I don’t think I will ever forget the time I was caught having sex with a girl named Gretchen. Gretchen was a cute, very pale girl with dark rimmed glasses. She was around 5’6″, skinny, long straight dark hair and looked amazing in the pair of jeans she was wearing. Her ass looked so hot and even better when she was naked.
We met through a friend of mine and a girl he was seeing. Gretchen and I were setup by them. We happened to meet up at Gretchen’s apartment where she lived with her mom. My friend and I happened to show up just after her mom went to work late one evening just after 9pm. Her mom was a nurse and usually worked the night shift. Gretchen and her friend were having a sleepover. I was sixteen at the time along with my friend and Gretchen and her friend were fifteen. My friend and the girl were seeing sat next to each other on the couch and he began to fondle her in front of Gretchen and I. They started making out and it kind of made us feel uncomfortable. Gretchen and I moved around and into the small kitchen area and she stood leaning against the stove and I against the refrigerator. Our conversation was choppy at first while we both scoped each other out. It wasn’t long before Gretchen’s friend asked if she could use her bedroom. I was surprised how causal Gretchen was when she said sure. So my friend and his girl went into Gretchen’s room and it wasn’t long before we heard them having sex.
I hadn’t developed any game yet and Gretchen seemed to be comfortable with being forward when she asked if I wanted to make out with her. I liked that she was into it and I moved into her and we began to kiss. Gretchen had soft narrow lips and our tongue began to dance in each others mouth. Her hands squeezed my ass. I ran my hands down on hers as well. I was so easily aroused and was super hard when she ran a hand over my crotch area. When she felt me, she jumped back and gasped staring down at the large bulge in my jeans. I was only an inch taller than Gretchen at the time. I was very lean so what I had between my legs looked quite impressive to her. I almost told Gretchen my first also reacted to me the same way but was smart enough not to say it. Instead, I asked Gretchen if we could go into the other bedroom. Gretchen just nodded and grabbed my hand leading me. I closed the door behind us and in the dark, we began to help each other out of our clothes. I had gotten Gretchen down to her tiny bra and skimpy panties. I was shirtless and my jeans were down around my ankles. Gretchen went to her knees and pulled down my underwear. When my large extra thick cock sprang out and slapped her in the face. Gretchen yelped from shock and fell backwards. She scrambled back up against the nightstand and frantically reached up and turned on the lamp. Her eyes got huge behind her dark rimmed glasses and her mouth opened wide. I stepped out of my jeans and underwear and just stood there kind of enjoying the spectacle Gretchen was making. I jumped a little and Gretchen’s whole head bounced along with my cock as it stared right at her. It was a long minute and I asked if she was going to show me since I had shown her. She stood up shaking and removed her bra first. Her tiny breasts were kind of pointy looking and her nipples seemed to be the biggest part of them. I liked how erect her nipples were and how firm her tiny breasts looked as she inadvertently tried covering them up. I smiled very pleased with her lean body and pointed to her panties. She slipped them down still admiring me. She had a sexy cute bush just above her beautiful slit. Gretchen had her legs together but right below her pussy was a little area where light shown through her skinny thighs, it was very hot. I walked up to her and she sprang into her mom’s bed under the sheets. I turned off the lights and joined Gretchen.
It was an understatement when I say how nervous Gretchen was when our naked bodies touched. Her breathing was fast a and shallow as I began to kiss her. I made my way down to her neck as she timidly touched my cock. My cock jumped and throbbed with her light touching. I wasn’t so timid with my hands as I rubbed her clit hard. I slipped my middle finger into her slit and she moaned and twitched. She never asked for me to use a condom and so I thought she was cool with it. I moved on top of her and rubbed my cock up between her legs. Gretchen moved her hands down on herself and rubbed. She pulled herself open as my tip had found her spot. I pushed in and was met with a surprisingly tighter fit than expected. I thrusted my muscle into her harder and felt my tip penetrate into Gretchen. She let out a painful moan as her hands reached to squeeze my narrow hard ass firmly. She was almost panting like a dog when she tried to ask if I was all the way in. Her legs slid up and down on either side of me. I cupped her tiny round tight ass with both hands and plunged in deep. Gretchen cried out loudly then groaned quietly realizing how thin the walls were in the apartment. I held myself buried inside her and amused myself by how huge she made me feel. I whispered under her fast breathing asking if she acted this way with all her boyfriends. Gretchen winced and shook her head making a “un huh”sound. I took another deep plunge into her as I leaned into Gretchen. She again cried out but seemed to enjoy it a little more. Over and over I took long slow deliberate strokes into Gretchen. I also leaned more over her and her legs now were up over her head with the help of my arms positioned under them. The covers were off of us and my ass felt the chill air. Gretchen had her arms out to each side as she grasped pillow tightly. She continued to make loud noises with ever pass deeply into her skinny body. Just as I was increasing my pace, the phone rang. It was in the living room. Gretchen seemed to be into it and so it just rang until it stopped. The pounding began. Gretchen moved her hands away from the pillows to my ass. Her eyes now looked into my blue eyes and her legs were pushed up higher. The bed began to squeak louder. Gretchen was now moaning as her pussy was being stretched wider and deeper.
Then in a crazy turn of events, the door burst open and the lights were turned on. I had never heard someone yell so loudly! Her mom was aghast! ! Her face was pale and her cheeks flushed, you could feel the anger. Gretchen kicked me oft of her as I jumped off the bed. My cock was super hard and covered in her goo. Her mom looked directly at me. She grabbed her chest and fell back against the wall when. She saw us. It only turned me on more as her mom clutched her huge chest area. For a moment there was silence. Gretchen’s mom swallowed hard and spoke as calmly as she could for me to grab my clothes and get dressed in her bathroom. I did so quickly. Gretchen and her mom erupted in a heated argument. I struggled to stuff my hard cock into my jeans having to leave the top button undone and pulled my shirt down to cover my tip. I made eye contact with Gretchen and without a word I bailed out. At that same moment my friend who only had his pants on with the rest of his clothes in hand ran out with me. We scrambled around behind some bushed along the apartment complex and he got dressed. We then tore off until we got a few blocks away and shared our stories.
Days later, the story broke and my friend and I were grounded but it didn’t stop us from seeing the girls. Like most young romance, Gretchen and I split up as did my friend and the girl he was with at that time.
Years later passed, and the oddest thing happened when I went to visit another friend of mine at the hospital. My friend was involved in an accident. Fortunately, he only suffered a broken leg and wrist. I was hanging out with him and giving him a hard time when the doctor came in with a nurse. Immediately, I shut up and stared. The nurse who also recognized me opened her eyes huge. The doctor did his shpeal as we just looked at each other in complete shock. It was Gretchen’s mom!!
It had been almost ten years since that fateful encounter of being caught. I had grown a few more inches taller and more muscular. I wasn’t bulky just put on more lean muscle. My friend noticed the strong staring contest I was having with the nurse. The doctor left with the Gretchen’s mom, Jennifer or she went by Jenny on her nametag. My friend asked what had happened and so I shared the story. Jenny had put on a few pounds. She seemed shorter than I remembered but still had that cute/attractive face. Her dark hair was much longer and she had it pulled back into a ponytail. I then thought of Gretchen and wondered what she was up to. When I finished talking my friend asked me if I was going to try and see Gretchen. I hadn’t seen her since I graduated high school. I hadn’t been back to my hometown much since college and was working out of state. My friend encouraged me to go.
It was much easier to find Gretchen because she lived in the exact same apartment complex! All I had to do was look her name up in the phone book. I thought about calling but decided to drive over instead. I was actually a bit nervous as I walked up to the second floor and knocked on apartment 2c. I could hear someone coming to the door. When Jenny opened the door I froze for a second. Then introduced myself just in case she had forgotten my name. Jenny smiled and began saying she recognized me from the hospital. We chatted for a fee minutes glossing over what I had been up to and why I was there. Jenny informed me Gretchen was working as a waitress and would be back soon. She invited me in.
I was shocked that the apartment was exactly the same just much more rundown looking. It seemed much smaller than I remembered too. Jenny asked if I wanted anything to drink but I passed. She helped herself to a wine cooler and sat down. Jenny turned off the TV and decided to confront me about the night she saw me naked. Jenny said enthusiastically, “So…I want you to know that I still recall the night I caught you fucking Gretchen.” it was more a statement not a question. I just shook my head and smile sheepishly. I also noticed she said Gretchen and not her daughter which seemed odd. “You left quite an impression on both of us.” I gave her a questioning look as to what she meant. Jenny smirked, “You have quite a nice piece of equipment down there.” she pointed with her middle finger at my crotch while holding the wine cooler in the same hand. I even looked down some what amused that she was so bold to say it. Jenny shifted her short thick legs on the couch. “You really did a number on Gretchen. You were all she talked about after you two broke up.” I had to interject that Gretchen had cheated on me and that was why I broke up with her. Gretchen knew she had messed up and tried to get back with me. We did have sex a few times but I couldn’t get past who she cheated on me with. Plus, I had no intentions of ever really getting back with her and used her for my self gratification. We both said hurtful things but our last talk was just before leaving for college and that conversation was quite civil before saying good bye. Jenny went on stating, “Gretchen never got over you.Did you know she thought you two were going to get married?” I had no clue she thought that way nor did I ever bring marriage up. Then the mood got somber for a few moments when Jenny explained what Gretchen had been through during my time away. Gretchen, for a better word, became kind of a slut. She slept around, according to Jenny, but nothing lasted. The guys she hooked up with were not the greatest and her experiences were not good either. I began to think coming there was a mistake and told Jenny I should just go.
I stood up but Jenny popped up off the couch and blocked me spilling over the little that was left of her wine cooler. She touched my arm and quivered while she stroked it. I got a funny feeling and my cock was beginning to grow. Jenny looked up at me. She looked cute when she smiled and the glasses she wore were a turn on for me. “You know that I have thought about you for a loooonngg time too.” Jenny brushed up against me. My mind told me this was seriously fucked up but my cock was saying ‘Let’s fuck this bitch!!’
My cock won…
We kissed and moved quickly into her bedroom. It was animalistic!! I ripped off Jenny’s clothes quickly. She was pale, chubby, and curvy all over. We got naked and I wasted no time mounting myself between her legs on the bed. We rubbed our naked bodies up against each other as she sucked on my earlobe and I squeezed her fleshy breasts with my hand. She reached down and I guided me into her. Jenny let out the sexiest moan as my inches moved deeper inside her. She felt moist and warm. Her pussy made juicy sounds from my strokes in and out of her. Jenny moaned sexy, she talked dirty, and she played with her tits! The trifecta was insane. She let me suck on her nips and the harder I pounded the more she loved it. I was really into it and wondered why I didn’t fuck Gretchen’s mom sooner. We fucked missionary, doggie style and cowgirl. Everything was intense. Our bodies were sweating and I wanted more. We stood up and I took her from behind as she leaned over into a chair. I groped her breasts as our flesh smacked into each other. Jenny moaned like a pornstar, she begged me to go harder. So I did. He chubby flesh rippled from the pounding. Then out of left field we heard……”What the fuck!!!!!”
We both looked over and there was Gretchen standing in the doorway wearing her waitress outfit, open mouthed. I stared at her but kept pounding my long hard extra thick cock into her mom. I was so close, I couldn’t stop myself. Jenny kept her head down and moaned for me to cum. When I ejaculated my seeds deep into Jenny, I was looking at Gretchen. She had aged, she looked tired, she still had skinny legs and arms but her belly looked huge and disproportionate to her slender frame. She had never developed those small tits of hers. My body convulsed into Jenny multiple time as I deposited load after load of my semen into her. When I finished, I pulled out still somewhat hard out of Jenny’s soaked pussy. Jenny stood up wearily and let put a pussy fart, expelling some of my goo down her legs. She slipped away to the bathroom. The door was missing so Gretchen and I were forced to listen to Jenny fart and sputter cum out. Gretchen just looked at me. I saw anger, hate but also hurt. She turned away and bolted for her room.
I was conflicted for a moment and almost went after Gretchen but Jenny had come up behind me hugging me and playing with my cock. It felt really good and I turned around. I pushed Jenny down on me and let her suck me dry. I heard Gretchen storm back but I couldn’t move as Jenny was like a vacuum going down on me furiously. She looked up at me and impressed me how well she swallowed my cock down her throat. Gretchen now even more mortified swore at her mom. She came over and pushed her down. Jenny had accidentally bit down on me as she fell back. It didn’t draw blood but there was a couple of teeth marks. Gretchen went after her mom. I grabbed Gretchen up off the ground and held her. It probably wasn’t the brightest idea because she slammed her fist back into my cock and I let her go as I buckled. Gretchen then kicked her mom as Jenny tried to fight back. The yelling was so loud and the way Gretchen berated her mom was alarming. I stepped in again. I grabbed Gretchen, picked her up and threw he down face first onto the bed. I laid on top of her pinning her hands down. She flailed her legs and I had to use my legs to hold them open and down on the bed. Gretchen screamed! Her behavior was not helping me as I was naked on top of her and was getting turned on in a sadistic way. Jenny had blood coming from a cut on her lip. It was puffing up already and she grabbed her side where Gretchen had kicked her. She took deep breaths and winced in pain. I figured she had a broken rib. Jenny put her top on and slipped her jean shorts up gingerly. We exchanged looks and she said in a almost nonchalant way, “I need a moment” and limped out of the room.
Gretchen saw the shape of her mom and stopped shouting and fighting me. I told her I would let her go if she would agree to calm down. My adrenalin was pumping and my cock was still semi hard. I moved off of her slowly making sure she didn’t make any sudden moves. I unpinned her arms and moved off. I then stood up and dressed quickly just pulling my jeans up and carefully zipping with no underwear. Gretchen turned over and sat up on the bed. I begged her not to go after her mom. She just sat there with an empty stare at me. Then she began to cry. She buried her head into her hands. I put my shirt and shoes on quickly and kicked my underwear and socks near the bedroom door. I thought I should leave but Gretchen was a wreck. So I did the dumb thing and sat down next to her on the bed. I put my arm around her and she collapsed into me. Gretchen sobbed and sobbed. She cried out that it should of been her over and over. I didn’t know what to say so I just held her silently. After what seemed like the longest thirty minutes of my life, Jenny returned. Her cheek looked puffy and she was icing her face. She moved in and I released Gretchen but she clung to me. I softly said, I should go and Jenny helped me pry Gretchen away. She sat down taking my place and I grabbed my underwear and socks and left.
Do I regret fucking Jenny? No way, the sex was amazing.
Do I regret being caught by Gretchen? No, while it did pull on some heart strings, she got was she deserved for cheating on me.
Am I an asshole? Yep!
Did I hook up with Jenny or Gretchen? Well, wouldn’t that be a fun story…. Lol
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