My First Good Anal Experience

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.

I stopped cuddling his grass and patted my bottom twice. Clap, clap it sounded. He saw what I did and understood what I meant right away, "Yeah?" He asked straining.

My mouth inhaled Henry's cock all the way down to his crotch, Henry wasn't very big, but his hands had started forcing the issue with my head. His dragon blew. Henry cursed at the air and let me go. His milk spilled out my mouth as I coughed it out. I could have swallowed his sperm, but I choose not to this time. Henry had a heavy load that didn't particularly taste good, but I never told him that. I just let his sauce stain my chin and then cleaned the mess with his pillowcase.

He took a minute to compose himself and catch his breath. I stayed where I was face down on the bed but no longer had his manhood at my eyes. Henry sat up and asked me plainly, "Can we now?"

I had actually been hoping we put it off for another day. Some distant far-off day. Months maybe. I had already regretted bringing it up then, and I wanted nothing more than to take it back. "Today?" I returned worried, lowering my face so he wouldn't see my doubt.

"Why not?" he asked and left the bed.

I turned over and looked at the ceiling, "You just came," I said almost pleading. I sat with my knees up and hugged my legs. My eyes followed Henry as he traveled to a desk by the bedroom door. His flaccid member and sack bobbled from side to side. He opened one of the drawers. I knew what he was getting. A Levitra pill. One of the many Viagra clones. My brain was running around for excuses, but I couldn't think of any that would get me off the hook. I had already told Henry that my husband didn't expect me back for hours. I saw the stupid shape of the pill between his fingers as he raised it up to me. He stared at me with those pleasant, browns eyes that I didn't want to disappoint.

I just nodded trying to smile.

He took a few steps to his left and went inside the bathroom. I heard the water faucet running. He came out seconds later drinking from his cupped hands. I assumed he had already taken the pill in the bathroom. His face was stretched with excitement and a smile, anyone could tell he was looking forward to it. I think Henry saw worry on my own face that moment because he began telling it wouldn't be that bad. He walked towards me.

"Hun," he said taking my hand, it was a reassuring pressure. "I'll go easy, I promise. Don't worry". I tried to do as he asked, but I was dreading it. I couldn't help it. Henry looked at me with doubt, for a second I thought he might change his mind and let me off the hook. "Come on," he said instead. He led me to the bathroom. He slid the shower curtain to one side with one quick flick of his wrist and told me to stand in the bathtub. I did. He turned on the shower head.

"Mierda!" (Shit) I cursed. The water coming over me was very cold. It made me shrink away to the wall tiles. Henry apologized and adjusted the water valves, testing the temperature with graces. When he was satisfied, he signaled me back into the rush of the water. It was better, warmer, I felt like I could stay there all day and was hoping that's just what would happen.

Henry's broad, flat hands began running over my curves as the water poured down. He just traced me for a while like he was testing fabric, wondering if he should buy me or not, next he grabbed a bar of soap and helped himself to lather me in determined, heavy movements. His hands soaped my neck, shoulders and stomach. They tossed my hair back and scoured all over my chest with the white bar of soap. He slipped some of his freckled fingers under my right breast, squeezed tenderly as he passed, and didn't stop groping it until he was satisfied he had built enough foam. It took him a while. My nipples were saluting him as he did the same to my left breast. "Turn around," he told me. I turned away from him and faced the tiles.

The wall tiles were blue and dingy. Henry commenced on my back. It was exciting having foreign hands bathe me like that, it was a first for me. I had been in the shower with my husband before, but never like this. Not with anyone. I didn't know where Henry's touch would go next and was thrilled every time he made a sudden drift or quick halt. The determination in his mission to scrub me was fascinating. His hands ventured down my back. I hugged the wall and arched my ass. I began experiencing sluggish circles at my rear like he was waxing a car, then he opened my ass cheeks and slid the bar of soap far down my crack and then up again, repeatedly, as if he was doing his laundry on a washing board.

My heart raced.

"Turn," he said again and I turned about facing him. I saw his cock was erect and aiming right up. The pill had made it formidable. Henry was soaping my tummy again as I admired his pole. He had used the pill only once before in our love making, a few weeks ago he had wanted to 'get another fuck in me' before I had to go home, but his anatomy wouldn't let him. So he had taken one of his chemical friends. He was embarrassed to take it, but we had a good time. It had been long and hard and sweaty. I cowered thinking about the damage a Chemically-filled cock would do to my fanny, because it had destroyed my pussy.

"Turn."

He scrubbed down my legs with the soap until they naturally landed at my lower lips. The combining texture of his fingers, the water and the suds swelled my clit to match the size of the tip of his finger. I wanted him to stay there, play with it a bit, but instead he put aside the bar of soap and let the water rinse down on me. He was all business. I tried playing with it myself, but he slapped my hands away.

The white foam sponged lightly down my stomach and legs until they circled the tub drain. It wasn't going fast enough for Henry, so in downward motions he began helping the suds off body.

I was at his mercy.

At this point he was turning me around himself. He rinsed the soap off my back and shoulders and then turned me. He took his sweet liberties clutching my breasts for the sake of his mission and turned me. He opened my ass cheeks and I felt the water sinking down that trench. Purifying me. It was beautiful how he cleaned me. When he was done, he helped me out of the shower and patted me over with a towel several times until I was dry all over. Then he dried himself as the water had also soaked him.

"There," Henry told me and kissed my cheek. He let the towel drop in the wet bathroom floor and we went back to the bedroom. "As comfortable as you can," he told me to position myself on the bed. He left the room saying he needed something. I wasn't going to be comfortable any way we tried it, so I just laid on top of his sheets with my legs sticking out the side of the mattress. My face was looking straight at the casement windows. My legs pointing to the bathroom door. My hair was still plenty wet and it was dripping on the bed linens.

I waited.

The lingering made me a coward, I wondered how fast I could put my clothes on and run away before Henry came back. He would understand, I told myself, but next I heard his feet running up the stairs, closing the door and then approach me from behind. My escape plan was ruined. I couldn't see him and he didn't touch me. I was scared to look. It was like that for a while until he began parting my ass cheeks, I felt myself puckering out of reflex.

"I'm not going to yet," he said and told me to relax. He started stretching my anus with one of his fingers, knuckle deep. It felt slick and greasy, not at all like the water. "Vegetable oil," he said, explaining how he had dabbed his finger with it.

He stretched my hole with that slimy tentacle, dangling it around my anus in a way I recognized. It was the same wicked swabs that I had grown to love on my clit. I then felt a rush of greasy liquid pour over my ass. I turned my neck to spy and saw he was almost emptying a bottle of oil. He was very generous with it. He massaged my cheeks while grabbing fistfuls of skin. He parted them open. He lubed the inside with a heavy stream of oil until my body absorbed it. I felt a tongue at my anus for a second, but he took it away quickly and replaced it with two fingers. He stretched my anus again, but this time it made a prickling sensation that me squirm. It wasn't bad, I liked it. I was hoping that's as bad as it would get, but then his fingers went away again and I got nervous.

I sensed the moment was coming.

But nothing happened for a while, I just caught the sounds of the street coming from the window. I felt the building mess of the wet sheets under my arms as my hair kept drying. I started feeling something on my rear.

I knew what was happening.

Henry was slathering his cock across my ass cheeks from side to side like a painter with a brush, building anticipation that I didn't feel was necessary. It just made thing worse. I couldn't see his face, but I knew he had to be smirking.

Bastard.

His cock was way too firm, I ran my fingers through my hair in frustration as I pushed my torso up with my elbows. Next, all at once, not entirely out of nowhere, the tip of his member began leisurely trespassing past my cheeks. All my muscles cringed. My hands reached up for the edges of the bed but they were too far away to reach. I tugged at the covers instead. His instrument was moments away from digging a deep grave

"I changed my mind, I changed my mind!" I told him and crawled up on the bed away from him. I meant to jump out the other side and throw myself from the window if necessary. I didn't even get half-way. I only managed to place my legs completely on top of surface of the mattress. Henry had kept me in place with a speed that could only have come from jumping on top of me. I felt his weight cover me all over, his arms at my arms, his chest at my back, full on as if a bomb was about to explode behind us.

"Mary," he said pressing on top of me. He called me Mary sometimes instead of Maria. I had told him that's what most of my friends called, Mary. He had wanted to be my friend. His voice was soft. "Relax, Hun, please. I promise it won't hurt."

"I don't want to do it," I pleaded with him leaning my head up, trying to make him look at me. I struggled to pull and wriggle myself out. I felt his hardness poke at the bottom of my back and his balls rest right below that at my cheeks. His penis was so firm, rough and brutal.

"I'll go slow, please" he promised me. His voice sounded desperate. It made me sad.

It made me think about how it was all my idea. I had brought it up that day. I had basically promised Henry I would do it and then he had taken the pill because of that promise. Worse, convincing myself, my mind was still early in that part of the relationship when you just want to please and come off as adventurous, so I gave up. "Fine," I told him, "Do it."

He eased off my back slowly while keeping his hands pressed on my back, as if he didn't trust me to stay in place. I felt his touch get lighter until he descended to sit on my thighs. At that moment, I truly wished I had not gone to Henry that day, and then I felt IT.

It was worse than I expected even with how gentle he inserted the meat. He trespassed past my cheeks tenderly enough, I guessed, but then the pressure I felt as he stabbed past the first ring was rough, the second was even worse. Husband cock, Henry cock, my ass couldn't tell the difference. Anal still felt strange and foreign and very, very unnatural, even with my lover. It hurt. I started moaning quietly and leaned my breasts down, resting my forehead on my wrists. But I took it all for him. I wanted to be strong for Henry.

"Relax, hun, relax," he kept saying as he pushed himself in and out slowly. His weight coming on and off my thighs as he filled and emptied my ass. He had kept one hand on my rear to keep me from running again, while the other I felt gracing past my right hip as it compressed the mattress down. I could have crawled away then, but I stayed in place. I was doing it for Henry, I said to myself, just once and never again. Just for a few minutes and then I'll tell him to stop.

Henry's motions were gentle as if he was trying not break me, but it was a hopeless endeavor. He was breaking me. I was experiencing the hellish pulsation of his piston with every stroke. He had broken his promise. I wanted to sob and cry. I stayed strong though and somehow didn't weep. My arms reached for the edges of the bed again and this time they were close enough so that I could hold on. Henry was evil, I thought grasping, I hated him. I could feel my body tense and rejecting everything.

"Hun," I heard his lying mouth say, "Please relax." I tried to say okay, but i just nodded. I was seconds away from ending this sick experiment, but then he took pity. Maybe he felt sorry for me.