I confess, these are my personal conquests.
This will be an ongoing post of most of the girls I have been with, ones I have gotten pictures from and the new ones as they happen. I've posted on ML before with a separate post for each girl, this will be a cumulative collection.
I will call myself DDDP.
Lets start with.... hmmmmm... We will call her "B"
B was a young girl... I literally met her off of wouldyouhitthis.com. She was a fucking freak... I dated her for 2 years (while I was dating other girls of course, but don't tell her that). This girl was an aspiring alternative model.... and a huge fucking slut. She sent me dirty pictures and movies nearly on a daily basis. Looking at all of the media I saved from her its nearly 3 gigs. I actually sold this stuff on auction sites a few years back so some of you might have something from her but its unlikely.
This was the first girl I ever taught to squirt and holy fuck was it delicious. She loved anal and even played with her dog for me. I could've married her if she wasn't a bi polar manic depressant skitzo bitch.... well and I was dating another girl for over 6 years when I started this "relationship" with her. Give me some feedback and I will continue with the stories and different girls.

** Caution Gay sex ahead **

Quick Story Details:
I'm 38 Married 6'2" 212lbs fit, dabbled with some Bi stuff as a teenager, never did anything more than mustal hand jobs
Guy in question, My neighbors Son, 20 5'7" 150lbs? Trainer at a gym and is in incredible shape, 100% Gay

My wife is away on Girls weekend to Atlantic City, I just got back from a business trip. Neighbors Son, Jeremy is watching our dog. I come home a little earlier than expected about 9PM, and can't wait to hit my Jacuzzi after a long travel day. I come in, drop off my suitcases in the laundry room, strip down and stroll on out to the deck to the Jacuzzi where I see Jeremy hanging out with one of my beers in his hand!

We were both shocked. I just stood there naked like wtf and he tosses the beer and acts all embarrassed. I finally speak first and say...wth man, that's alcohol abuse, stay there. I go to he fridge grab 2 beers and come back and hand him one and tell him he's earned it for watching the dog. I then get in the Jacuzzi with him,

He's quiet for awhile and I'm just sighing, and relaxing, and he finally speaks up..."I hope you don't mind that I'm here, I thought you might be pissed!" I said, "No not at all, me Casa su Casa" It's then I noticed his clothes were on the chair next to the patio table. so I said..."Naked too huh?" He says, "yeah, I let Lucy out and it looked inviting, so I stripped down and came in" I said, don't worry about it, Baths are made to be Naked. You don't shower with a bathing suit on do ya?" he laughed..

We chatted more for about an hour each getting out here and there to piss and get more beers, but I won't bore you with that BS..

We get to talking about sex lives, and he's wondering how I handle long business trips with no sex, and I say, well I look forward to coming home and getting a BJ from the wife and fucking until the sun come's up, but unfortunately, she's not home, so I have to wait another day!"

He says, too bad you're not gay, because I've been staring at your cock all night, and I'd be happy to give you a BJ right now if you asked me!!

I admit I was little uncomfortable for about 3seconds, and then I lifted myself up to the end of the tub and sat down and told him....go for it...

He launched himself across the tub so fast that wave of water came up over the side along with him, as he hungrily sucked my cock, which was already hard, right into his mouth.

I never got a BJ from a guy before....he knew what to do!!

He was sucking, and stroking, and moaning, cupping my balls, kneeding them, taking me deep into the back of his throat, swallowing as much of me as he could fit. (proud 9.25") I told him I was going to cum soon....and he stops sucking me and squeezes my cock tight, looks up at me and says NOT YET!

He gets up goes to his clothes and back-pack and gets what looked like hand lotion. I could see his hard cock bouncing as he moved back and forth. he comes back and says, "I know that Maria (wife) doesn't like you to fuck her ass, (which is true, she'll do it, but she's not a fan at all!!) so now is your chance to fuck an ass HARD!!"

He gets back in the tub and bends over the side, takes the lotion and covers his asshole with it. I get behind him and press my hard cock against his hole, He says, Let Me, and he holds my cock steady in his hand as he rocks his ass back and forth on me getting it in ...working that hole open. I'm watching as my head presses in and out and in and out. He finally presses back more and my head pops all the way in...He let's out a "ohhhhh Goddd" and continues to press into me. (Holy shit was it tight!) He moves back right up to my balls, so slowly, and keeps saying, Fuckkk Fuckkkkk omg fuckkkk. He tells me not to move and I just stand there as we stand connected. He finally starts to move a little, and then a little more, eventually he's taking me out to my head and back down to the balls,,,slow at first but now faster. I'm just watching my huge cock disappear in that hole. He finally says...NOW, Do it now...fuck me Hard as you can!!!

Without hesitation I grabbed his hips and slammed into him. he started moaning so loud that he grabbed the towel we were using to dry off and stuffed it in his mouth to muffle his moans. I could feel my balls building but kept trying to hold back, wanting it to last longer. (Football Baseball, ice dancing, Naked Rosanne Barr, anything!!) I fucked him HARD for what seemed like a good 10minutes. I could feel him jerking his cock under us. I finally said.....I'm going to cum...He muffled,,,,CUMMM IN MEEE. I was cumming before he even got the last word out.....I pushed my cock as deep as I could get it and filled his ass with cum.

I stood there for while, expecting my erection to subside, but I was still rock hard, like I took a Viagra or something. Jeremy started to push back on me, I thought maybe he was trying to push me out, but instead I reached under him, and pulled him back to me and sat down back inside the Jacuzzi with me in his ass on my lap... I reached around and stroked his hard cock underwater.

He just said, fuckkk yes and started to grind his ass on my cock as I jerked him. I kept alternating hands, right hand, then left, then both...He'd bounce on my cock and then grind, and twist and make circular motions...I was still hard and I could feel cum building again. I jerked him faster and faster, he started convulsing and grinding on me faster...the waves in the tub were starting to be a problem...but finally he says....Fuckkkkk I'm cumming....and I could feel the cum pulse through his cock in my grip. With each pulse he'd thrust his hips upward and his ass would grip my cock and pull it so hard that I came in his ass for a 2nd time no more than 5seconds after he finished cumming.

This time, my cock subsided almost instantly and it worked its way out of his ass, along with a river of cum.

We both immediately got out of the tub and dried off, both out of breath and not saying a word. I finally said...Looks like I'll have to drain the tub. He said, well I'll come by to help if you need it.

I said, sure, but please know that this is our little secret, He assured me, that mums the word, and added..."Btw, have you ever had a cock in your ass?" I said, No, I just don't see me doing that, I may have to just draw the line at receiving a BJ and being the top to your bottom (with a laugh) " He said he'd be OK with that, and he left.

The following night my wife was home and we fucked until the sun came up per usual, but I have to admit....when I talked her into anal, I couldn't help but notice that Jeremy's ass seemed tighter than hers! I could just chalk it up to different lube, or her ass being used to my cock, but it was an odd realization. But once she took the toy in her pussy for some DP, that ass tightened up like a drum and I came HARD!

I admit that I want to fuck Jeremy again. I might even try a cock in my ass. Not sure. But definitely not in my mouth. I still prefer the taste of pussy vs cock!

Trained to become a black, group, sex slave

A few years back I spent time on and off with several
shall we say more dominating types of gentlemen. One of
them, who for this I shall call Leroy, just loved
when we got together to make me totally helpless.
It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo
and when he found out i was free that weekend he insisted
on coming over later that afternoon.
We talked about when and what he wanted me to be
wearing when he arrived. We settled on 4:00 and I was
to be wearing a red waspie, black fully fashioned nylon stockings,
black bra, short tight black skirt, red long sleeved
button up satin blouse and 5 inch black heels. It was about
noon time so I have plenty of time to make myself
ready.

Leroy arrived right on time as always. I greeted him
at the door with a hug and kiss and he returned the
favour. We went into the living room where I had a nice
bottle of white wine and a cheese and cracker plate on
the coffee table. We sit on the couch together, drank
some wine and talked some before finally he started to
caress my leg and press into me to kiss me. It was
like old high school days making on only now I was on
the receiving end and loving it. It got kind of hot,
me laying back on the couch, Leroy on top of me
kissing me, my legs entangled in his, it was
wonderful.

Eventually he started to unbutton my blouse and pulled
it off, he pushed me to my feet and pulled off my
skirt then pulled me back down on top of him where we
continued our kissing only now he was nibbling on my
ears and kissing my nick. I was so turned on and hot.

I was so worked up and started to work my way down his body
to give him what I know every man really wants…as I
reached his belt with my kisses he held my shoulders
tight and said "wait"….he then pushed me up and had
me stand up. He then said he would be right back and
went out to his car. I waited a minute or so before he
returned with a bag. He took my hands and said if we were
going to do this we would do it right.

He then pulled out several ropes form the bag
and went about binding my wrists behind my back. He
then undid by bra and removed it, which was strange
because he had never removed it completely before. Then with
another rope he wrapped it around my chest and
forearms pulling tight making sure that the ropes around my
chest went above and below my breast area. Next he
took another rope and worked that behind my back and
around the rope that he had put around my arms and chest. Each
time he would pull it tighter and tighter. This did
two things, it pulled my arms further back and also
pulled the ropes around my chest in so it made my small breasts look larger and
protruded my nipples. It was amazing to watch
that happen and I was kind of loving it. Another
shorter rope he tied to my wrists pulled them up and
wrapped it around the ropes at my forearms and then
took the two ends and draped them over my shoulders
and down to the ropes around my chest where he tied
them off.

Next he pulled out this narrow couch table we used to
put keys on and positioned it in the
middle of the room before me. He had me stand up
really close to it straddling the two legs on the end.
He then went about binding my legs to the legs of the
table. Next, he tied a final rope to the ropes he
draped across my shoulders and pulled me forward so I
was laying down on top of the table. He tied off the
rope to the end other end of the table so I could not
rise up.

There I was, totally helpless and at his mercy. The
next thing I know is he is stuffing a ball gag between
my lips and telling me to open wide bitch…once it was
in he buckled it up behind my head.

You can just visualise me, flat on the table, tied and unable to move
and my legs spread wide ,fixed to the legs of the table.
My mouth was gagged and i was already beginning to drool.
At this point he took out his camera phone and took a few
pictures, only 3 or 4 at the most. He then began to make several calls on his cell phone.
As he was making the calls he walked away into the
kitchen where I could not hear his conversation. A few
minutes passed before he came back and pulled up a chair
next to me. He kissed my cheek, slapped my ass and sit
down and went about telling me I was in for a real
treat. In his words, “You wanted to be a slut so I am
going to make you a slut, you are going to become a real Black mens bitch.”

About 20 min later the door bell rang and Leroy went
to answer…I was freaking out now. What had he done and
who could that possibly be….some laughing and hello’s
I heard as footsteps came down the hall towards where
I was. Next thing I know Leroy is introducing me to
three other Black guys and to be honest, I don’t think I ever
was told their names.

At first, they were a bit taken aback that Leroy had a transvestite
like me in captivity. It is very taboo within their culture, to say the least.
They were sensible though and though “what the fuck , a hole is a hole”
lets just stay and see what develops, lets keep an open mind.

They rubbed my butt and ran their hands across my
back. One was talking about me but not to me about what a
sexy a bitch I was and was thanking Leroy for
inviting him over to break in his slut.

At some point I felt the cold lube being squeezed out
onto my ass ring a couple of fingers probing and
spreading inside my ass. One guy yelled "she is gonna become the perfect anal slut!"
Then it started, Leroy was first. I know this because one of the guys said
something like, “She is your find Leroy, you first mate”

I could feel his hard cock press at my rosebud. Then
he leaned hard into me and pushed forward.
I winced a little and he held where he was
for a moment before pushing forward more. A couple
more thrusts and he was all the way in, his big black cock inside my tight ass
and I was breathing heavily and drooling around the ball gag.

Leroy started to pump in and out as the other three
encouraged him on and taunted me by telling me I was
just a fuck hole slave who's purpose in life was to exist only to pleasure Black men
and be used like a street whore. Soon one of them I guess got too
worked up just watching so he freed his hard, black cock from his pants,
unbuckled the ball gag, popped it out of my mouth and replaced it
with his throbbing hard cock. He told me to make sure I did
not bite him or he would beat my ass till I was bloody
red. Needless to say I was very careful. I could not move as he
violently throat fucked me whilst Leroy piston fucked my ass.

Leroy, I could tell, was ready to explode. He went all ridged
and his pumping slowed and he held my hips really tight
and was grunting…well, I was grunting also actually,
the throat fucking was producing tons of spittle which
was only helping to make my mouth more lubricated so the cock
went down further.
Leroy pulled away and then another guy just stepped up
and took his place…just about the time this new guy
got a rhythm going the one in my mouth shot his load.
He was holding my head tight, grabbing me by the hair
and yelling at me to "swallow bitch, don’t lose a drop, today you are going to be filled with Black cum."
He came and then withdrew from my mouth and I found standing there, in his place, Leroy.
Leroy said, "my cock has been up your ass, clean it cunt”…so I
took him into my mouth and cleaned his cock. Soon Leroy was cumming down my throat
as the other guy in my ass was losing it and
making his own deposit. He slowed then stopped and
then backed out and flopped down in a chair. Next, the
fourth guy entered me, he was bigger than the other
three, i am glad that he had waited until last, as he
really stretched my hole. He was so excited by the
previous action that he came within just a few thrusts.

They all seemed to be really satisfied. Leroy slapped my ass
and thanked me for a good fuck and suck and they all
collapsed on the couch and switched on the TV.
It was a Saturday and now about 7:00 or so. They
put on a football game, replaced the ball gag in my mouth and where sat around
chilling and enjoying the game. They'd helped themselves to beers and were
talking as I lay there all bound and
helpless with cum all over my nose and chin.
They were talking about this crazy shit about using a tgirl and came
to the conclusion that whilst their wives and girlfriends were not
giving them all the sex they needed , that this sexy , compliant tgirl
would be a very good alternative to use on a regular basis. After all ,
she had a hot mouth and ass was tighter than pussy, right!

I was kind of dozing when Leroy touched my shoulder
and offered me a drink of water which I welcomed. He
smiled at me and patted my head telling me I was a
good girl and he knew I would be even a better girl by
morning. He then stood up, undid his pants and flopped
out his cock for me and ordered me to kiss it….I
did. I was untied from the table and taken to the bedroom
and secured to the bed corners. At the same time the other three guys came in and
one said “Round Two, I am first this time” and before
long, there I was, getting fucked in my ass and
sucking off Leroy. They would switch up. At one point, I was untied and
the guy with the largest cock sat on the edge of the bed
Leroy picked me up and dropped me on to his cock.
Then Leroy pulled my legs up high, leaned me in to the other guy and then placed his cock at the entrance to my ass.
"Take a deep breath and try to relax slut", said Leroy.
Before i knew it, Leroy was using pressure and was gliding in to my ass as well.
I now had 2 cock in my ass.
One of the other guys stood on the bed , so my face was at his crotch level,
grabbed my hair and started to face fuck me. I now had 2 big black cocks inside me,
2 in my ass, 1 in my mouth. The fourth guy started taking pictures with his camera phone.

When they had all cum, i was retied, gagged and left there until around 2:00am when Leroy
untied me. By then they had used me as a fuck toy four
or five times.

When I got untied Leroy had just let them out to go
home. Leroy got me a drink and some
crackers. It took about a half hour or so before I was
able to really stand and walk on my own.
Leroy kissed me deeply and told me
I was the best bitch he ever spent an
evening with and asked me if i wanted to carry on living the role of Black mens slut.
I said "yes".

To be honest, I don’t even remember him leaving me
that night. All I know is that I slept tell past noon
that day and was pretty darn sore the rest of the
weekend.

Leroy's three friends spread the word around the gym,
to all the local guys about me, showed them the pictures, telling them that i was a loose, hot bitch. Again , to begin with they couldn’t quite get their head around
the notion of using a transvestite like me. After seeing the pictures though
very soon, dozens of guys were almost knocking down Leroy's door
asking him if they could use his bitch.

Leroy put a plan into action. EVERY Saturday or Sunday,
whenever there was a match on cable television, i was to make sure
that i was at home, dressed like a slut and that my apartment
had a good stock of beers. I was to open the door and welcome any man
inside who wanted to come in. Every weekend, i had between 6 and a dozen
black men in my apartment to watch the game. Naturally, the game was
just a diversion, as i was to stay in my bedroom, lubed and ready to
service any guy who cared to come in.
My place soon became known as THE place to go. Married guys could tell
their wives that they were going to the pub, to meet up with their
mates, to watch the football in the bar on the big screen.
All the time, they were coming to my apartment and using me like
a whore. My life was complete!

Make my fantasy come true? Make me that sex slave ?
[email protected]
Can travel to be chained and used.

This is me a few years ago with my clitty locked, my ass plugged, in slutty lingerie, waiting for a gorgeous young black girl i met online to come over. She said she was into dominating and owning a sissy slave boy and would be taking the keys to my cage with her and would use my desperation to cum to make me into anything she wanted me to be.

I was dressed in a black, lace teddy, fishnet thigh high stockings, a modest pair of black heels and most importantly, a big black butt plug, trapping a few ounces of cumlube in my boypussy. I had given myself an enema and restricted my diet, so my hole was extra squeaky clean.

As soon as she came inside, she took one look at me and said "good, here, take these." and handed me 3 pills. I recognized the bar of xanax and what looked like viagra, but Before i could ask about the other one, she grabbed my wrist, pulled me into my room and shoved my onto my bed, face down. I swallled the pills, and figured I'd taken much more than that before.

"Dont fucking move." She had already noticed the cuffs at the corners of my bed and restrained my wrists and ankles. She reached under my caged clitty from behind and gave it a yank, so she could see it from the back, between my legs, and thats when she noticed my plugged ass.

She gave it a few solid smacks, and asked, "How long have you had this in your pussy?" As I opened my mouth to tell her, she grabbed the base and yanked it out of my asshole, which was incredibly painful, enough to make me scream a humiliating, girly squeal. I heard her laughing behind me... I was genuinely in so much pain, I had tears running down my face, and i could feel my hole convulsing, stretched wide open, with warm cumlube pouring out. She assured me that the pain would be temporary, and said something about being addicted to her big black cock. I was only able to mumble, "mmmhmmm."

She stripped down to her panties at the side of the bed, and teased me while I watched her rub oil all over her smooth, perfect, chocolatey skin. The scent was intoxicating, and soon I forgot about the pain in my boypussy, and tried to reach my strapped down arm out to her. I cought the waistband of her Thong, and as she backed up, her panties came down her hips a bit. She chided me and told me boys like me dont deserve pussy.

I whined, and continued to stare desperately at her beautiful glistening body, perfect round tits, proportional with an ass that id let suffocate me... legs that lead right up to a lean, panty clad groin..... my clitty was throbbing uncontrollably. She then stepped onto the bed, straddled my gaping, lubed up asshole, and said, "Pussy boy sissies like you will never get pussy again, not now, not ever. Do you understand?"

I nodded, and wiggled my ass to her, and she said, "From now on, you belong to Big Black COCK," and after a few suspiciously warm and fleshy feeling smaks around my cheeks and hole, I could feel the pills kicking in... I felt like a cock hungry whore willing to do just about anything to get off. I could feel myself slipping into a sedated, obedient, slutty mindset, and my whole body felt like it was glowing, with a soft, warm, buzz. My mind was escaping me, leaving my body to be nothing but a fuckhole sex toy for the woman on top of me, teasing my ass with her fingers and pouring copious amounts of slimy stringy lube directly into the gaping boyhole.

Then i felt a few more teasing, fleshy smacks against my hole. With what little coherence i had left I remember saying in my head, "thats one realistic dildo... mmm" and i could imagine a throbbing, girthy, veiny BBC, breeding my cunt like a real girl, trained only to cum from being fucked, serving only black cock, for the rest of my life.

Without warning, she shoved the entirety of apparently, her 11" Big Black DICK—NOT a Strapon, Not a dildo—SHE WAS A TRANS WOMAN. I had never been with a guy, and was never turned on by men or boys, and it was making me so horny and confused that I liked this... a lot.

That was her DICK tapping against my ass. A REAL PENIS. Unlike my useless caged nub, she was endowed by the Gods, and I could FEEL IT. I actually liked it... I mean, its gotta be better than a dildo, right? Why use cold, hard rubbery plastic when you can have the real deal? Well, this was the realest fucking deal I have ever made. She got to know me as a woman, and had all the aspects and traits of a beautiful, sexy, charismatic black woman, but she had a dick... And she was having her way with my helpless, intoxicated, submissive body, raping my wet, hungry fuckhole with her long, thick COCK.....

And I was in heaven, I could feel the sensation of tingling buzzing warmth, head to toe, and felt her giant BBC directly penetrating almost a foot inside me, while every inch of her massive Dick made full contact with my P-spot every single stroke.

She wasted no time, and was already fucking me at full speed, pounding my lube-filled, sloppy, gaping wet boypussy, with her grabbing me by the back of my neck, forcing my face into the bed and spanking me repeatedly. She called me all the degrading, derogatory, humiliating names ive ever heard, and then some. I felt like my entire existence was about to change forever, as she dangled the keys to my cage in front of my eyes, and told me my useless clitty is never going to be used again, and that had better learn how to have anal orgasms because that's the only way sissy slaves cum.

The viagra made my clitty strain against my cage, and i could feel a distinct stream of cummies pouring out of the tip, with more and more every thrust. The sedating effects of whatever else she gave me caused me not to notice i was moaning and saying, "yes...... yess...... fuck me........mmm"
I felt her change angles and alternated between slow, forceful thrusting, to deep, rapid short strokes of her giant cock, and I felt a strange feeling in my clitty and boyhole at the same time.

It grew into a feeling like I had to go to the bathroom, and I panicked, but I knew I didnt have to, and had just had the enema.... then it turned into a throbbing, pulsing sensation inside my ass, right behind the base of my clitty.... She was fucking my asshole relentlessly, and the sounds of her meat penetrating my pussy were like a trance. She noticed my throbbing boycunt, tensing up and spasming, "Ohhhhh who's a good gurl? Are you gonna cum, babygirl? Hmmm? You gonna cum like a slut for mommy's BBC? If you do, you're never going back to normal. You got that, bitch?"

I was too overstimulated to reply, and suddenly the sensation exploded within my inner asshole, sending waves of orgasmic ecstasy to every inch of my body. I had tunnel vision, and all the sounds around me morphed into one continuous, godlike aural sound, while i was left helplessly convulsing with my arms and legs strapped down, and i could feel a non-stop burst of cum being shot out of my clitty, squirting all over my bed and pooling between my legs, as I gave in to the single most intense and surreal full body anal orgasm, which seemed to go on, and on, and on, and on...

To this day, i have no idea if it was 60 seconds, or 60 minutes. I came so uncontrollably with a Trans Woman's BBC literally fucking the cum out of me while my mind melted, sedated and rolling on some Molly-like drug at the same time, while being forcibly aroused by viagra, making my clittly feel so tight and confined, throbbing and spurting cummies all over from within its cage, while the keys dangled from her neck, and she reminded me of the fact that I'd be chasing this experience for the rest of my life, and that she and her BBC were my only hope, and my primary goal in all of life, and wouldn't have it any other way!

CONFESSION:

A long time ago, but not too long that I can’t remember it, I had an affair with one of my step-mothers. I don’t know which number she was, as my father never told us about some of his wives, but I do believe she had been wife number four and number seven at different times.

She had waited for the right moment to begin in earnest. There wasn’t much but “accidentally” left open doors and some “oops” nudity during the first marriage. Enough to make me curious but not enough to be inviting to trying something.

During the second marriage is when things went full blown. By this time my father was not able to have sex at all because of medication he was taking that left him impotent. When he was away she’d play and play often. It wasn’t odd that she’d have a couple male (and some female) friends over for the weekend, all of them holed up in her room, while the stench and sounds of sex came from within.

The years between marriages hadn’t been the best to her. She was never quite hot to begin with but she had some looks. During the first marriage she was skinny with small tits and what could be considered a bigger ass for her frame. When the second marriage came around she had been doing drugs and living hard for awhile and had acquired a bit of a paunch. Her ass didn’t look as good with the paunch, and her small tits were not nearly as firm as they had been before. Like I said, not quite hot but had some looks that she’d let go a bit due to drugs and hard living. Still enough to get my young hormones going though and if you hadn’t seen her from before there wouldn’t have been enough of a difference for anyone to care.

My father was out traveling the country as part of his job for weeks on end. It ended up with just her and I in the house most of the time and she kept up with the “accidental” door openings, more overt teasing than before (she loved parading around the house in nothing but a towel that just barely covered her). I fully admit to standing at a vantage point to see through the door while her and her friends were inside, jerking off to her getting fucked. I was still at the point where I wasn’t sure if she knew or not; sometimes I was sure she knew but other times I doubted it. She never really let on either way until after we started fucking.

I’m also pretty sure she had spied on me when I was jerking off in my bedroom alone. I’d hear a floor creak or a rush of air would jiggle the door (we had really shitty doors) just enough to know someone had been outside of it a moment before. I know she had watched some of my first ever blowjob.

She had a liberal view of friends coming over, which meant that I could have girls come over to spend the night just as much as guys. I’d fooled around some with girlfriends but never really closed a deal on anything until a girl I knew came over to spend the night. Her and I weren’t a couple and were barely friends at the time but it was one of those “we know this is going somewhere, we just don’t know where…” type relationships. Early the next morning, after a smoke or two, the girl and I got to talking and I negotiated a blowjob from her. I sat on the bed, she pulled my cock out, and sucked it like a pro. As this girl was sucking me off I saw something out of the corner of my eye, in the window, a shadow or something, that moved. I looked over and saw something dart down. I caught just enough of the black hair to recognize that it was my step-mother’s head that had gone out of sight. I told the girl that I wanted to change position. I stripped naked, we changed position, and she went back to sucking my cock. I played with her tits and looked out the corner of my eye at the window. I had positioned us so that if my step-mother were to look again she’d get a perfect view of everything; my cock, the girl sucking it, the girl’s tits… everything. After a minute or two more the girl was set to make me cum and I got a bit loud. I saw that movement at the window again and did a quick glance; it was definitely my step-mother and she was watching the climax. I came in the girl’s mouth, at the girl’s insistence, and made sure she got every drop. I stood up and the head disappeared from view again.

Nothing was said until later that night when after dinner, while my step-mother and I were sitting on the couch in the den, she asked if I had gotten any from the girl. Even though I knew she knew I still had that bit of doubt that crept in, just like when I was outside her door jerking off, and I told her that I had gotten a blowjob but not revealing that I knew she had watched.

This was another thing she was liberal about: sex talk. She’d ask questions as if she were doing a paper for some sex studies class but without being clinical about it. She’d go downright raunchy when she wanted. She asked if it was my first blowjob, how it felt, did I cum in her mouth or on her tits or on her face, did I fuck her, did she rim me or finger fuck my ass… just about anything one could ask.

So I told her about it. Told her it was my first, it felt great, came in the girl’s mouth and how I was bummed she had to leave instead of being able to stay and get/do more. As I told her all of this I was getting hard again, thinking about the blowjob, and the fact that my step-mother was in that damned towel wasn’t helping matters. I didn’t realize at first but she was getting closer to me on the couch as I was telling her. Around the time I got to the part about being bummed that I wasn’t going to get anymore for awhile she was almost on top of me, which is when I noticed. I noticed that she was so close to me that I could feel her tits, small as they were, brushing against my arm. I swear I could feel heat from her pussy emanating onto my thigh. I looked over at her and saw that that damned towel was undone just enough so that I could see down it at her tits. The hard-on that I had got harder, which surprised me, and I knew there was no hiding it as the bulge on the front of my pants was just too noticeable.

As I stared at her tits, finally silent, I felt her hand move onto my bulge. She was alternating between light and hard strokes over it, driving me crazy. She caught my attention and I looked up at her face. She confessed that she had watched through the window and it turned her on to see me getting my first blowjob. While she confessed this she undid my pants and put her hand into my underwear, stroking and squeezing my cock. I sat there staring at her face, relief and shock vying for control of my mind as at least one secret was out in the open.

She then pulled my pants and underwear down and off, straddled me, and played with my cock, jerking it. She told me that she knew I’d been jerking off outside her bedroom door, that it turned her on to know I was watching her get fucked. As she told me this she moved the head of my cock to rub the outside of her pussy. She moved in and kissed me, full on tongue. When she pulled back she discarded that damned towel then whispered into my ear, “You don’t have to wait too long have some more…”

The last word had barely enough time to linger in my ear as she grabbed my cock and put it inside of her. She used her hands to push me back onto the couch, kissing me as she took the rest of me inside of her. She was riding hard but slow, deliberate strokes, showing me a good time while also getting herself off. After the initial shock of what was happening wore off I got into it and kissed back with the same passion she showed. As she was getting closer to climax she started riding faster and harder, letting out moans. I could feel my own climax building and told her so. She told me to cum inside of her and as I did she grasped me tight, shivering. As I emptied the last of what I had she fell into me and panted, shivering more. I asked if she was alright and she responded yes, but that I wasn’t done. She “may have cum once but once isn't enough”.

We lay there on the couch for a bit, had a smoke, then she took me to her bedroom. She lay down on the bed, spread her legs and told me to eat her. I was apprehensive, as I had never done so, but knowing that she’d guide me. I kneeled down and started licking her. She tasted quite good and I didn’t even care that I could taste myself and my cum in her. All mixed together it tasted great. I took her directions as I ate my first creampie and soon enough she was cumming. She made me go one more time, this time adding in eating her ass, and she came once more all while directing me to how she liked it.

When I stood up I was hard again. She pushed me onto my back on the bed and started sucking my cock. After a minute or two she stopped and asked if she was better than the girl from before. I told her it was no contest. She retorted, “You should bring that girl back and I’ll teach her how to really suck a cock” before returning to doing so herself. I was getting close to cumming again when she stopped.

After wiping her face off she came up, kissed me again, and said it was time for me to fuck her right. She moved onto all fours and told me to fuck her from behind. I moved up behind her, trying to get my cock in, when she reached behind and guided me. Her pussy felt like an even better heaven from this angle and I started pounding away as soon as I got a groove going.

A couple minutes later I was cumming inside of her again, deeper this time. When I had finished I popped right down to eat her again. It had tasted so good mixed together before I wanted more. I had better access to her pussy and ass this time with a far grander idea of what she liked and ate her like she enjoyed. She came once more and we took a bit of a long break.

After resting, making small talk and having a few smokes she said me she was going to be direct with me. She told me she had wanted to fuck me for a long time but held off until I had done something with someone else first. She said she was trying to wait until I lost my virginity but couldn’t and settled for the blowjob I had gotten. She had hoped that I’d take advantage of the two of us being home alone all the time, what with my jerking off to her getting fucked, but got frustrated that I never worked up the nerve to do something.

Then she gave me a choice; we could make this a one time thing and be done with it or we could continue. She told me that if we continued she’d make sure I’d experience things most people would spend their lives regretting not doing or trying to attain. She countered that it might be best if I did seek those things out myself in my own time. She admitted that she wanted to keep fucking and to show me the wide world of sex.

I didn’t hesitate to tell her that I’d love to keep fucking her and I’d be more than willing to do whatever she had in mind.

Over the next four years, the length of time that her marriage to my father lasted from that point on, we fucked almost daily. She was or had introduced me to my first everything. She was my first anal, my first facial, my first fisting, my first golden showers and my first pegging. She introduced me to cocksucking and getting fucked by men.

That girl that had given me my first blowjob? She was part of my first threesome with the step-mother, after a little liquor to loosen her up to the idea of fucking my step-mother as well as myself. The step-mother taught her how to eat pussy just like she had taught me. She showed the girl how great getting her pussy ate was. She also taught her how to give a superior blowjob, just like she had said she would.

Threesomes, foursomes, and more. Just about everything under the sun she was a part of the first of.

And the seconds, and the thirds, and the fourths, and…