid her lips down my cock. I had the plug in my hand and was rubbing it on her cunt. At the angle I was rubbing it, the tip of the vibrating plug would slightly touch her asshole before I pulled it back the other way. She had her second orgasm of the night from the plug being used on her wet pussy. I then asked if she would like me to slide the plug in her ass. (I had used my finger and tongue on her ass before, but never a toy)
Her reply, to my surprise, was yes. I got off the bed and pulled her over to the side of the bed. Her ass near the edge. I used some lube on my finger and slid it in her asshole first to make sure she was comfortable with it, because the plug was definitely larger than my finger. She said that felt good and she wanted the plug. I took my finger out and used more lube on the plug, I slowly slid it into her ass until it was at the hilt, I then turned on the vibration, she was loving it. I then slid my cock in her pussy, she loved the feeling of both her holes being filled. We fucked like that for a few minutes until we both had incredible orgasms. I slid my cock out and turned off the plug, but left it in her ass. I went to go throw away the condom and wash the lube off of my hands.
Once I was back, we laid in bed and caressed each others bodies, kissing and touching. I could tell that she was still horny and wanted more, I needed some recovery time, but could work on pleasuring her while my cock recovered. She asked if I could turn the plug back on. Absolutely, was my reply. I told her that we should go through the many vibration settings to see which one she liked the most. I turned it on the first setting and would push the button to go to the next setting every 10 seconds or so. Once we got through all 8 options, she said she preferred the constant intense vibration setting. So that is what I left it on. Her cunt was dripping at this point from the experimentation with the plug. I used my fingers to play with her clit and g-spot. I was sucking and lightly biting her nipples, she had another orgasm.
By this time, by cock had sprung back to life. I then asked her if she would like to try my cock in her ass. (We had discussed anal sex before, but she was never fully comfortable with it, but she liked me fingering her ass and also licking her ass at certain times) She said yes, she would like to try it. I asked her what position she would prefer, she wanted to stay laying on her back so she could see my face. I pulled her to the edge of the bed and I stood next to it. I used the lube again and lubed up my cock. I turned off the plug and removed it from her ass. I slowly slid my cock into her asshole, taking it slow to make sure it wasn’t too painful. After a few short pumps, my cock was buried balls deep into her. I then started slowing fucking her ass, she was loving it. Once I was able to really start fucking her ass I used my hand and started rubbing her clit, while she was playing with her nipples. She had an incredible orgasm at this point from all the stimulation and I couldn’t hold out any longer and pumped her ass full of my cum. What an incredible night.
Source: reddit.com/r/gonewildstories/comments/dlct4h/her_first_time_with_my_cock_in_her_ass
Man 3 holes in 1 night you are lucky
Very good story.