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The previous story submitted by this writer can be found here: https://www.thecuckoldconsultant.com/contest-stories/jerome-loves-jens-thong/
I got a short text from Jen that morning as I was making the kids breakfast. She just stated “I cashed in my winning bet with Jerome on how long it would take me to get you to cum over the phone last night. I woke up around 2AM and I started to play with Jerome’s cock! It only took a couple of moments before it was engorged and sticking straight up! I went under the sheets and slowly took his cock head into my mouth and moistened the thick head. After a few moments I got up on my big black stud and started slowly rubbing his cock head against my pussy lips until my juices started flowing. I whispered to Jerome “i’m gonna fuck you now”!
Then with just an adjustment in my hip angle and a little pressure, I was able to slip his cock head into me! I let my pussy adjust to his girth and then slowly started pressing down a little with each thrust. As I got him half way in I leaned down to start french kissing my young stud. I buried the rest of his length into me as my tongue was in his mouth! Once he was fully in, he finally grabbed my ass and I felt his strength hold me buried onto his cock!
Then we started moving in rythm. We were no very used to each other’s wants and needs. We knew how to drive each other crazy with desire. He mentioned how hot I was last night. We laughed about drawing a crowd as we fucked hard in the back of the bar.
I asked Jerome how he was enjoying the vacation as we fucked. He said he could have never imagined this when he was 14 and in my class, watching my ass from behind as I taught the class by writing on the blackboard! I said oh, you like my ass huh! He said, oh yea, that was one of my fantasies as he slapped my ass and buried his cock deep into me in a powerful thrust!
I said “ and what was your fantasy”? He said, well like I said it was just one of my fantasies. You have already made a lot of them come true over the last several weeks!
Jen said “we’re they as good in real life as your fantasies”. Jerome said “way better” as he picked up the pace. We just fucked for a few minutes before I asked “so what is your fantasy about my butt”. As Jerome buried himself in me one last time, and started to explode deep in me, he said “I wanna fuck that ass”!
I should have known that’s what he meant, but as he said it and came in me I got both excited and a little scared but whispered in his ear “we could try”! After I said that, I got wet, and Jerome was able to stay hard long enough for me to finish on top of him with an orgasm of myself!
I could not believe what I read! Jen just left me hanging with the thought of her offering Jerome something I never got during our marriage, a chance at Jen’s ass!
Anyway, I went about my day getting the kids ready, going to work, picking them up from work, dinner, dishes, etc - all the day wondering if they would go through with it???
After I put the kids asleep my mind started to wonder. I started thinking of all their sexual escapades on the vacation I am paying for them to enjoy. I wanted to masturbate but i knew Jen told me not to. I was hoping I would hear from her and she would walk me through my masturbating again.
Before I was about to fall asleep I finally got a text from Jen describing their day and the fulfillment of Jerome’s next sexual fantasy!
Jen started with a surprise she got after she took a shower that morning. Jen said apparently Jerome had come prepared! Jen said “After I got out of the shower, Jerome showed me what he brought me “A butt plug and some anal lube”! Jen said she just said “OMG, you are so bad, and gave Jen a playful soft slap! Jerome said “if you are open too it, this could help you prepare and enjoy it more. Jerome said the is no pressure, if She didn’t want this, or was uncomfortable or in pain, they would stop immediately”. But if she was interested that she could put this in herself later today, we could walk around the town, look around, shop, etc - whatever she wanted. Then later when they get back, we could try something new”
So Jen said she agree to try. After a morning longing at the pool, they agreed to go have lunch in town. Jen took the toys into the bathroom, lubed up, and after a few minutes slowly slide the butt plug in. It felt foreign and strange but did not hurt. She put in a pad and some panties and then some comfortable shorts and stepped out. Jerome went over and gave her a big kiss. He slipped his hand down to Jen’s ass and gave a feel. He could feel the butt plug”! Jen giggled and s playfully slapped Jerome again. Jerome just said “nice” with a devious smile!
They went into town. Every so often Jerome would grab Jen’s ass and give a feel. Jen said it felt funny ever time Jerome noticeably try to feel the butt plug. Jen said sometimes it seemed he was trying to move it around a bit! But it started to feel good!
At lunch Jen said she had trouble getting comfortable sitting down. Jerome noticed her squirming around a bit. Jerome asked if she was OK and just suggested to stop moving and just try to get used to the pressure.
After lunch they walked around and shopped a bit. Jerome picked out a low cut sheer top for me. I picked out a nice watch for Jerome. Jen said “thank you hun to me”!
Then Jen said when we got back to the hotel room, Jerome could not keep his hands off me. Of course he went right for my ass. This time as he felt my butt plug through my shorts he started rotating it though my shorts and so started moving my ass in circles for him.
He said “i can’t take it anymore and pulled my shorts off”. He laid me in my back and slowly rubbed his cock against my clit. It was not long before he was pressing his cock into my pussy. I could feel his cock in my pussy and the butt plus in my ass as he thrust into me. It was a great feeling.
When he pulled out of my pussy I started to get nervous. Jerome gave me a kiss, and turned me over. He slowly pulled out my butt plug with a plop! He used a towel to wipe me down. I could feel his huge cock head against my ass hole as he started to press down on me. OMG Doug, when his cock head popped in my ass for the first time my legs were shaking! It was both pleasure and pain like i have not felt before. But Jerome was great. He took his time - asking me how i felt as he pushed each inch into me. After i recover from his first full depth entry he slowly started his rythm as he stroked into me! He whispered “Jen your ass is better than I ever imagined as he picked up his pace. Later he said he knew it should be quick the first time, and he picked up his pace and eventually exploded deep in my ass! He slowly pulled out and I could feel his cock resting on my ass as he gave me a kiss and comforted me.
We then both went to the shower and he lovingly lathered me up and washed me down. I then washed him down making sure I cleaned his cock well!
I could not believe what I just heard! Jen had just had her first anal sec with her big black stud who had been her student from 10 years ago!
I could not help myself as I masturbated to reading the story again. Then I had to go clean my own cock!
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