Overheard

It was senior year at Redhill High School and spring was in the air. Everybody seemed to be making out on the lawns, amongst the trees and flowers, couples were snogging and frolicking everywhere, perhaps the pollen didn't affect them.

I wasn't with a girl. I was a shy science nerd, allergic to pollen, graduating a year early and an unhappy virgin. I was supposed to be tutoring two jocks from the baseball team that fateful afternoon that set me on the path to losing my virginity 15 months later. They never turned up, so I went home. For some reason (teenage despair?) I decided to have a nap on the couch in my father's study. I fell asleep immediately and woke up to voices from the kitchen next door. It was my mother talking to one of her friends. I would have turned around and gone back to sleep, but I heard that her friend (I couldn't tell who it was) was crying. Intrigued I listened a bit more carefully and then a lot more carefully. It wasn't easy my mom's friend was a mess, she was blubbering, blowing her nose and fairly incoherent. Fortunately, I got the gist of her story.

Her husband (I didn't get his name -that might have helped me identify the woman) had erectile disfunction - even with Viagra he couldn't get a hard-on. And this is where it gets interesting, my mother's friend (I will just call her XX from now on (XX = female chromosome...geeky I know...don't judge me)) said that she had always been horny, but that during menopause her sex drive just went through the roof. Her husband tried to satisfy XX, but sex toys, fingers and oral sex just didn't cut it, XX needed a cock. She needed a hard cock in her cunt (her words, not mine), in her mouth and in her ass. Jesus, I couldn't believe what I was hearing, who was this woman. Did I know her? I couldn't hear what my mother was saying, she was using her soft soothing voice. She must have been shocked.

XX blew her nose and cried some more before continuing her tail of woe. My virgin cock was massively excited to discover that there were real world horny women - that they weren't just internet creations - and that one of them was in the kitchen next door. My cock is and was a normal well-functioning 6.5 inch uncircumcised cock. It was begging for action. If only my mom's friend knew that I was available and more than willing. I took my cock out of my trousers and held it in my hand while I listened to the drama taking place next door. It was vibrating in anticipation of hearing more.

"I have been so desperate for cock I even responded to men on online hook-up sites and met them in a sleazy hotel. I tried three times and I will never do that again they were all fakes, no one was anything like their profile, they were nice to me until we fucked and then they treated me like shit. I left feeling ugly and fat." And with that XX started crying again. Can't say I blamed her. My mom was making some more soothing noises, I couldn't hear what she said but her tone was clearly comforting.

XX wasn't having any of it. She still had more to get off her chest. "I don't know what to do. I love my husband and I am not having some scary fuckers treating me like shit. That is it - I am closing shop, no more cocks in my garden. From now on I will be relying on my trusty dildo, sex toys and of course my butt plug."

I was stunned. I couldn't believe that my mother had a sex starved friend, who used a butt plug. Nor could I believe anyone would want to talk to my mother about their sex life. What could my mother contribute? Who was this?

Mom said something more and then I heard the front door open. I put my throbbing rod back in my pants and rushed to kitchen window to see who the mystery woman was. It was Mrs. Thomas. You could have knocked me over with a wink of an eye. Lauren Thomas and I went to the same pre-K program, kindergarten and elementary school - that is how our mothers met. They also work together in our local hospital. Mrs. Thomas was a big woman - big boned, fleshy but not fat, around 5'10" and 220lbs I would guess. She was a little rough around the edges, but I never got any sexual or sexy vibe from her. In high school I was so horny I mentally undressed every woman I saw and masturbated thinking about them, but I had never thought about Mrs. Thomas in that way. Of course, that all changed in a nanosecond, from that day on Mrs. Thomas was my number one fantasy. She certainly wasn't your typical teenage fantasy material, but after hearing about her desires and needs, she dominated thoughts.

Mrs. Thomas had a large round face, it was rather flat with small blue eyes and a pert nose. She was loud, her mouth was always wet and opened into a very inviting "O" shape. It was only after I overheard her in the kitchen that I realized that her mouth was perfectly designed for blowjobs. How had I not seen that before? It was rare to see Mrs. Thomas dressed up, she liked to dress for comfort, shorts (that did nothing for her figure or big ass) and floppy T-shirts (that hid her tits, I had no idea how big or small they were).

I grabbed my stuff and ran to my bedroom so that my mother wouldn't know I was home and had overheard their conversation. After closing my door, my mother would never come in if the door was closed, I opened my laptop and went to Mrs. Thomas' Facebook page. She was a prolific poster, but didn't post many pictures of herself. I took my cock out of my trousers again and played with myself while looking at photos of Mrs. Thomas. I imagined her playing with her dildo, using her butt plug and crying for my cock. I came three times before I went to dinner.

In the next two weeks I just happened to bump into Mrs. Thomas a few times (you won't believe how much work and planning that took). Each time she acknowledged me, we even had a chat once, but she never saw the real me - she saw her daughter's playschool friend, not the high school senior with an average sized cock that was always hard and was always thinking of her.

There are two reasons why I was still a virgin even though I was a high school senior. The first was that I was a seventeen year old skinny nerd and the second was that I was petrified of rejection and the opposite sex. Three times I called up Mrs. Thomas to offer my services as friend with benefits, but each time she answered I hung up the phone. Driven by raging hormones I gathered all my courage and days before I was due to leave for university I knocked on the Thomas door. I thought I had everything lined up so that no one else was home - wrong - Mr. Thomas answered the door. I stood there so shocked I couldn't say a thing. I wanted to run away. Fortunately (or not) Mrs. Thomas walked up behind him. She was wearing large oversized shorts and a wife-beater vest without a bra. Her pointy nipples were staring right at me. I just gawked at her.

"Are you looking for Lauren?" the object of my desires asked me.

I didn't know what to do and so I just nodded.

"I am sorry, she has gone for the week. She won't be back before you leave." Said the object of my desire, my very own cock starved MILF.

"Okay tell her I said "Bye"." I said and turned around. As I left I could hear Mrs. Thomas tell her husband, "I think the poor boy has a crush on our daughter."

What a disaster now Mrs. Thomas thought I had a crush on her daughter. She had no clue it was her cock-deprived cock body I wanted. It wasn't all bad - at least Mrs. Thomas knew that I was leaving for University and I had seen that she had the most awesome projectile nipples. Another mental movie for my spank bank.

Fast forward a year. Academically my first year at engineering university was a success - my overall GPA was a 4.00 and I enjoyed classes and labs. Romantically and sexually it was a big flat zero; no girl friends, no sex and no lovers. Not many women at engineering school. My hands had never touched a naked boob or pussy. Mrs. Thomas still dominated all my thoughts and desires. She had become my obsession. I used all my computer sleuthing skills to find her on the dating/sex sites. Nothing doing, it looked as if she hadn't gone back to them. Perhaps her year had been like mine, perhaps she had survived by fingering, dildoing and buttplugging herself and perhaps she was as sex-starved and horny as I was, as horny as she was the day I overheard her talking to my mother. I came home with plans and fantasies of bedding Mrs. Thomas. Oh yes, and doing an internship.

I had barely been home for a week, had only seen Mrs. Thomas once, she was visiting my mother (I overheard nothing interesting), when I got very sick with a viral infection. I was delirious and don't remember much. Afterwards I heard that my doctor and mother had contemplated checking me into the hospital until Mrs. Thomas, an ex-nurse turned administrator who could work from home, volunteered to look after me.

Show me a healthy 18 year old virgin (can 18 year old virgins even be healthy?) who isn't preoccupied with sex. A mere fever did not stop my mind, nor my cock from thinking about sex. This feverish viral infection was a truly psychedelic experience for me and it melded reality with fantasy.

I remember arriving in my fluid mechanics class, where I discovered that the class was cancelled because the professor had Covid. My classmates left to socialize and sit outside. My next class, stat-mech, was in the same room so I stayed in the class and did my homework. I was the only one left in the class when Mrs. Thomas came into the class.

"Is this the fluid mechanics class?" she asked. Mrs Thomas was wearing a business suit and high heels.

"Yes"

"Where is everyone else?"

"They left because class is cancelled."

"That is very unfortunate. Prof. asked me to show the class how to use a butt plug. I am sure they would have learnt a lot. Do you want to learn the fluid dynamics of butt-plugging?"

"Yes please. Do you think it will be on the exam?'

"You insulant young man. Are you making fun of me? Not? I am glad to see that." Mrs Thomas took off her skirt. She wasn't wearing any stockings or panties and her thick legs were smoothly shaven and ended in a clean porn pussy.

"Take this butt plug, lube it up and plug me," said Mrs. Thomas as she handed me a 5 inch green fluorescent triple ripple butt plug and a tube of lube. She turned around and presented me with her alabaster white ass. Her ass cheeks were flawless white pillows, invitingly soft with no visible imperfections. Mrs. Thomas rested her chest on the desk and spread her cheeks apart. She was teasing her rosebud with her black fingernails.

"That's enough lubrication. Insertion time." In the front of the empty lecture hall I pushed the anal dildo into Mrs. Thomas' ass. She moaned, swore like a trooper and even claimed that she came. Once the green fluorescent triple ripple butt plug was fully inserted she twerked her substantial booty.

"Look at my ass ripple young man. Do you see the waves emanate from my triple ripple? Now go to the black board and use sinusoidal equations to model my ass's behavior."

"You poor boy. You are hallucinating." There was another Mrs. Thomas, this one was wearing pink floppy shorts, and an over sized white T-shirt. She was in my bedroom leaning over me, pulling my duvet straight and placing her hand on my forehead.

"Wow you are burning up. Have a drink of water. Can't be having you dehydrate." Mrs. Thomas said giving me some water to drink. I had a perfect view down her T-shirt. Mrs Thomas was wearing a tatty old bra and had a comfy tummy - no sign of her scrumptious nipples. As usual she was a bit too loud and too close to me (not that I minded). She fluffed up my pillow and laid me back. Immediately I fell asleep.

Mrs. Thomas v2.1 was more refined than the version in my bedroom, she wasn't as loud, didn't drool, she was wearing a form fitting business suit (the top half at least) not pink shorts and had smooth marble white skin with no visible blemishes. She was sitting on the front row desk, her legs were spread wide open so that I could see her open vagina, I couldn't see the fluorescent triple ripple butt plug, but I knew it was deep in her arse and that was probably why she was wiggling around on the desk.

"Young man, I like the way you think. Those are gorgeous equations, you have exquisitely summed up my arse wiggles." Mrs. Thomas said as she started fingering herself. I was standing at the board watching in awe and hardness.

"Boy, I have shown you my wares. Now it is time to see what you have got. Take off your clothes."

I took off my sneakers, T-shirt, jeans and underwear. It felt good to stand naked in a huge auditorium, showing Mrs. Thomas my rampant hard on.

"Nice cock, bet it would feel good buried deep in my pussy. What's up? Why are you so squirmy? Are you scared of me?"

"No Ma'am. I need to pee."

"Well run. Make sure no one sees you, piss and come right back. I need your cock urgently, I haven't had one for years."

I got up to pee. Felt dizzy and fell down. I was in my bedroom not in the auditorium. Mrs Thomas (the one wearing pink shorts) came rushing over.

"Oh my god! Are you okay?"

"Yes, got up to quickly and felt dizzy."

"Gosh! You are naked. Why?"

"Don't know. I am very hot and need to pee." I said and stood up. I saw the moment Mrs. Andrews saw my very erect penis. Her eyes opened wide, her pupils dilated and her mouth opened to form a beautifully round "O". She was silent. All the blood in my brain rushed to my cock and it was harder than ever before. The excitement was too much for me and in slow motion I crumpled. Fortunately, Mrs. Thomas caught me before I hit the ground. She held me up until I regained my equilibrium. It took a minute until my legs felt steady, Mrs. Thomas was standing dead still holding me, her eyes were glued on my dick and I swear I felt a drop of her saliva land on my arm. She shook herself and walked me to the bathroom.

"What are we going to do with you? I don't think you will be able to point that monster of yours down and pee without making a mess, nor do I think you will be able to sit down and point it into the bowl. Hmm, why don't I open the shower door, we will stand here and you can pee," she said. I was all for it because Mrs. Thomas had taken my erect penis in her hand and was holding it for me.

"Just wait don't start yet," Mrs. Thomas warned me. "I didn't realize that you are uncircumcised. How exciting. Let me pull back your foreskin. Now you can go ahead and pee." I never pulled my foreskin back to pee, but it felt good to have Mrs. Thomas pull it back. I started to piss. Mrs. Thomas stood behind me, her right hand came around me and held my cock, while the left came from the other side and cupped my testicles. As I peed she slowly and gently caressed my cock. When I was done she shook it a few times and pulled my foreskin back and forth a mini slow motion masturbation move. Mrs. Thomas turned me around, reluctantly (I like to think) let go of my dick and walked me back to the bed. I got in under the duvet. Mrs. Thomas tucked me in. I started shivering from the fever.

"Oh you poor boy. I think you may have overexerted yourself. Here let me warm you up," said Mrs. Thomas as she climbed onto the bed and hugged me, laying her leg over my ever erect hardon. It felt so good to have nothing more than a thin duvet between my naked body and my fantasy MILF. I closed my eyes to absorb the feeling of her leg pressing down on my cock. My breathing slowed down and I was in a blissful relaxed slumber, close to sleep, but not quite asleep. Mrs. Thomas gently wiped my brow and gave me a wet kiss on the forehead. She must have thought I was sleeping.

"You really need this sleep, don't you, young man." She said to me, and she was so right.

"Hhmm, what a lovely hard cock you have, so beautiful. You know your naughty Aunty would love to kiss your hard cock. she just loves your long foreskin. Sleep tight now because this Momma is going to the bathroom to scratch her itch." Mrs. Thomas whispered as she got up, lifted the duvet, gave my cock a good squeeze before dropping the duvet down again.

I would have loved to have seen what Mrs. Thomas did in the bathroom and how she scratched her itch, but I was so sick that I fell asleep as soon as she left the room.

Hours later my mother woke me up with some soup and pills. I was wearing my underwear and T-shirt (again?). What was real and what had actually happened? I knew Mrs. Thomas had not guest lectured in the fluid mechanics class, but had she come to look after me, had she taken me for a pee and most importantly had she gone to masturbate after squeezing my cock?

"How are feeling?" my mother asked me.

"Better, but still whoosy and confused."

"Mrs. Thomas said you slept most of the time and had numerous dreams and hallucinations."

"Did she say anything else?"

"No, she was in a hurry to go home. She did say she will come back tomorrow and work from here. We will have to get her a big thank you present when you are better."

Not long after that I finished the soup, had my pills and went back to sleep.

The next morning my mother woke me before she left for work.

"Take your pills after you have had your breakfast and go back to sleep. It will do you good, your temperature is close to normal and your eyes look much more alert than they did last night. Oh yes, I nearly forgot Mrs. Thomas will be here in an hour or two. I have given her the key and she will let herself in. So don't get a fright if you hear someone coming in."

"Thanks Mom. I will see you tonight." I said before starting to eat my breakfast. I must have been on the mend, because I was hungry and ate it all. I took my pills and then before going back to sleep I drank three big glasses of water, took off my underwear and T-shirt and placed them both under my pillow.

Mrs. Thomas couldn't be stealthy if she wanted to and I don't think she had any desire to sneak in. I woke up as soon as she opened the front door, but closed my eyes so that I could observe her behavior and decide whether she had seen and held my cock yesterday or whether it had been part of my feverish dreams. Through squinted eyes I saw Mrs. Thomas come into my bedroom. She saw that I was sleeping, stopped and bent down to take off her shoes - they were high heels. Life was certainly looking good not only was Mrs. Thomas wearing (or not wearing) high heels, she was also wearing a see-through white dress shirt with a lacy bra visible underneath it. Had she dressed up for me? I sure hoped so. She had also applied bright red lipstick.

Under the duvet I was getting harder and harder. Mrs. Thomas sat down in my comfy chair. She was wearing a skirt with a slit. She was a bit too large for her get-up and looked awkwardly slutty, but I was not complaining, in fact I loved the look. Mrs. Thomas' took out her ipad and started reading. Her slit had opened a bit more affording me an excellent view of her thick thigh. I wondered what she was reading. She was getting agitated, crossing, uncrossing and recrossing her legs, sighing and licking her lips. Her skirt had ridden all the way up her thigh which was as large as both my legs combined. I was spellbound and nearly got caught watching Mrs. Thomas, when she got up to go to the bathroom. Fortunately, she was so focused on going to the bathroom she never looked my way and never noticed that I was wide awake. When she closed the door, I looked around and saw that she had left her ipad open. Intrigued I took a look and saw she was reading a Literotica story.

My cock was as hard as a rock, my endorphin levels were on an uptick and I was wide awake. I snuck back into bed to plan my attack. As soon Mrs. Thomas came out of the bathroom I returned to my sleep charade. My heart nearly jumped out of my throat. Mrs. Thomas had her panties and her bra in her hand. She was naked underneath her skirt and her nipples were visible through her shirt. Mrs. Thomas went to her handbag and bent over to put her underwear in the bag. Her big ass was facing me. It was so exciting to know that her arse was naked under her skirt. Would I, could I lose my virginity today? Would I see what was under the skirt.