Gender: Male Age: 30 Location: Chicago
Based on a true story, some details changed since I promised never to tell.
My sister-in-law, Jess, has always been close with my wife and I. She would spend weekends at our house and join us on family vacations. So when her marriage fell apart and she needed a place to stay we were more than happy to help. Our basement was recently finished and an extra bedroom was waiting for her.
Jess and I have always had a flirty relationship. She is a beautiful woman and at 30 years old was reaching her prime. She is around 5’10 with a full set of D cups and an ass you could bounce a quarter off of. She works out constantly and her blonde hair is never out of place. I have always been attracted to her and looked forward to her moving in.
I work second shift and my wife is a normal 9 to 5 girl, so Jess always had someone around for support. She found a part time job after a few weeks and began saving for her own place. I was enjoying the flirty games and catching a peek of her thong poking out, and did not want her to move out.
I woke up one day around 10 AM and could not get her out of my mind. My cock was hard and I knew it was because of her. I rarely went in the basement out of respect, but with her moving out soon I was feeling risky. I went down stairs and knocked on the basement door. There was no answer so I yelled her name a few times and started down the steps. She is a slob like her sister and had of course trashed my basement. The bed we bought for her was unmade and her clothes were tossed around the room.
I wasn’t quite sure what I was looking for until I saw the top drawer of the nightstand slightly open. I looked inside and my cock instantly hardened. There was a black lacy thong and a small purple vibrator lying inside. I picked up the thong and brought it to my nose. It smelled like the most perfect pussy I had ever eaten and I looked at the dried white spot where her pussy had been rubbing all day long. I ran my tongue over it and imagined how good it would taste right from the source. I shoved the thong in my pocket and examined the vibrator. It was little, but powerful. I ran my fingers over it and could tell she didn’t wash it after her last playtime. I ran my tongue over it and could taste her dried pussy juices. At this point my cock could take no more and I went back to my bedroom.
I grabbed my laptop and lay down on the bed. I started searching for a few good porno scenes and pulled the thong from my pocket. Again, I brought it to my nose as I slowly rubbed my cock. I found a hot solo scene of a young blonde fucking herself with a small dildo. I began fantasying about how Jess fucks herself. If she lays on her back or sticks her perfect ass in the air and fucks her pussy from behind. I was stroking away taking my time and every few moments I would bring her thong back to my nose for another intoxicating hit.
I was so involved in my stroking that I didn’t notice the shadow near the double doors leading into our bedroom. It wasn’t until I heard the hardwood floor creak that I jumped back to reality. I looked at the door and could see someone quickly walking down the hall. I shoved the thong under my pillow and ran into the hallway. My mind was racing about how to explain the thong to my wife. I turned the corner and there was Jess. She was wearing light blue running shorts and a matching sports bra. She was sweating and her usually fair skin was reddened. Her hair was pulled back into a ponytail with just a few strands falling around her beautiful face.
“Oh my god Will, I am so sorry. I just got back from running and came up to take a shower. I saw your door open and wanted to say good morning,” Jess stammered.
She was looking down at the ground between us and I realized that I had run out of the room still fully naked. I reached into the hallway linen closet and pulled out a towel. I wrapped it around my waist and could feel the blood rushing to my face in embarrassment.
“Well…I assume you saw, you know,” I mumbled.
“Yeah, I mean only for a second and I turned away. Please don’t be embarrassed, everyone does it. I don’t want to make a big deal out of this ok. And I think it is sweet that you use Anne’s panties to turn yourself on.”
Just then I realized I could get out of this. I could put her thong back while she is in the shower and she will never know. God knows she won’t tell my wife about any of this. As my mind was racing I could still smell her sweet pussy. But this time it was stronger…more real. I looked down and noticed her right hand was behind her back. Jokingly I grabbed her wrist and pulled her hand around.
“What did you do take a picture of me” I said.
She yelped a “No” as I grabbed her hand with mine. I could feel her index and middle finger were damp. They were slick and warm with smoothness that every man knows when he feels it. She quickly pulled her hand away and her face turned an even brighter shade of red.
“You were fingering yourself watching me!” I had to fake some degree of anger to hide the fact that my cock had instantly grown hard again.
“Ok…. yeah I was. It was hot watching you. And you know what I haven’t seen a real cock in almost a year. I get horny you know, I am not a fucking nun.” She replied. She is just like my wife, acting overly angry to hide embarrassment. I find it just as cute in Jess as my wife at that moment. “Well don’t tell anybody and I won’t tell anybody ok.” She said as she makes eye contact with me for the first time.
I decided this was a make or break moment. She was moving out anyway in a few weeks and she has more to lose than I do. I mean I can always find another wife, but sisters are forever. “Ok fine. Our secret. Now if you will excuse me, I still have to finish. Unlike a woman, a man has to finish once he starts” I taunt.
“Really, you don’t think a woman needs to finish too huh? What do you think I am going to do in the shower smartass” Jess replied.
“Well I am going back to my bed. More comfortable than a shower anyway. Feel free to join if you want,” I said in a joking tone. I turned around and walked back to the bedroom. I left the doors open almost all the way this time. No need to hide what I was going to do. I waited a few moments not knowing what was going to happen next. After a few minutes I still didn’t hear the shower running and I can see the stairs from my bed. Knowing she was still standing in the hallway trying to decide what to do I yelled, “Well are you going to stand there all morning or what?”
Although I was confident, my heart still skipped when she came around the corner. Still in her workout clothes she looked me over, lying there with just the towel still on.
“Ok. Here are the ground rules” she began. “We are just two people who care about each other and both need to get off…badly. We share the bed, we cum, and we never talk about this again for as long as we live. Deal?”
“I’m ok with that if you are” I managed to say without a break in my voice.
She walked slowly to my wife’s side of the bed and lay down. She fluffed up the pillows behind her back and laid her hands across her tight stomach. “Put on something boy/girl, not too hardcore” she said while pointing at the laptop. “I’ll probably just keep my eyes closed anyway”.
I put the laptop between us and found an appropriate scene like she asked. I decided to go first, so I slowly unwrapped the towel. My cock was at half mast and aching for attention. I began slowly massaging my balls while watching the movie. I looked over at Jess and she began running her index finger along the top of her running shorts. With her left hand she began rubbing the underside of her large breasts. I could see her eyes shifting between the movie and my growing cock. When I finally wrapped my right hand around my cock and began slowly stroking it up and down, Jess let out a little moan of excitement.
“Well this really isn’t fair. You can see all of me and I can’t see any of you.” I said.
After a moment of hesitation, Jess lifted her hips off the bed and slid her shorts off. She kept her legs together for a moment until she saw my disappointed look. “Fine. Here ya happy” she said as she spread her legs nice and wide. Her pussy was nicely trimmed considering she wasn’t dating anyone. Her pussy looks almost identical to my wife’s, except her lips are a little thinner. I could see the hair around her slit still damp from earlier and the room began to fill with the sweet aroma of a wet pussy begging for attention. She was more aggressive now. She immediately began running her fingers up and down her slit. With her free hand she was squeezing her left breast hard.
I began stroking faster and harder. My pre-cum was flowing over my hand as I watched her. Neither of us was watching the movie at this point and I closed the laptop. I moved it to the floor and she took advantage of the extra room. She spread her legs wider so that her right knee was now lying on top of my left leg. When her body touched mine, we both shivered. She was rubbing faster now, focusing on her hard clit that had begun to show. With two fingers rubbing circles around her clit, she moved her left hand down and put her index finger just inside her wet hole. She began rocking her finger back and forth as her breathing quickened. My cock was begging to cum, but I wanted to wait for her.
“I can’t hold out much longer,” I panted.
“Mmmm….ok….ok…..just a few more seconds”, she moaned.
Her eyes were open now and looking at my hard, swollen cock. She quickly added another finger to her soaking wet pussy and shoved both fingers deep inside. She began finger fucking herself harder and harder, while continuing to rub her hard clit. I noticed her toes began to curl and she tightened her stomach muscles.
“Ohh…fuck me….oh shit I’m cumming….cum baby cum with me”, she screamed. Her body began to spasm and she held her fingers deep inside her cumming pussy.
“Fuck baby…I’m cumming”, I yelled as I shot load after load of hot cum all over my chest and stomach. I hadn’t cum so hard in years. The cum covered my body as I tried to catch my breath. I looked at Jess and she was staring at my cum covered body, as she lightly ran a finger up and down her pussy and rubbed her stomach softly. We made eye contact and immediately began laughing.
“Here, let me get your towel.” Jess said as she walked around the bed. Instead of handing me the towel, she began to wipe the cum from my body. “Jesus Will. When was the last time you came?” she teased. As she was wiping up my cum, I noticed some ran down my side and onto her hand. As she walked to the closet to put the towel in the laundry basket, I saw her raise her hand to her lips and lick my cum off her hand. She did it quickly and obviously did not want me to see.
We spend the next several minutes laying in bed talking. I was still nude and she didn’t bother putting on her shorts. We were more open than we have ever been. I found out she has never had anal sex, although she does enjoy a finger up her ass during sex. I told her I enjoy the same, however I think she enjoys the taste of cum more than I do.
With that tease she realized I had saw her sampling my cum. She turned red and buried her head in the pillows, laughing.
“Yep, you caught me. I love the taste of cum. And I hadn’t tasted it in a long, long time…so fuck you” she laughed hitting me with a pillow.
I had completely forgotten Jess’s thong under the pillow. I reached for it, but she was quicker.
“Wow, Anne’s got good taste. I have a pair just like these.” For a moment I thought I was in the clear…until she checked the size. She has fuller hips than my wife. “You son of a bitch! These are mine. I wore these yesterday. Where did you get these? What the fuck, how long have you been going through my stuff?”
“Ok Jess listen. I swear to god this was the first time. I never went through your stuff before, ok. It’s just I was really worked up and was curious and I know it was stupid. I am so sorry.
Jess jumped out of bed, holding her stolen underwear. Seeing her nude from the waist down again made my cock begin to stir. She really is beautiful even though she is yelling at me. And even though she is yelling at me, she still isn’t putting on her shorts or storming out.
“I think you are turned on by that.” I yell back.
“What the fuck are you talking about”
“I think you are turned on by the fact that I was smelling your pussy and jerking off…not Anne’s. I know you look at me. So don’t pretend that it doesn’t turn you on. I am sorry about your privacy. I won’t do it again, but don’t play the victim here”.
Jess paused for a few moments and said, “So ok then, maybe it is a little bit of a turn on. But just don’t go in my room again ok.”
“Ok fine, no problem. What can I say, I like the taste of pussy, like you like the taste of cum. So we are even.” I laughed.
Instead of getting dressed and leaving, Jess slid back down on the bed. Her demeanor had changed. Her face was still flushed, but her green eyes were clear. “Oh fuck me, I am going to hell,” she said as she leaned towards my face.
Our lips met softly at first, like teenagers at a park. After just a few moments, she straddled me and lifted me up. We were kissing harder and harder. I slid my tongue between her lips and tasted her sweet mouth. I had fantasized about kissing her for years and now she was in my arms. Her naked pussy was rubbing against my thigh and I could feel her slit getting wet again. I slid off her sports bra and for the first time gazed at her glorious tits. They were full with small pink nipples. I buried my face in between them, smelling the sweat from her run and from her orgasm. I took her left nipple in my mouth and ran my tongue around the edges. She grinded down harder on my leg and began to softly moan. I paid the same attention to her other nipple before she pushed me down onto the bed.
“Ok, here are the new rules,” she panted. “Only oral…no fucking. We have to keep something sacred.”
I quickly nodded and began to push her down my body towards my throbbing cock.
“Nice try…me first” Jess said as she slid up my chest and straddled my face. I ran my tongue down her slit from her hard clit to her asshole. She tasted better than I could have ever imagined. She tasted stronger than my wife, and her cream was thicker, more womanly. I tried to tease her, but she simply wanted to cum again. She began grinding hard on my face as I shoved my tongue into her pussy like a little cock. She was panting as she rocked back and forth. I slapped her ass cheeks and she grabbed the headboard yelling, “Fuck, I love my ass slapped”.
I continued to spank her firm ass and tongue fuck her. She slid down a few inches and her hard clit fell into my mouth. I sucked hard on her pink nub and slid two fingers inside her soaking wet pussy. She immediately began fucking my fingers and I could hear her breathing quicken. I felt her legs begin to shake and I knew she was close. I replaced my fingers with thumb and she began to plead no. Until she felt my fingers slide up her tight asshole.
“Oh my god…how many fingers is that”, she moaned. I slapped her ass twice to let her know. “Put one more…one more please, “ she begged. I quickly worked a third finger up her ass. I had never felt a tighter ass and began to believe she really was an anal virgin. I begin to finger fuck her ass and pussy hard and in only a few seconds she yelled,
“Fuck, fuck, fuck….I’m gonna cum,” she moaned as she grinded down hard on my hand and mouth. She began to shake and I could feel her ass tighten around my fingers as her orgasm ripped through her body.
As she came back down I slowly slid my fingers out of her perfect body and began wiping her juices from my face. She had covered my face and neck with her cum, and bent down to kiss me. We shared a long, hot, hard kiss, before I realized it was finally my turn.
I guess me pushing her head down was enough of a clue and she slid down my body. When her hand first touched my cock, my whole body shook with excitement. She lowered her mouth and slowly wrapped her lips around my hard cock. She ran her tongue over the tip, savoring the pre-cum that had gathered there. While still stroking my cock, she began to work all 7 thick inches into her mouth. When she finally hit bottom we both let out a satisfying moan. Although my wife likes giving head…her sister was a cock-sucking champion. She began twisting her hand while her lips slid up and down my cock. She did not care how wet or messy she was getting…a sign of a true cocksucker. Unfortunately, I could feel my balls tensing up after only a few minutes.
I told her I was close and got off the bed. She knew what I wanted and quickly kneeled before me. I brushed her hair back behind her ears and lightly slapped my cock against her lips. She looked me in the eyes and parted her lips as my cocks slid to the back of her mouth. I grabbed the sides of her head and began lightly fucking her mouth.
All of a sudden I felt her hand between my legs. Her fingers were wet with pussy juice as she began rubbing my asshole. I spread my legs in approval and she slowly slid one finger up my asshole. The feeling was intense and I began to fuck her mouth a little faster. She began moaning around my cock and slid another finger up my ass. The feeling was almost too intense and I said “Ok..no more fingers….mmm….just two ok”. She shook her head no with my cock still in her mouth and slid a third finger up my tight hole. I had never had so much in my ass and my legs began to shake.
She sensed my orgasm and began finger fucking my ass harder and letting me fuck her throat. I felt my orgasm start from my asshole and come through my balls to my cock. I quickly pulled out of her mouth and began jerking.
“Cum in my mouth ok…I want to taste it…please”, she whimpered.
I lowered my cock to her lips just in time. The first load hit her in the back of the throat and her eyes rolled back into her head in pleasure. I placed the rest of my hot cum on her milking tongue, lips, and chin. The orgasm had wiped me out and I fell back onto the bed.
I looked at her kneeling next to the bed and she looked so beautiful with cum on her chin as she slowly swallowed the rest.
“Oh my god, I love you”, was all I could say. Jess laughed and lay next to me on the bed.
“Yeah, yeah…you like getting your cock sucked,” she replied and we kissed for the last time.
This time she did get up and grabbed her clothes. We agreed one more time that we never talk about it again and she ran into the shower. We have both kept the promise till this day and she has even re-married. Although we will often catch the other one looking…wondering what could have been. We remain close, but I don’t think we will ever be that close again.
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