I hope you enjoy the story of me being pegged the first time.
I had a girlfriend just after high school that would give me a hand job while rubbing my anus, but she never penetrated me. She did let me experiment with licking her anus but she didn’t enjoy it nearly as much as I did. In college, I had a girlfriend that would put a finger in me when she was giving tipsy blow jobs. She too, let me lick her anus but was very shy about anal play so it never went far. Over the years I found bigger, better toys and found girls that were more and more open to ass play but I never found a girl that was really into it until I met Krista.
I met Krista in my 30’s. Within a few weeks of us dating, she started showing just how much she loved anal play. She would always finger me during blow jobs. She never hesitated to let me fuck her in the ass at any given moment. One night while laying in bed on my stomach, she crawled over to me, pulled me onto my knees and started licking my throbbing anus. It was the best feeling I had ever experienced. She went on to fist me and give me the best blow job I have ever had that night. She and I spent hours playing in each other’s asses, but this story isn’t about Krista. This story is about Rhonda.
Rhonda and I had been acquaintances for a few years and had been on a few dates, but nothing romantic ever came of it. She was lonely one Christmas and contacted me and our friendship started getting a little more sexual. She would drink a lot and send sexy selfies and tell me about what turned her on. She made it very clear, very early on that she loved having her ass worshiped. She wanted it kissed, licked, fingered, fucked and spanked. She also loved rape fantasies and wielding a strap-on. She told me about getting a female friend drunk and destroying this friend’s pussy with a strap on she bought and kept in her car “just in case” she ever had opportunity to use it. Eventually Rhonda and I started seeing each other again and things got very kinky very fast.
Most weekends, Rhonda would stay with me so we could molest each other all weekend. This particular weekend was a little different. When she showed up with her bags, we started where we always started. She came in and found a place to get comfortable with no panties so that I could bury my face between her legs. Some couples kiss or hug when they first see each other. We weren’t really a couple. We said hello by me licking her pussy until she was near orgasm, then switched to me making out with her anus and fingering her until she was cumming down my arm. When she was finished, I quickly disposed of a load into her asshole and we made dinner while my cum leaked out of her. Later that evening, after we had a few drinks and dinner, Rhonda excused herself to use the restroom. I was browsing Netflix for something to watch, when I got a text. The text was from Rhonda and simply said, “Come to the bedroom”.
I walked into my bedroom to find Rhonda in a flesh toned bra with black trim and matching crotchless panties that she new I really liked. She was on her hands and knees but had a thick mat rolled up and placed under her as a sex-wedge. The opening of the crotchless panties was large enough that I could lick and kiss everything with no fabric getting in my way. I knew what she wanted by the angle of her hips and she knew that I could never resist licking her asshole. I found it especially irresistible when I thought I may be able to taste my cum lingering in her. When I moved behind her to start going down on her, I realized that she was also wearing a harness with a double headed dildo. She had also left her panties from earlier in the day laying on the bed beside her. She instructed me to remove my clothing, put on her panties and to start licking her if I knew what was good for me. I happily obliged.
I put on her panties and started working on her. I alternated from licking her anus and probing into her. Then I would move to lick her pussy, pushing her dildo out of the way as much as I could without making it fall out. Her ass was displayed in the air for me to enjoy and my ass, clothed in her too small panties was in the air as well begging for attention. She came entirely too soon from the feeling of being penetrated by her purple silicon dildo and my tongue trying to get into both of her holes.
Rhonda always became aggressive after her first orgasm and I knew what was in store for me was going to be brutal. She would often slap me after giving her head and would then hold me down and ride my cock or sit on my face for her next orgasm. When she finished cumming, she spun around, and grabbed my face and told me I was about to get fucked. She slapped my cock and balls and pushed me down on the wedge she had waiting for me.
I had been fingered before, I’d had my asshole licked before and I had even been fisted before this. This was not my first time to be on my knees with my ass in the air for a woman to give me pleasure. This was, however, my first time having my ass in the air and my face forced into a pillow for a woman’s pleasure. I felt very vulnerable in this position with her ill fitting panties on. I felt very weak from the excitement and alcohol I’d had. I felt helpless, because I knew how rough Rhonda was going to be and I either had to take the abuse coming to me or stop everything at which point she would just go home. I was enjoying this mix of feelings and wanted to make sure she took full advantage of it.
Rhonda slapped my ass before pulling my panties down. She put some lube on her dildo and started wiping the excess from her hands onto me. She wasn’t lubing up my ass, she was just using me as a hand rag. She forced my knees apart to get me to the right height and stretched my cheeks out.
“I’m going to pound your ass out now.” she said, with a condescendingly sexy tone in her voice.
She started pushing the hard, purple, silicon head into my asshole and I could tell there wasn’t enough lube for it to be an easy entry. She was struggling to get it in. I knew if I told her to put more lube on that she would put too much and I wanted it to be a little dry and rough. Instead, I arched my back down so my cheeks would open a little more and told her to spit on my asshole.
She gave a little groan of pleasure at the idea of doing this and worked up enough spit to give just enough lubricant to get the head started. She had never pegged a guy before and was finding it difficult to get the angle of the toy just right to slip in. She had every intention of fucking me hard once she had her cock in me, but she was being careful not to make the penetration painful.
“Don’t be gentle.” I told her and grabbed her dick and pressed it into me.
“You little whore”, she said, “you’re going to get it.”
She started slamming into me. She alternated from holding my hips to pulling my hair. She kept pounding and pounding into my asshole.
“Are you OK?” she asked and I could hear in her voice that she was hoping that the answer would be yes. She didn’t want to stop.
“You’re fucking me so hard, Rhonda. I love it, my ass loves it, but I may need just a little more lube”, I begged her. “But don’t put too much. I like it to hurt some.”
She gave me no lube. Rhonda, as I said before, could be very aggressive and enjoyed rape fantasies. When she was drinking, she had a mean streak. Tonight she had been drinking. I felt her dig her fingers into my hips and push down. She lifted her knees off the bed so that she was perched on the balls of her feet and her hands. She proceeded to bludgeon my asshole with her cock.
She fucked me harder than I have every fucked a girl. She fucked me until my head was pushed into and turned sideways against the wall. My knees had slipped all the way apart and I was almost flat on the bed. My panties were stretched and biting into my hips. My asshole, prostate and colon were raw and sore. I felt brutalized, used and dirty. The position was awkward and uncomfortable and her strokes were relentless and her member came out of me and slid up my crack and back smearing lube as it missed its target.
She took this intermission to pull me back down onto the bed and into position again. I could feel her dragging the head of her cock around my balls and ass to gather some lube on it to continue her onslaught. My asshole was ragged. I knew she had the energy to keep this up and that she would destroy my colon if she could.
Rhonda and I got really rough at times. Correction: Rhonda got really rough at times. Really rough. She punched me in the mouth once after licking her asshole while she used a vibrator. We had established a safe word system like responsible couples should. It wasn’t cute like saying “red, yellow or green” and it wasn’t some bizarre word that one would never say during sex to ensure that there was no confusion. It was more straight forward and to the point. When things went too far, we agreed to simply tell the other to stop what they were doing.
Rhonda was preparing to penetrate my gaped hole again but was not being as careful as before. She didn’t want or need the right angle to penetrate me. She could have used the thick end of a baseball bat at any angle and my sloppy, sore ass would have easily accommodated it.
“No, don’t Rhonda. It hurts. Don’t fuck me anymore, I can’t take anymore.” I said exhausted and started crawling away from her. Like a predator she pounced, forcing her cock all the way in me and resumed her assault.
“Please stop, don’t, I can’t take it.” I pleaded. I started pushing her off and tried to get away. This only made her throw her full weight on me. She held me down and drove her hips against my ass. I could feel her cock deep in my colon and could feel her pubic hair abrasive against ass crack.
“Stop, stop, you have to stop” I continued demanding and fighting. The more I fought and told her to stop, the harder she fucked me.
“Stop, Rhonda, please. You’re raping me. You’re hurting me.” I told her. This sent her over the edge. I knew it would. She pounded harder and harder. When she slipped out, she would unceremoniously shove it back in. She continued delivering the fullness of her dick into my body with as much force and aggression as she had in her hips. I could feel my head bouncing every time she hit bottom.
“Oh, you’re raping my asshole.” I told her. I had given up fighting her.
“You’re breaking me in half.”
She came hard. It was intense and wet and loud.
“I’ve gotta have cum in me right now.” she demanded while switching positions with me.
“Where do you want it?” I asked getting into position. I was ready to cum already and knew it was fine if I blew my load as soon as I got inside her. She just wanted cum in her so she could play with it as it leaked out.
“Shut up and pick a hole before I punch you in the mouth.” was her only reply. She meant it.
Since I already had her asshole that day, I chose her pussy. It was wet, hungry and open from the other end of the dildo being inside it while she fucked me. I pushed the dildo down, and slid easily into her. I could feel her end of the dong rubbing my balls and ass every time I pushed into her. I unloaded into her quickly and crashed onto the bed.
She pulled her gear off and took off her bra and panties. I still had my panties on. She straddled me and sat on my limp cock while we caught our breath. She kept grinding onto me and putting her big ivory tits in my face so I could bite her nipples. She knew I liked kissing her and she would oblige from time to time despite not wanting that level of intimacy as a fuck buddy. She leaned in slowly for a kiss and I opened my mouth to accept her tongue. Instead of kissing me, she stopped short, closed her hand aggressively on my throat and spit into my mouth. She got up and left the bedroom. She had no interest in cuddling or talking. She was done fucking and went to the couch to check her phone. I lay on my bed with lube dripping from my battered ass, cum leaking from my cock and the taste of her margarita flavored spit in my mouth. I pulled my wet panties off and went to sleep.