My name is Jenny and this is the story of how I cheated on my boyfriend. Never in my life have I cheated on any boyfriend, I don’t see the need. If I want another, I’ll break up, then pursue. However, on this night I lost my willpower and cheated on the man I’ve loved more than anyone else. All my past loves seemed like puppy love compared to Trey and it breaks my heart that I did this to him.
I’m a 5 foot 6, twenty-two year old woman with dirty blonde hair and dark blue eyes. I weigh 125lbs and my bra size is 34b. I’m a sexual woman, to say the least. I like taking risks, I like public affection and I like experimentation in all forms including sex. I’ll try anything once. Here is a pic of me.
https://drive.google.com/file/d/1Eo3bZQl8l2pnbOfEijY_uI5_l6L5cx3B/view?usp=sharing
Trey is twenty-five years old with gorgeous long blonde hair, normally tied up in a messy manner. He has a thick unkempt beard that I love. He’s an artist whose main skill in painting and up to this point he’s finished and sold two paintings of me. He’s so good that he makes enough money from it to not have a job but he’s still a struggling artist, living paycheck to paycheck.
The first painting he did of me was as a naked angel. He made wings that I posed in front of and it came out so well I was sad that he sold it. The second was of me and another woman wearing work clothes like the famous flexing woman from World War Two. We posed in a factory, me with a sledgehammer and the other woman with a drill in hand. That painting earned him more money than any single piece of work he made before.
For the last week, Trey and I had been staying at his parent’s house while they were on vacation in France. His parents were due back late tonight as we were supposed to pick them up at the airport. However, today we planned on taking advantage of the opulent house while we could. We planned on having a small pool party in the summer heat but everything changed when inspiration struck Trey early in the morning. When Trey has an idea, everything else is put to the side so we canceled the party.
He wanted me to pose with an old black man and have a contrast of not only skin but age. We went shopping and bought a new skimpy blue bikini and a pair of old school roller skates. He dropped me off at a hair salon to get my hair, nails and makeup done by a woman he’s used before for his models. My hair was done in high and thick pigtails. At six in the evening, Trey returned with an old black man, I have no idea where he found him or how much money he was paying him but he was a very tired looking man with bloodshot eyes.
At 72 years old Roland looked even older than that. He had thick wrinkles on his face that some dog breeds have and a bald head. He looked tired and had a potbelly many older men do. I found it difficult to understand him with his thick southern Ebonics accent but he seemed like a pleasant old man. He had a day worth of gray hair on his chin line and thick lips.
As I spoke with Roland, Trey rushed around getting everything set up. He brought outside an old Victorian sofa and put it inside a cage gazebo with grapevines growing all over it. He set up his easel with a barstool before it and behind that a table with all his equipment. He had Roland sit on the sofa with just his boxers on and I came out with my roller skates, blue bikini and pigtails. Roland didn’t seem to even notice me. Trey gave me a lollipop to suck on and told me to sit on Roland’s lap.
My back was against the arm of the couch, keeping my back straight up. My butt was just below Roland’s knee and legs extended down the couch. Roland’s left hand rested on my lower thigh and his right hand on the couch arm behind my back. Trey put a coffee table before us and put a bottle of red wine on it with two glasses filled. Posing for a painting is boring as all hell and an exercise of patience. We were allowed to move and adjust to keep comfortable and if Trey needed us back in the pose he would let us know. Roland was told to look tired and I was told to look wide-eyed and energetic. Roland and I drank wine and chatted while Trey stayed silent behind his easel, periodically spinning his stool around to get different paints or brushes. Old Mo-Town music played per Roland’s request on the high-end outdoor speakers and a cool summer wind blew about us.
About an hour into it Roland and I ran out of things to say which was fine by me cause I only understood about half of what he was saying. We took a few breaks to stretch our legs and I playfully skated around the pool as the guys watched me. We settled back into our pose as I began to get impatient. So damn boring.
I closed my eyes, ran my head in circles to stretch out my neck when I saw it. My eyes opened wide and my mouth did as well. Roland had his cock fully out of his boxer shorts running up the length of my thigh. It was behind my legs so Trey could not see it and I’m not even sure if Roland knew it was out as his facial expression looked no different then before. It was by far the biggest and fattest cock I have ever seen and looked to be almost a foot long and as thick as an arm. Its base was at my knee and it came all the way up to my hips, I was astonished. I looked away and looked back, still not knowing if this was intentional on Roland’s part. I felt my body heat up and even had trouble breathing right.
“Can you face me honey?” Trey said and his voice scared the hell out of me.
I turned and faced Trey with butterflies in my stomach, looking back out of the corner of my eyes at Roland’s cock. Trey spun around on his stool turning his back to us and right as he did Roland slowly caressed up my leg to my inner thigh and I now knew he had his cock out on purpose. To my utter shock, he didn’t stop at my thighs. He grazed his finger right over my pussy, right over my clit and put his hand back on my knee just as Trey spun back around again. His fingers just barely touched me but it sent bolts of unwanted pleasure throughout my body.
I turned and Roland and I made eye contact. He looked so old, so sickly with his red eyes. I was disgusted but yet that giant cock and the tingles of pleasure he just sent through me gave me such a conflicted feeling I never had before. Trey turned again so Roland ran his hand to my pussy, grazing it once again as he put his hand on my back and softly caressed. From my knee up my inner thigh to my pussy he softly touched me three times, grazing my pussy each time. I was beyond aroused, beyond disgusted.
Trey turned back around so I grabbed a glass of wine and chugged it. I don’t know why I didn’t say anything, the very idea of calling him out didn’t even occur to me. I just kept peeking back at that giant black cock. I’ve never been attracted to black guys and still wasn’t with this old worn down man under me but I always liked risk and daring sexual endeavors. I don’t mean to sound full of myself but the thought of this gross old black man with a woman as good looking as me seemed…erotic to the extreme. I wished Trey would turn again just to see what would happen but he didn’t for so long and we just sat there awkwardly. Time moved so very slow as dusk settled in.
“I’ll be right back, need to grab some paint,” Trey said.
The second Trey stepped foot into the house Roland slightly lifted my legs and pushed his cock under me and in between my legs. It’s massive head pressed right on my pussy on top of a wet spot that was forming. As if it was no big deal at all, Roland nonchalantly pulled my bikini bottoms to the side and pressed the massive head right on my pussy lips.
“Mmm…Mmm.Mmm. Do you want it inside?” Roland said.
“No,” I managed to say.
Trey came back out with his paint. I had no idea if he could see what was going on but when he sat with no reaction I looked down at this amazing cock and couldn’t take my eyes off it. The tip of it was getting wet with my juices and every subtle movement we made caused a tiny bit of friction between us. Sucking on the loiipop my mouth was almost overflowing with saliva and sugar, I had to keep swallowing to prevent drooling. I don’t think I was ever more turned on and then I would look at his face and cringe with disgust.
Trey spun in his chair and Roland immediately took his cock in hand and began to rub the head on my clit. Little strains of my pussy juice connected his head and my clit as I covered my mouth, looking at Trey then back down at his cock. Trey spun back and Roland quickly went back into position and as he did his cock slipped down and the very tip of it slipped inside me. I moaned and immediately coughed to cover it. He was just a half-inch inside me and my entire body quivered as goosebumps rose all over my skin.
“Jenny can you put your shoulders back more please,” Trey said.
Again his voice scared me. I pushed back my shoulders and looked down to see my nipples harder than ever, poking through the bikini top. Trey spun around.
“Can I?” Roland whispered.
“No,” I whispered back.
He took his cock in hand and again rubbed it on my clit and it was like some outside force took over my body. I reached down and put it inside me. My eyes rolled back and I bit my lip to stay quiet as I looked at Trey, waiting from him to face us again. His cock filled me and I felt juices being pushed out of me and run down to my asshole. I looked down to see not even the entire head inside me yet. For the first time in my life, I had a black cock inside me. First time I had a senior citizens cock inside me. First time I cheated on a boyfriend and in front of him no less. First time I ever fucked a man before a first kiss. I was totally and utterly disgusted with myself and never more turned on.
“I need to take a leak, be right back,” Trey said as he spun and got up.
I leaned forward and put my legs together tightly so Trey wouldn’t see. I pretended as if I was about to get up as Trey walked away and when he entered the house I leaned back down. Roland began to fuck me and I spread my legs a bit giving him more access. I moaned into the summer night.
“It’s so big…Jesus,” I moaned.
He kissed me which skyrocketed my level of disgust. He smelt like an old man, he tasted gross like old cigars. Instead of shying away I kissed him harder and more passionately as he fucked me with slow and steady thrusts. I was filled, entirely and then some when I looked down to see him fucking me with only half his cock. With his thumb he began to flick my clit and I couldn’t believe it when I began to orgasm. I covered my mouth and moaned loudly, never cumming so quickly before. Trey opened the door and walked out as I was still cumming. I turned my head away from him knowing I couldn’t hide my flushed face and I felt I could no longer hide this from him. To my surprise, he noticed nothing with Roland’s cock still deep inside me.
For five minutes we sat still until I noticed Roland’s eyebrow furl. A moment later I felt him shoot his load deep inside me, something I didn’t even let Trey do. The next time Trey spun around he pulled out of me and I fixed my bikini bottoms, putting them back over my pussy.
Later I made an excuse not to join Trey in picking up his parents and I went home. I felt horribly guilty and disgusted I let an old man cum in me. I love Trey so much and even was beginning to think about marrying him but now I betrayed him. I just felt like shit.
The next morning I was feeling even worse. As I zoned out, starring at nothing in my kitchen I drank coffee when I heard the doorbell ring at 8 am. I answered the door and to my surprise, Roland stood there. He let himself in, pushed me against the wall face first and pulled down my shorts.
To be continued, maybe
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Do you happen to have a picture of the painting?