Do I Or Dont I

For as long as I can remember, I have always loved the sight of women in nylons. All through school there were those teachers, that 25 years later, I can still remember their specific outfits. Miss B in her purple jumper with white nylons. She used to sit on a desk in front of the class and pull up her stockings. Miss C who always seem to get a run in her nylons and she would have one of us boys place a piece of tape over the run. Miss W, short lady, nice breasts, always wore nylons even with jeans. Ah the memories.

So now in my early forties, I still can't go out with being on the lookout for women in nylons. Unfortunately, the ladies here in NB, tend to go barelegged. It is almost a rare sighting nowadays. I have noticed on the internet that women from the UK tend to still wear nylons often.

The other part of this fetish is that I have a thing for older women that I have yet to act on. Fantasizing is great, but I feel time is running out. Hence the question DO I OR DON'T I?

There is this one lady at work that is a tremendous flirt. I often wonder if I should/could take it to another level with her. She is not gorgeous, just plain decent looking lady. She is the type that talks often about sex but I often wonder if she is just all talk? I have run different scenarios in my head and almost think that the best scenario is to lay it all on the line. Ask to see her after work and tell her up front about my fantasy and tell her that I want her to fulfill it. Remind her how long she has been married and that both of are in a similar situation.

We would meet for drinks. She is dressed in a skirt and blouse. Coffee/dk brown colored, seamed nylons with heels. A little make up. During dinner we flirt as she rubs her leg against mine. I rub my hand up her leg to the top of her stockings and caress the inside of her leg. I feel the heat from between her legs. She can help but softly moan. You see, she is 54 years old and frequently complains about how small her husband is and how long it has been since they have had sex. We pay the bill and head to the room.

As we close the door, I spin her around and drop to my knees. I start at her ankles and work my way up her legs. I rub my face on her legs. I slowly lift her dress and to my surprise, she is not wearing any panties, just a garter. I get so hard. I bury my head into her crotch and inhale the sweet scent of her wetness. She moans as she pushes the back of my head into her. Her legs part and my fingers slide into her slit. She shudders as she parts her legs even further. I use my fingers to open her up and run my tongue from the bottom of her hole to the top of her clit as I suck her clit in at the same time. I continue to tongue her pussy as her knees get weaker and weaker and her climax builds. I start to lick her pussy faster and faster, trying to keep up with her moans and intensity. I insert 2 fingers and start to finger fuck her. Her nails dig into my scalp as she tries not to scream out in ectasy. She loses it and cums hard. I leave my head buried in her crotch as I rub her legs. She pushes me away, guilt I assume. I get up and walk up from behind and wrap my arms around her and kiss her neck as I tell her that that was the sexiest thing that I had ever experienced.

From underneath her blouse, I rub her sides, I feel her starting to relax. Then I feel it. She has reached behind to rub my cock. I am about to burst. I don't want to rush her but damn, I want her. I twirl her around and smile. She looks up, our eyes meet and we kiss for the first time. I am having the hardest time staying in control of myself. I want this women like no one else ever before. I unbutton her blouse, red bra. ah marone. I pull the blouse off of her shoulders as I kiss them. I pull down the zipper down on the back of her skirt. The skirt falls down and she steps out of it. There she is, in a red bra and garter with these dark brown stockings. I am taken back. I need to sit. She smiles with confidence. She knows this is right.

While I sit and try to take this all in. She walks closer and sits on my lap. I go right for her stockings. As we kiss, I can't close my eyes, I need to see her. I need to see the stockings, her hips, her small belly and her breast. I need to see her shoulders, her neck and her face. My hands and fingers are all over her trying to absorb every part of this.I don't want to forget a thing.

She slides to her knees and unbuttons my Levis. My cock is rock hard. She frees it and smiles. I get the impression that she is not 100 per cent sure what to do. She wraps her hand around my cock and leans in. A light lick at first and then she takes it all. I want to scream, I grab her hair and pull her off me and lean in for a deep kiss. I finally release her and she goes back down. For years, I had fantasized about this and now I find myself not trying to think about her at all. I don't want to cum just yet. I have to concentrate on not cumming and at the same time, I have been wanting this for years. She works her head up and down. She softly moans as she is tasting me and I noticed that her hand is now between her own legs. She is pleasuring us both. She looks up at me and smiles. I was wrong, she 100 per cent knows how to suck cock. She squeezes my balls and I let her know that I am going to cum, so that she can decide where I cum. She takes more of me in as I explode in her mouth. I continue to run my fingers through her hair as she looks at me and continues to smile.

She goes to the bathroom to clean up and give me a few minutes to recoup. She walks out still wearing the stockings and heels. She sits on the bed and I make my way over. I lay back against the headboard and have her straddle me. I want to see her. She sits across my legs and gently plays with my cock to get me ready. As I start to get hard she pulls her pussy closer so that she can rub my cock against her pussy and get us both worked up. She is beautiful.Her nipples are poking against her bra. I reach up and pull the bra strap off of her shoulder and pull her bra down off of one breast. I squeeze her nipple, she squeezes my cock tighter. Both of us breathe quicker and moan loader. She slides on to my cock, I buck upwards. I watch her hips rock back and forth as she fucks me. I watch her throw her head back in pleasure. She digs her nails into my chest. I move my thumb to her clit. I rub her into an orgasm as she reaches behind and rubs my balls, I start to lost it. I am no longer in control. It was the most intense orgasm ever. I could feel it building at the tip but not releasing. Then she loosens her grip and I flood her pussy with my juices.

We sit and talk. I caress her body. She admits that she has not been with any other man that her husband since she was 18. She says that she was about to back out but like I had reasoned to her, it was a one time thing. We owed it to ourselves to be selfish this once. It was the safer way to go about it this way, as we were not looking for anything from each other but a wonderful sex filled experience. We both had lots to lose, but we both had dreams. Time passes and we continue on with the evening...

Now more than ever, I wonder, Do I or don't I?

Thanks for taking the time to read my first story. Hope it wasn't too long and boring.