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Stockingtails 01

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Note to the reader** Stockingtails is a series following real events of the writer. Some stories will be 100% true others will have elements of truth. The what ‘ifs’ and ‘could have beens’ of a nylon lover. Hindsight is 20/20** all parties are above the age of 18.


Jessie had known my secret even before we started dating. The dangers of dating a close friend. Either through a truth or dare game, or late night divulge, she learned I have a stockings fetish. Information she used to her advantage. This was how she got me to date her. Most girls I had dated before Jessie were very skinny A cup kind of body type. Jessie wasn’t overweight but she was curvy probably a C cup and had an ass you could grab onto. A short time after breaking up with her boyfriend she started wearing more sun dresses and always paired with some pantyhose. She would always find a good spot so I could look at her legs. I became so caught up in her teasing me, I eventually asked her out in hopes to get my hands on her nylon clad legs.

It didn’t take long. The day I asked her out I was invited to dinner. Her father was the pastor, so it wasn’t a meet the parents’ dinner, more of a welcome to the family kind of ordeal. Jessie answered the door in the same outfit she wore to church that day. A white sundress with yellow flowers. The material stretched snug against her ample breast. She wore tan pantyhose with white tennis shoes. Her mom greeted me and said to sit on the couch while dinner cooked. Jessie sat down next to me kicked off her shoes and placed her feet in my lap. With a smile she asked if I would massage her feet. She playfully wiggled her toes underneath the tan nylons. I reached down a grabbed her left foot. I hadn’t really had much chance to touch nylons and found myself getting rock hard as I did. This didn’t go unnoticed. Jessie’s other foot was right under my cock and now felt its raging state pushing against her arch. Her foot started to rub back as she said, “I can tell you have been longing for this.”

As I rubbed both feet Jessie rewarded me with upskirt shots. Her pantyhose was sheer to the top and underneath she wore satin white panties. Her panties where tight against her pussy leaving little to the imagination of how it looked. The awkward moment came trying to get to the table with no one seeing the tent pitched in my pants.

The following Thursday night at bible study, Jessie found me in the back stairwell as I came in. That day she was wearing a black lose fitting dress and black pantyhose. I knew she wanted to make out before church started.

I reached up behind her neck and pulled her in for a long kiss. As we were kissing my hands began to explore her body. I slid my hands up and down her sides. I moved from her lips to the base of her neck kissing and lightly sucking as not to leave evidence. My hands now ran up and down her back. Lost in the moment I dropped my hands below her waist and now was grabbing both cheeks. I began rubbing her well developed ass in circles, slowly pulling her dress material higher and higher as I worked my way to the goal. Her dressed bunched up above my hands. My hands now free to feel the nylon cover ass. Not wanting to be caught I gave her one last good squeeze and a kiss. As she walked up the stairs ahead of me, she flipped her dress up to show me her ass. She was wearing white bikini cut underwear. I thought one day I wanted to see that view with a thong.

I mentioned before a date night that I enjoyed thigh-highs for easy access. Jessie on the night of the date made a point to let me see her stocking tops. As she sat down in my car, she let her dress ride up. She was wearing a white button up blouse. The buttons pulled tight Kartal escort as the blouse hugged her breasts snugly. A black skirt, which would have been knee length had she not rolled it up. Her black thigh high stockings were finished off with 3-inch black heels. During dinner Jessie had slipped off her shoe and her toes had found my ankle under the table. She had pushed up under my pant leg. She knew she was driving me crazy. The feel of the nylon material sliding against my bare skin gave me an instant hard on.

On the ride home I reached across the car and began rubbing her leg starting at the knee. I slowly worked my way up. Every time I got higher her skirt inched up a more. Once I got to her bare thigh, she was nice enough to hike up her skirt to show her silk white panties. I could tell she would let me go pretty far; In fact she wanted it. As much as I wanted to take full advantage of the situation, it was more exciting to wait. Teasing her just as she teased me with her stockings.

Before dropping her back off at her parent’s house we found a place to park, overlooking the lake. I pushed her up against the trunk, took her by the back of the neck and began to kiss her. As I made out with her, I picked her up and sat her on the trunk. As I pushed into the next kiss, I pushed her legs open. With her straddling me I reached down and grabbed both knees.

I whispered in her ear, “Can I touch it?”

“Yes, please do!”

I moved my hands higher and asked again, “Can I touch it?”

“That’s why I wore the thigh highs! Easy access.”

I inched my hands up higher now, above her stocking tops. “You’re so naughty!”

Before she could respond, I kissed her hard and passionately. All the while moving my hands higher up her thighs. Nearing her special spot I stopped. I winked and told her it was time to go home. This ‘leave off’ teasing continued for the next few dates.

Finally she took matters into her own hands. One Sunday I was in the old balcony running sound, and she came and sat next to me at church. Jessie made it a point to show me she was wearing her black thigh-highs for church. As her father stood in front of us at the pulpit preaching, she kicked off both heels and placed her feet right in my lap.

Through the transparent black her toenails were painted white. She rubbed my dick and thighs with both feet. I noticed she was wearing the black stockings from our date under her dress and a pair of sheer panties that matched. As my dick became rock hard, she reached over and unzipped my pants. Without even having to pull it out, my cock under the pressure sprung free. My eye shot forward looking at her father. My mind raced as her feet found my freed cock. I thought, “He knows! He’s going to suspect!”

Her right foot was now behind my dick as a backstop, the big toe of her left foot was tracing the top of my shaft. The sheer black silky casing rubbing against my hard on felt so good. My heart was a furry, fear of being caught, the joy of fulfilling a fantasy, dread of the aftermath, excitement of the moment, scared someone would walk up the stairs, ecstasy of her stocking feet wrapped around my hard on. My mind was a mess of thoughts. “He’s going to look up here. That feels so damn good. I’ll be found out. I don’t want to stop it!”

She parted her legs to expose her panties black and sheer like the thigh highs. Her pussy lips bare beneath (I couldn’t believe she shaved; my mind was blown). My dick was now stuck between the balls of her feet. Her big toes ran parallel with my shaft as her little toes curled around to take hold of my cock. With her feet in this position her toes stretched out her nylons leaving a sheer gap of Kurtköy Escort material between toes. The stockings gaped off her arch as well, leaving the balls of her feet and meeting back with her foot at the heel. Staring intently at her nylons I noticed they glistened with my precum soaking them.

Jessie slid her feet up and down with ease, my precum making her soles very slippery. As I got close to climax, I grabbed her feet with my hands encasing my dick even more as I push inward causing a tighter grip with her feet. I began rocking my hips forward fucking the soles of her feet. I released load after load that landed on her leg and covered her feet. As quickly as I was done Jessie threw on her heels and left the balcony. I came to my senses and noticed church was done and pastor was praying. Jessie called back up the stairs. “You’re cumming for dinner, right?”

As everyone spoke, shook hands and had coffee, Jessie just walked around with cum soaked stockings. She acted as if nothing happened. I could see the glistening of her instep and legs and wondered if anyone else noticed to.

I showed up after church for dinner and Jessie answered the door. The little minx was still wearing the same stockings, but now you could see the outline of crusty white cum where it had started drying.

“Dinner won’t be ready for a bit. Let’s go shoot some pool.” Jessie said after giving me a hello kiss.

Taking me by the hand she dragged me through the house. As we went down the hallway before the kitchen I reached out with both hands and grabbed her glorious ass. She stepped back letting me get two full hands. I rubbed her ass until a call rang out from around the kitchen entrance.

“Hey you two… You should go into the study and show him the pool table.”

We step into the kitchen where her mom was busy cooking dinner. Jessie’s mom was a milf, and seeing her bent over getting something from below the counter had made my mind wander. Jessie had refocused me, grabbing my hand and pulling me into the other room.

“That’s where we are headed.”

As Jessie started to rack up the balls, I ran my hand up under her skirt flipping it up as I took hold of her lush ass again. Looking down I enjoyed the view of the black string running up her ass crack. She finished racking and called my break. Grabbing my pool stick I walk around the table. Placing the cue down and drawing up my shot, I see behind my target Jessie leaning over the table. I had lost my focus now looking at the v above the table. The cue flew down the table making a lack luster break. Taking a seat behind the cue ball, I waited my turn to distract. She walked around bent over the table and lined up her shot. I reached out grabbing the inside of her knee. I slid my hand to her inner thigh and increased my grip as she sent her cue ball. Two turns and nothing in.

I took an easy shot and purposely missed to hand the play back to her. Before she could bend over to line up, I came up behind her and ran my hands up her loose blouse. I made sure to rub up to the sides of her breasts but didn’t touch them. I rubbed back down to her waist slipping my hands into the skirt’s waistband. Jessie leaned over and sank a striped ball. I sat down and she walked around to sink another. As she tried walking past me to her next play my hand hit the front of her nylon warped thigh. Raising my hand past the stocking top I went all the way up to her waistline making sure not to touch any of the sheer fabric that covered her mound. My right hand found the back of her knee and slid up to find the base of her ass. My fingers tucked into the warmth of her inner thighs but still not touching her panties. I had given Pendik Escort her a tight squeeze before letting her pass.

“Easy access!” She cooed and sunk another ball.

Walking back past me I had access to her other leg. This time repeating the same movements. When my right hand found its target at the top of her skirt, I let my fingers brush over her shaved lips. Her mound covered in sheer fabric felt as wonderful as her legs. She pressed into my touch but pushed past me. As my hands left her body I stood up and followed her. Jessie bent over the table; my hands again rode up her sides under her shirt. This time they didn’t ride up the side of her bra, instead I rode them up under the material. Both hands finding their mark, I took hold of both breasts firmly and began kneading. A moan slipped from her mouth at the same time she took her shot and missed. Jessie lost grip of the pool stick when my index and middle fingers closed down around her nipples. The stick clattered as it hit the table masking the even louder moan.

“You missed sweetheart. My turn.”

Letting go of her, I walked over grabbed my stick (pool stick) and walked over to take my turn. In all honesty, I think it was her turn. I was looking for my next move when she took hers. In the same fashion that she had handled my cock earlier, both silky feet wrapped around my ankle and stroked my bare skin. I focused and took my shot placing the ball in the pocket and the cue ball in the same spot. I wanted the footsie to continue so I took a similar shot putting another ball in a side pocket and the cue ball right in front of me. She had now taken a foot and was running her nylon covered toe up and down my calf. I missed my next shot giving her the table and me my turn.

Without wasting time I sat behind her rubbing her calves. My hands worked up her leg enjoying every inch of her thigh highs. Approaching the prize, my fingers rode up her inner thigh and hit the bottom portion of her lips. Pushing my fingers into her entrance, above her panties, caused her to grind into my fingers.

My other hand found the strip of string and pulled her thong down. Jessie stepped out of her panties while my fingers resumed their position now pushing against her bare pussy. No need for lubrication as my pointer finger slowly worked its way past the folds. Feeling her stretch to accept my finger, I pushed in knuckle deep then out, back in and out several more times. One of her hands gripped the table and the other still held the pool stick.

“Mmmmm,” She moaned as I placed my middle finger at the entrance along with my index finger and continued to push into her. Both fingers went knuckle deep and Jessie started randomly hitting balls with the cue to keep up the pretense of a pool game.

“That feels amazing… mmmm.”

My fingers now fully inside her. I started to pull out to my knuckles and then rammed them back in until my hand pounded her pussy. Her hand left the pool stick and covered her mouth. Muffled moans escaped her grasp as I finger fucked her pussy.

“Mmmmm! Aaahhh! Don’t stop!”

She was starting to get loud enough to get us found out.


She was now meeting my fingers with her own rocking motion, slamming her pussy into my hand as hard and fast as I was finger fucking her. Her hand almost tearing off the side of the table, the other trying its best to stop the string of moans.

“Oh fuck!” escaped from her mouth as her pussy gripped my fingers tight. Spasm after spasm releasing her cum on my hand.

“Everything okay?”

“Yup, sorry, just happy for what I got in the pocket!”

“Dinner is almost ready you two, so finish up in there.”

With that Jessie turned around, sat on the table and placed her feet in my lap. I didn’t take long for her silky soles to bring me to climax. Two loads of cum now drenched her hosiery. I think she enjoyed the excitement of doing dirty things in the open with no one the wiser.

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