Years ago, I had an affair with an older man. Henry was his name and he was fifty-seven. Many people would not find Henry classically handsome if they ever saw his face walking down the street, but he was tall, lean and built right. There was also a cheerfulness in his eyes that complimented his thin white hair and clean face. He had a way of talking to me that I found gentlemanly and devilish at the same time. I guess when men, some men anyway, get to a certain age they develop this firm way of speaking that I find incredibly attractive, at least with Henry I had.
I am five-foot six and Puerto Rican. I have dark hair, brown eyes and a honey-tan that could only be inherited from Boricua parents. My facial features are small and regular and about what you would expect from a Latina. My bottom is round and still decently perky. My chest is a welcoming 36C with brown, round nipples. I was thirty-three at the time.
I was also married, Henry was not. He had divorced long ago and lived alone in a roomy house not far from my own home. We had met while jogging in a nearby park months earlier and grew to know and like each other as circled the park. We were friends first until our relationship evolved, landing me in his bed several times a week.
The first time Henry and I had tried anal, we were about two months into our affair and a few weeks away from Christmas. One day I was visiting house, coming in through the kitchen door, as he had grown accustomed to leaving it unlocked for me when he was home. It made our affair easier not having to ring the bell or come in through the front door. I had gotten very good at sneaking in and out of his house stealthy enough so as not to draw attention. I'm not naive enough to think a nosy-neighbor or two never saw me my comings and goings around Henry's yard and didn't catch on, but it had made me feel better to sneak-in the backdoor. Besides, Henry and I never got caught by the people that mattered.
One day, weeks before Christmas, I had seen his next-door neighbor parking a car in the driveway. I just continued walking without stopping. I came back around not long later. I only had a few minutes before I was expected home, but I stopped at Henry's house to say hello and maybe for some heavy petting. I found Henry sitting in the living room with a gift in his hands after I had happily found his back door unlocked.
The gift was small, square and wrapped in red with a blue bow on it. Henry was sitting on this ugly, Camelback sofa that I hated. "Come here," he said when he saw me in the doorway and patted his legs. He wanted me to sit on his lap. Just being careful, I first checked to see if the curtains in the living room were still closed before I went to him, like they had been from outside.
They were closed.
"Hi," I said smiling. I was wearing dark jeans with a hooded cardigan sweater and heeled boots. It had been cold. "What's this?" I said referring to his gift as I approached and wrinkled the legs of his trousers.
He put one of his hands on my knees while the other held the gift. He kissed me. I had grown to crave for his lips. His tongue was always perky and its piquancy made me flush. When we were done, he made a gesture for me to take the gift and open it.
"Thank you," I told him as I opened the box. He had bought me a silver link bracelet. I kissed him again. I felt wetness in my panties as he took the bracelet out of the box and locked it on my wrist. "No idea how I'll explain it," I told him looking at it. I was talking about what I would say to my husband regarding the present. I obviously couldn't say where it came from.
"You found it on the street, your grandmother gave it to you, you've had it for years and just began wearing it now," Henry said listing reasons. My husband actually never noticed it.
I admired it for a bit and then looked at his brown eyes, I was embarrassed about what I had to say next. "I wish I could get you something," I started and he stopped me with a warm kiss before I could finish my sentence explaining my finances. At the time, I had just begun working part-time, I had lost my full-time job at a hospital earlier in the year. I was a nurse and my new job at a public clinic didn't pay me very well. My husband and I were making our bills on time, but things were tight, especially with our daughter's private school bills. I couldn't afford to buy Henry anything.
Henry's hand began traveling from my knees the top of my bottom, over my jeans, while I sat on his lap. He had a smirk on his face, "I know something," he said.
"No!" I complained and darted on my feet in front of him. I knew what he wanted. Henry wanted anal sex. I hated anal sex. I've had it a few times in my life before then, but never found much pleasure in the act, only wildly discomforting. The last time before that, as I recall, was a year or so back with my husband. We had just come back from seeing The Aviator and I vowed to myself afterwards never to do it again. I wasn't talking about the movie.
"Joking," Henry said laughing and then pulled me back down to the couch with him and we began dry humping.
Later that night, in bed at home watching television, I thought about my conversation with Henry and his request. He had first asked me for anal right before our second time ever together. I told him no straightway and he left it at that. All my anal experiences had been some of the most uncomfortable moments in my life, but in bed that night with my husband sleeping next to me, I began pictured all the things Henry had done to my body.
Henry had kissed me better. He had groped me better. He had ate my pussy better, he had fucked me better. He had even looked at me better. I slept well picturing Henry's face and wondered if maybe anal sex wasn't that bad of an idea. My last thoughts that night wondered about giving him a chance at the thing I had promised myself I'd never do again.
A few days after, I was naked in Henry's bed with my face at his hairy crotch. My tongue battled his dragon with nothing but saliva and precum. My right hand was holding the top of his shaft at the head, while my left fingers tickled around his balls and pubic hair. Henry was lying down with two pillows propping his head up so he could see me. I jerked his reptile away from me towards his bellybutton and licked the bottom near the crotch forest, then I slid my hand down the tilt and reached my mouth up to sample the top of his circumcised cock. I looked up at Henry as he looked down at me. He parted the hairs from my eyes. Henry was opening my world up. I wanted to return the favor - and maybe pay him back for that bracelet - so I brought up the anal request.
"I've been thinking about something," I told him. I put his prick in my mouth to drain it. My head bobbled up and down eating his cock furiously. My finger curled his pubic hairs like I was playing with my own hair.
Okay his nod and eyebrows suggested. He didn't have much breath to talk with, he was close to exploding.
