Let me first say that I wasn’t the most popular guy in High School. I was a

normal looking guy that dated normal looking girls. I did learn that as the

girls grew they became more and more desirable but at the same time I became

more and more in awe of them

I always knew I was somewhat different. Most guys most wanted to just fuck as

many girls as they could. Get a quick orgasm and get out of there. I instead

loved the smell of a girl’s vagina. I enjoyed giving pleasure to a girl with my

finger or my mouth especially. Most girls at first thought this was “not right”

somehow but after I started I usually got them to an orgasm. Once they had that

first orgasm it was OK to do that again right or not. Some wanted to save

themselves for marriage. That was also OK with me as long as I could bring them

to an orgasm orally. Some girls wanted to return the favor by masturbating me

or a few with a half hearted blow job. Most girls were OK but I knew I wanted

something more. I was in awe of a great pair of legs connected to a wet vagina

or an ass behind a wet vagina. Anyway here is the story of my first experience

with an older (wiser) woman and FemDom.

I was in High School and the school was off for a week so I took my old

clunker up to visit Marty, a family friend in Worcester, Massachusetts. I had

visited him many times with my parents and he had just started out on his own.

He had a small apartment in the old section of town and kept up two jobs to

support his lavish (not hardly) lifestyle. When I visited earlier with my

parents he had a morning job delivering papers and I used to go with him early

in the morning to help out. His main job now was at a metal factory but he had

kept his early paper route job. He had been at both jobs since he graduated

High School about a year and a half ago and the two jobs were taking its toll.

The first morning I helped like I used to and that night he said would I

possibly take the route the rest of the week and he would pay me so he could

sleep in for a week. I agreed as I like to get up early in the morning. The

first day we delivered the papers together, I really didn’t see anyone as most

people were asleep. Marty delivered the papers on the last house on the last

street (High St) and told me to turn his car around so we could get back to his

apartment. Marty said to deliver the papers in a certain order such that I

always finished on High street and I agreed. That first day it took quite a

while to get all the papers delivered. The houses on the last street (High

Street) were old wooden three and four story apartment buildings. The last

house on the street was four stories and I was glad to see it because I knew I

was done and could get back to Marty’s apartment for a snooze. When I got to

the last house on High Street I delivered the papers to the front door porch

from the bottom to the top. When I finished at the top apartment the owner met

me at the door and said I should deliver the paper to the back door only. As

this was the last house I thought OK and walked down the four stories and up the

back four stories. As I got to the back door, the resident met me again at the

back door. This door was unlike the front door where I could only see the

resident’s face but rather a full screen door where I realized that the resident

was a shapely older woman (probably in her 30’s). She invited me into her

kitchen to have a drink by saying “Why don’t you come in for a drink? Marty

always does.” I obliged as I was done delivering the papers. She brought me a

coke with ice and had me sit at the kitchen table. She was quite beautiful and I

felt a stirring in my shorts. She asked me who I was and why I was substituting

for Marty. We had a great conversation and little by little I realized she was

naked under her fluffy robe. She had the biggest tits I had ever seen and was

wearing spike high heels. This further turned me on as I have a “thing” for

spike high heels. I had some experience with High School girls and knew what a

young girl wanted but she was very sophisticated. I got up to leave and she

walked me to the screen door. I somehow felt very comfortable with her. As she

walked to the door with me she let the robe fall open and I saw she was wearing

a blue push up bra and matching blue thong panties. She seemed to ooze

sexuality and every step she made on the kitchen floor caused a sharp click from

her high heels. I couldn't take my eyes off of her and she noticed. At the

back door she asked me how long I was in town and I mumbled an answer as I felt

her hand slide down the length of my thigh. She wasted no time sliding her hand

between my legs to feel my fully aroused cock. She asked if I liked what I saw

and I said yes, very much. She then said softly into my ear “Come back tomorrow

with no underpants. I hate underpants.”. She squeezed the tip of my dick,

turned and closed the door.

I returned to Marty’s house and caught him just as he was getting ready for his

factory job. I asked him about the lady on High street and he said that her

name was Naomi and that was part of the reason he kept his paper route. He told

me she was a little kinky but he always had fun and I should just take it as it

comes.

I couldn’t wait until the next morning. I delivered the papers extra quick and

finally got to 101 High Street. As I finished delivering the papers Naomi was

waiting for me at the back door in a pushup bra skimpy panties and high heels.

She opened the door and asked me into the house and I had to brush up against

her as I entered. She led me into the living room as I watched her walk in her

skimpy outfit and heels. My dick was hard as a rock and straining at my jeans.

Naomi watched me follow her into the living room, walked up slowly to me and

gently slid her hand up and down my thigh, teasing me. As soon as I felt her

touch, I felt a tingling in my dick and more straining at the jeans. She

expertly slid her hand down to my pants button and quickly had my jeans open

revealing my rock hard flag pole. She wrapped her long fingers around my ridgid

cock and led me into her bedroom. Her hands were soft and finished in beautiful

long red fingernails. She left me standing in the center of the room as she sat

on the bed crossing her long legs. Naomi just sat on the edge of the bed her

eyes trained on my erect cock with a devilish smile I will never forget across

her lips. She told me to strip and that's exactly what I did. Her eyes seemed

to cut right through me as I dropped each article of clothing to the floor. I

felt awkward but somehow comfortable standing there, completely naked, with her

eyes focused on me and my aroused cock. I didn't want to disappoint her so I

just stood there totally naked, trying not to look at her face but looking at

her fantastic body. “You will do.” Was all she said and she stood up and walked

to me. She slid her long index fingernail under my cock pausing at the tip to

wipe the precum off my dickhead. She stuck out her tongue seductively and

cleaned the precum off her nail. She then slid her fingernail under my chin and

said “ You will call me Mistress Naomi and will speak only when spoken to.

Don’t move!” She quickly turned and left me naked in the middle of the bedroom.

I could hear her in the in the bathroom, but I didn't dare move or say a word.

In what seemed like twenty five minutes but was probably only two she reappeared

to find me standing exactly as she left me. Naomi however was completely

different. She had on a black push up bra and black thigh high stockings held

by a black garter belt and was holding a black riding crop. When I saw her I

felt my cock shudder again. She commanded me to my knees slapping the riding

crop to her thigh. I quickly complied as she sat in a chair at the other end of

the room. She seemed so powerful and in control. She curled that index finger

to me and I crawled to her. She commanded me to kiss her feet and I quickly

responded. As I finished the first foot she spread her legs and commanded “Eat

me!” I quickly moved up her leg to her snatch and started sucking on her

clitoris; which most HS girls responded quickly to. She stepped on my erect

cock with her foot and said “Slow down Stud. Let’s enjoy the process. You will

make me cum only when I want to.” I had never heard a woman speak like that and

my cock seem to stiffen even more. I slowly brought her to a series of moaning

climaxes. She controlled my movements by putting both hands on my head and a

high heel tip under my balls. It was like she was playing a musical instrument

she directed me in my movements to give her maximum satisfaction.

After Mistress Naomi was finally satisfied she got up and moved to the bed. She

sat seductively down and again motioned me to her with her riding crop. “Let’s

see what you got, Stud. You will only cum when I say so! Do you understand?”

I was hard as a rock dripping precum at that point and ready for anything.

She laid back on a large bed pillow and spread her legs over the end of the bed.

She again curled her finger for me to come forward. I stood in front of her my

dick straining to get in that perfect pussy. Mistress Naomi said “You have been

good so you can fuck me now.” I immediately knew what was expected and started

to pump her pussy over and over until she was squealing with delight. I had

drained my cock myself last night (masturbated) and before I started the paper

route so I could hold out quite long but Mistress Naomi seemed to want more and

more. She used her pussy muscles to milk my cock for all it was worth. I

finally felt a swelling in my balls and as I was about to let go. Mistress

Namomi must have known and grabbed my balls and squeezed until the feeling

passed. Although it was quite painful during her squeezing it felt great again

when I started pumping again. This continued on for what seemed like hours and

I was drenched in sweat. I kept pumping and pumping with Mistress Naomi

controlling my dick until she said “Fill me you young stud”. I pumped her hard

after that and within seconds I pumped my cum over and over into her wet vagina.

My body jerked back at each stream of cum shooting into her. It was like

nothing I experienced before. I had never held back that long before and was

surprised to find my erection was reduced but by no means gone. I continued

pumping and pumping the sweat dripping off my forehead onto her gorgeous tits.

Mistress Naomi just laid back and enjoyed my pumping moaning every so often.

Even though I was fully drained I felt I was somehow fulfilling a need Mistress

Namoi had. Finally Mistress Naomi had enough and commanded me to “clean her

up”. I pulled out my still erect cock and knelt between her fabulous legs to

suck her dry. The salty taste of my own cum mixed with hers turned me on in a

kinky type of way. Mistress Naomi drew me up from between her knees and forced

me to stand in front of her. All she said was “Stand still!” She took my acing

cock into her mouth and sucked me dry. She really knew what she was doing. I

quickly felt my balls swell up to unload again. Mistress Naomi grabbed my ass

and held me while she sucked every drop down her throat. After the first oral

ejaculation she teased my balls with her nails and sucked me to fullness again.

I never had had so much attention given to my cock and it seemed to respond on

it’s own. This time it seemed to take forever to get me to the brink of cumming

but Mistress Namoi was patient and worked me over the brink. I know I didn’t

cum as much as the first few times but she had an evil smile on her face as I

finally went limp. She cuddled me into her breasts and caressed my wet hair.

We later took a shower together and fucked one doggy style in the shower before

she told me to leave. It was late afternoon when I returned to Marty’s

apartment and fell into a deep sleep.

Marty woke me after he returned from his factory job and I told him all the

details. Marty said Naomi had called him at work and that they both should be

there tonight for a special treat. We ate a big dinner at Denny’s, took showers

and we both got dressed for the evening (without underpants) as Naomi

instructed. Marty said you should masturbate before you leave because it will

help. I was amazed that I still had some cum left but did as I was told.

Marty and I walked to 101 High Street and Marty explained that Naomi was married

but had a special relationship with her husband. Most mornings Marty would

service her before work but sometimes she would have Marty over in the evening

and have her husband watch. This was to be one of those times and Marty told me

not to worry. We both climbed the stairs and waited on the back porch for

Naomi.

Naomi opened the back door and led both of us into her kitchen. Naomi was

dressed in a short tight black miniskirt, shinny red top and silver spike heels

with lacing up her calves. This immediately got my dick straining to get out of

my jeans. An older man (30s) was standing by the sink doing the dishes in a tee

shirt, shorts and an apron (her husband I thought) She handed us each a cold

beer in a frosted mug and took a mixed drink for herself from the counter as the

three of us sat at the kitchen table making small talk. Marty took a sip of his

beer and then stood up and started kissing Namoi’s neck as she drank her drink.

I just watched and sipped my beer trying to get comfortable with my dick

straining to get out. Finally, Naomi got up and commanded both of us to open

our pants. Marty quickly unbuttoned his jeans and zipped down the zipper. I

did the same. She walked over to us and grabbed a rigid cock in each hand and

led us to the living room saying “Arnold, clean up the kitchen and then you can

watch.” She led through the living room to the second bedroom (obviously

Arnold’s). In the room were kinky toys, a table, a pad in the corner (for

Arnold to sleep) and a large round red chair/bed. Naomi sat on the chair and

commanded us to strip which we both did quickly. She said, “Arnold, get in here

and clean up!”. Arnold entered this time without the apron with his head down

and quickly picked up our cloths, folded them neatly in two piles and sat on a

small stool in the corner of the room. Naomi stood up and removed her top

seductively over her head letting her big tits tumble out and settle high on her

chest. They were perky, tanned and magnificent. She dropped the red top onto

the floor and slowly removed her miniskirt stepping out of the pile on the

floor. She was tan from head to foot, no tan lines, except a small triangle on

the top of her ass. She kept her heels on and picked up the riding crop. She

slapped the crop onto her thigh and commanded Arnold to clean up her cloths.

Arnold moved quickly to pick up her cloths folding and putting in a third pile.

Arnold’s shorts were so short they looked like women’s hot pants and Arnold’s

penis end was sticking out of the bottom of the shorts. Naomi walked

seductively to the mirror on the wall and snapped her fingers. Arnold quickly

obtained a brush and clip to put her hair up into a bun. Obviously Mistress

Naomi was the head of the household. Finally she seemed to remember we were

standing there naked and erect. She again grabbed both of our cocks and

positioned us to her liking. She said, “Arnold keep quiet and you can watch a

set of young studs satisfying your Mistress.” At that she commanded me to sit

on the round chair and proceeded to lower her cunt onto my rock hard cock while

sucking Marty’s cock into her mouth. I was in ecstasy her tight cunt working my

cock like a baker kneads a loaf of bread. As I was really drained earlier in

the day and I masturbated before we left so my cock was ready but not willing.

Mistress Naomi seemed to know this and worked herself over my rigid rod such

that I was a human dildo for her pleasure. I looked over at Arnold and he was

watching intently all the action but did not move from his seat. The next thing

I heard was Marty saying “Mistress, I have to cum.” Mistress Naomi said “Boys

cum at will”. Wherein Marty jerked his head back and unloaded into her mouth.

Mistress Naomi removed Marty’s dick from her mouth and let the ropes of cum fly

onto her neck and breasts. She left Marty to sit on the bed and started

concentrating on me as I finally felt my balls tense for action. Mistress Naomi

removed herself from me and squeezed my balls and said “Stand and cum inside me

stud”. Naomi pushed Marty on the bed, bent over the bed and started licking

Marty’s dick to fullness presenting me with her magnificent ass and I started

humping her doggie style. I slid my cock in and out holding her tiny waist for

balance. Soon I felt my balls swell up ready to go. Again Mistress Naomi seem

to sense this and moved her ass in reaction to my pumping, milking me to the

climax. I felt her tense as I was about to cum and she slid her ass down fully

onto my dick. I erupted over and over into her hot cunt. By this time Marty

was ready for more and we reversed places. Marty standing doggie style with

Mistress Naomi sucking me to hardness again. After Marty unloaded a second time

Mistress Naomi positioned herself between both of us and teased my cock while

brining Marty to full hardness again. She then pushed Marty back down on the

bed and started to suck his dick. Mistress Namoi stopped for a second, turned

and commanded me to “Fuck me up the ass Stud”. I complied as best I could and

found her anus lubricated but very tight. I didn’t last very long because I had

never done this before and she used her ass muscles to milk my cock. I exploded

with another climax deep inside her ass. All the while she was milking Marty’s

cock. Namoi just couldn’t get enough. Finally we were both limp and in

Mistress Naomi’s words, “Useless to me.” She called over Arnold who quickly

cleaned up the cum on her neck, breasts, vagina and ass using only his tongue.

Mistress Naomi commanded “Arnold, get the boys some more beer”. Arnold quickly

finished up his cleanup chores and brought us both a cold beer along with a

mixed drink for his Mistress. We sat content on the large chair drinking our

drinks trying to regenerate. I was the first to bounce back and Mistress Naomi

noticed my inflating cock and said, “Looks like round two”. She quickly put

down her drink and sucked my cock fully into her mouth. She was an expert.

While giving me that blow job she caressed my balls and ass with her finished

nails. This attention to my cock and ass was too much for me and I quickly

unloaded again into her hot mouth. She continued giving blow jobs to Marty and

I as she used her free hand to massage the other’s dick to fullness. I never

thought I could cum this many times and after awhile I felt thirsty again.

Marty had more endurance than me and at some point I had to watch the action

along with Arnold. Finally, Mistress Naomi drained both Marty and I so much

that we both couldn’t get it up again. Again, she had Arnold clean her up and

get us a snack and drinks. I really thought I would never get it up again and

Marty later told me that this was one of the best sessions he had ever had with

Naomi.

Finally Naomi decided we were through and commanded Arnold to “bring the boys

their cloths” which he did quickly. We both started to dress and Mistress Naomi

said “Do you boys want a chance to watch?”. Marty said “Yes Mistress”.

Naomi snapped the riding crop up and quickly got Arnold naked and strapped to a

table by his bed. She put what looked like a handball attached to a strap into

Arnold’s mouth and connected a chain by clips from his nipples to his ballsacks.

Namoi then used the chain to pull his balls and nipples painfully away from his

body. Arnold quickly began to sweat and groan. This torture continued for about

20 minutes and I found myself getting aroused again beneath my jeans. Mistress

Naomi observed this and brought me over to where Arnold’s head was turned,

unzipped my pants and sucked me to a final dry cum in front of poor Arnold.

Mistress Naomi returned to Arnold and said “You have been a good slave today and

you know that your Mistress needs young studs to satisfy her. Not a puny little

dick like this.” With that she opened a drawer pulled out a strap on dildo and

fucked Arnold up the ass. Arnold erupted all over his stomach just as Mistress

Naomi thrust the last of 10 strokes. That was too kinky for me and I zipped up

and motioned Marty to leave.

I had the greatest sleep I ever had and the next morning woke up early to get

back to delivering papers. I was the personal entertainer of Naomi for the rest

of the week. On the last morning I was there Namoi gave me a deep long kiss

goodbye. I will always remember that kiss. I sometime wonder where Mistress

Naomi is now; Probably satisfying herself with Arnold watching.