tagFirst TimeTom Gets Lucky

Tom Gets Lucky


I hope you enjoy this story of a young man getting fucked for the first time. As always vote and comments are always welcome.


I was considered a nerd going through school and was never popular with girls. Actually I was nervous and awkward anytime I was around them. I helped my neighbor with yard work as her husband was older and in a wheel chair. He had a stroke and heart attack. Mom told me she is very lonely and her husband understands she has needs.

I doubt she would have any problem with men wanting her. She was about 5'5 shoulder length ginger hair. Slender body long legs which she showed off with heels. She was always dressed in expensive satin and silk with her hair nails and make up perfectly manicured.

It was her tits that made her noticeable. They defied gravity. She was the same age as my Mom. About 46. Mom's body was well sagging. Mrs. D's stood straight out and jiggled when she walked. Mom says she swears there real and never surgically enhanced. Mom should know. They were college roommates.

I am not too nervous around her because she would never be interested in me. I'm 18 and not a great specimen of male stud. I am 5'10. 120 lbs with pimples and a stutter. She is nice to me offering me water and hot chocolate when I do their yard work and shovel snow. I think it's because she is such good friends with my Mom and is grateful for my help.

The other day I was finishing doing their lawn and putting the lawn mower away. I heard the clicking of her heels on the sidewalk behind me. I turned around and watched her tits jiggle under the sheer low cut white satin blouse and her short skirt swirling showing the top of her stockings.

"I was wondering if you could keep an eye on Mr. D while I go and read to the vets at the VA.? They love love the sound of my voice reading their dirty stories. It's the least I can do after they fought to keep me free." Applying pink lip gloss.

I nodded. Feeling my cock twitch imagining her reading about sex and flashing her body as she shifts to subtly allow them to fantasize. Watching her walk away I wondered if she was wearing full panties or a thong. I quickly went to the washroom to jerk off, which seemed to happen more and more lately. Mr. D was sleeping as I quickly found the washroom and went in. I could smell her perfume and saw her stockings hanging over the shower rod drying.

The scent, the stockings and my visual imagining her reading dirty stories with her tits pressing against her flimsy blouse had my cock spurting hot cum in the air as soon as I pulled it out. Fucking Christ it shot in the air hitting her stockings splattered the wall and still dripping in my shorts, pants and on the floor.

Using toilet paper. I cleaned as best I could. Maybe she won't notice the stain on her stockings. Flushed and walked out trying to look normal.

"What were you doing? Jerking off? You were. Why don't you just fuck her." Mr. D asked.

My face turned red and I shrugged my shoulders. He then explained to me that she has a very high sex drive and since he couldn't satisfy it. He doesn't mind letting her get fucked any where she wants. A young guy like you could probably fuck her all night.

Totally embarrassed and uncomfortable I just hung my head and tried not to piss him off. He went on to tell me that all the deliveries that come here aren't because they need the stuff. Showed me the pantry full of canned goods that they never use.

"I love to see her take cum on those beautiful tits and face though. Sandy used to love it when I would take my cock out of her ass and paint her face." Smiling as he recalled their sex acts.

Just then. Sandy came in and tried to slip by without disturbing us. She came out holding her cum stained stocking. I hung my head and tried to pretend I didn't know about it.

"Tom! I had no idea you were so horny. Would you like me to help you?

I was totally embarrassed but nodded my head. She lifted my head and forced me to look directly in her eyes. Lead me over to the couch. Sat down facing me. Ran her hand up my leg over my hard cock. Undid my pants pulling them down as my cock popped out dripping precum.

She adjusted on the couch. Her tits pressing against her blouse. The buttons looked like they were going to let loose and fly across the room as she inhaled and her nostrils took in the scent of my cum from my jerk off session earlier. My cock twitching in anticipation of getting my first blow job. Looking down her top at her round perfect tits as she looked up at me smiled and took my cock head in her mouth.

I am sweating as I feel her moist mouth tighten on my hard cock as she slides down to the base. I grown as she gently fondles my balls and slides her other hand up her stocking leg raising her skirt exposing her moist satin panty.

She pulled her head back up to my cock head flicked it with her tongue before popping it out. It was too much for my inexperienced cock and I began convulsing as my cock spit out a stream of cum. It hit her chin before she could lock her mouth on it and take the rest of my load in her mouth. Sandy tightened her beautiful full lips under the head of my spewing cock and worked her tongue up and around my shaft.

I clung to her shoulders to stop my legs from crumbling under me. She released my cock. Opened her mouth to show me what I had given her before swallowing. Took my cock squeezing it to get the last drop of my cum and tapped it on stocking clad thigh rubbing it up and down spreading cum to the lace top.

"Isn't much more fun cumming on my stockings when I am wearing them? Now it's your turn to do me."

Sandy sat me down on her leather couch. Slid her top off her shoulders revealing her thin lace bra. Her tits spilling out and nipples visible through the material. I starred wide eyed as she undid it freeing them for me to admire.

Slipped her fingers in the lace band of her satin panties. Slid them down over her small round bottom, down her slender legs over her stockings. Lifting her foot taking them in her hand. Rubbing her clean shaved cunt. Moaning a throaty moan as she stuffed them in and fucked her pantie covered fingers.

I was amazed and totally shocked as she took out her saturated panties with her cum dripping down her leg. Sandra rubbed her panties up her taught stomach over her tits and held them under my nose.

"Follow the scent to the source baby. Then lick it till you fill your mouth with my cum."

I took her tit in my mouth and sucked and bit her nipple hard. So excited to suck on a tit for the first time. She grasped my hair pulled me away hard.

"Easy! It's not a hamburger. Gentle.

Pushed my head back to her other tit. I licked cautiously not wanting to upset her again and massaged the other one pinching her nipple as I sucked the other one. Her head tilted back. I could see her breath quicker as she guided my other hand to her spread legs and wet cunt.

Not wanting to make her mad at me again. I softly touched it. It was smooth and wet as she arched into me and my finger went in. I have never felt anything comparable to the silky smooth feeling of her cunt as it gripped my fingers sliding into my knuckles.

Pushing my head down to her fuck hole and urging me to finger fuck her. I was confused but excited to be experiencing her charms and cunt juice. It was running out into my palm in a honey like texture.

I licked the out side of her cunt lips. Tasting the tart yet sweet sensation of her cunt juice. Mrs. D guided my mouth to her clit and took my hand and fucked herself with it fast and hard. Lapping the fresh juice from her oozing cunt and sucking the mound of her dripping clit. My cock hardened as the sticky nectar filled the palm of my hand and covered my lips and chin.

Suddenly her body went rigid. Then began to shake and vibrate. Her cunt tightened on my fingers as she flailed around as if in a seizure. I pulled back afraid I had given her a stroke as her cunt flowed juice down her legs onto her stockings. I watched her body vibrate and cunt lips twitch. Breathing heavy her tits rising and falling.

Mrs. D took my hand after catching her breath sucked her honey dew from it and motioned for me to come closer. I cautiously approached as she pulled me in and kissed me pitting her cum in my mouth letting some dribble down her chin.

`` Tom I want to feel that big beautiful cock inside me. Can you fuck me with it. Fill my wet cunt with it. Give it to me now.``

Taking my throbbing cock. Rubbing the mushroom head up and down on her clit and wet trembling lips before sliding it in. I pushed slowly as sensation after sensation overtook my body. I knew my cock head was sensitive from jerking it but never had I felt anything so smooth and silky before.

Mrs. D`s cunt seemed to grip and release as my cock slid to the base of my groin. I felt her wet slippery legs around my waist as her heels dug in to my ass cheeks. Using this leverage to grind up and down on my cock.

I pulled out to the head of my cock and plunged in when she lifted up on me and began gyrating and her cunt tightened around me as she moaned beginning to spasm again.

"Fucking Good she screamed. Cum with me Tom. Not in me. Shoot on my dress tits and every where. Make me your cum whore."

I could feel my balls tighten so I obeyed her and my cock spewed just as I pulled it to her quivering clit. My thick cum shot up to her tits landing down her belly on her dress while my cock waved around like a hose spurting cum everywhere.

Instinctively I grabbed it pointed it at her open mouth as my knees began to buckle. I fell forward on her cum drenched tits as my cock rested on her chin oozing cum on her nose and forehead.

Her cum drenched body shaking under me. We both were heaving and grasping for air. I had no idea sex could be so invigorating and exhausting.

"I'm proud of you son. I can't remember when I seen her so fucking hot. Thanks for that. Fuck her anytime."

I had forgotten Mr. D was watching the whole time and I felt ashamed I had committed adultery with my Mom's best friend and the only woman that has ever given me the time of day.

"Now wasn't it more fun cumming on my stockings with me wearing them? I can't wait to show you how to fuck doggy. Maybe tomorrow? Go home and don't tell your Mom about our special help session."

I got dressed. Left and wondered if she was serious about fucking again tomorrow. I am going to google this doggy she mentioned and see if I can find out why she looked like she was having a seizure.

All I know is I'd rather do it with a woman than jerk off.

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