Paid for Pleasure - MILF

The last thing I wanted these three men to think was that this was my first time. I was worried they might have second thoughts of spending so much money on me if they knew just how nervous, hesitant and anxious I really was. I say anxious, but it was really a different kind of feeling that gripped me as he took me by the hand and lead me to the table where the other two were seated.

"Good news, guys. She's accepted our offer. By the way, what's your name, babe?"

"Dee, my name is Dee" I said, trying to convey calmness in my voice as the other guys smiled and introduced themselves.

As we all walked towards the back entrance, Sid was waiting, his huge arms crossed on his chest. Again surprising me, he leant down and whispered in my ear;

"I'll be watching babe. If they do anything you don't like, bite down hard on your bottom lip and I'll be in there before you know it."

"Thanks, Sid" I said, genuinely glad that someone would be looking over me.

As the three men and I walked into one of the rooms in the back area, I thought for a moment. If Sid was able to watch me the whole time to know if I was in need of help, he must also be able to see everything I did with these guys. That made me hotter than I already was. The fact that he would also be watching as I fucked three complete strangers for the first time for money, made my nipples ache with anticipation. Sexual anticipation. This was going to be fun.

In the room, the elder man closed the door, then approached me, handing me another bundle of cash. I played it cool, and counted it. Two thousand. Correct, just as promised. Three grand to spend an afternoon with them.

"I'm Ed. This is James, and he's Troy" he said, introducing the other two. "I promised them I'd take them out for a day they would never forget if they achieved our targets this quarter. So...here we are!"

"Take a seat, boys" I told them, indicating they should all sit on the bed.

In my secretary's outfit, I moved slowly in a dancing motion. I told them to strip as I wiggled and writhed in front of them in the small room. I threw my hair and head around a little for effect as I watched the men undress. Ed was paunchy, as most middle aged men are, but the two young guys were in great shape. James was slim, with a long, lithe body like a runner. Troy, however, was my kind of guy. He had a totally hairless chest, with nice pecs, and a six pack that my hubby Steve used to have!

All three of them played shy, leaving on their underwear. Ed wore jocks, James in some really nice Calvin boxers, and Troy was wearing a small bikini style black pair of undies. Very nice.

Slowly I began to strip. I was wearing the blouse and skirt over my stockings and suspenders, with a thong underwear. Unbuttoning the shirt, I curled my finger to Ed, indicating that he should come and join me in font of the other two as they watched.

Ed stepped in behind me, and his hands found my breasts as I continued to unbutton my blouse. Pulling it free once undone, Ed's hands caressed and squeezed my boobs as they sat encased in my bra. I reached back with my hand and found his cock, now erect, pressing into the palm of my hand. I gave it a squeeze as his teeth found the nape of my neck, and gave me a sexy wet bite!

I threw my head forward, wanting to avoid him leaving a mark. As I did so, he grabbed the shirt and pulled it from my body, leaving me standing in front of the three men in my stockings, suspender belt, bra and heels. I love wearing this older style lingerie, and judging by the erections the three men now had, they did too.

"Get on your knees, baby, and suck my dick in front of these young studs. Show 'em how a man's cock should be worshipped."

His words were firm, but not threatening, and as he had paid me three thousand dollars, I did what I was told. I acted the whore, and was loving every minute of it.

I dropped to my knees, positioning myself to the side so they could see what I was doing as I blew their boss. Ed stood there, hands on hips, in the classic 'having his dick sucked' pose al us women know so well! I moistened his whole shaft, using small sucking and licking motions at first. Then, I forced his penis into my throat until I was able to take all of his dick into my mouth and throat. I'd say he was about seven inches long, because I managed to get it all in without any discomfort.

His hands dropped to my head and gripped my hair, pinning my throat on his dick for a good ten seconds, before he let go and I gasped for breath a little before resuming my blowjob. The sight of his boss forcing his dick into my throat must have been too much for Troy, because suddenly I felt hands on my boobs as I was on my knees. My bra was removed, and the hands were soon replaced by a hot, wet tongue. It felt wonderful to have my nipples sucked as I sucked another man's penis. I looked up between the two studs and noticed that James was still sitting on the bed. However, he had removed his boxers, and I was delighted to see he had a large erection, and I DO mean LARGE.

The fingers in my pussy snapped my attention back to the two men making love to me. I sucked on Ed's dick harder now, wanting to make him almost cum, as Troy fingered my already wet pussy. His fingers weren't rough, but it was clear from his touch that he was not overly experienced with women.

"Pity" I thought, because with that body he was made for fucking!

I decided to take charge a little, and so told Ed to lay down on the bed next to James, who was still there slowly stroking that magnificent cock of his. I then told Troy to take off my g-string, and I was totally naked apart from the stockings and suspenders in a room with three men about to fuck me! It made me totally horny to be truthful, and I went to work......

Once in position, I climbed onto Ed's face and positioned my pussy over his mouth. He needed no further invitation, his experienced tongue dipping into my pussy deeply before withdrawing and beginning a sensational flickering motion on my clit. I had Troy stand on the bed over Ed, his dick facing my mouth, and I began sucking him as I rode Ed's face below me.

Suddenly, and after only about twenty seconds, Troy's dick began to spurt in my mouth, and I was shocked that he had started to cum so soon after we started getting into it! Regardless, I swallowed his load like a pro, splashing a few drops onto my boobs for effect, and made a scene of his cock as it spasmed into softness in my mouth.

"Jesus, Troy. What's the rush?" asked Ed, his tongue momentarily removed from it's oral duties.

Embarrassed, Troy moved away and sat on the chair in the corner, watching as his boss returned his attention to my cunt.

James now decided to get in on the action, and he approached me to suck my nipples and kiss me. I had a feeling hookers didn't kiss, but I love kissing, and enjoyed the intertwining of our tongues as his hands explored my boobs. I reached over and enjoyed feeling the girth of his cock as it stuck straight up towards the roof.

It was time to fuck.

Raising my pussy from Ed's talented tongue, I moved forward until my pussy was positioned over his penis. Slowly, I lowered down until my wetness engulfed him, and he took a deep breath as his hands grabbed my hips and he began fucking me from underneath on the bed. We got into a nice rythmn, with my hands supporting my bodyweight and Ed's penis pushing up and down inside me as we fucked on the bed. James kept sucking my tits, until Ed stopped and said;

"Time for the young bloke to take a turn".

I was not unhappy, for his dick was looking even bigger than it had when I first caught sight of it.

I spun my body round on the bed, offering my pussy to James doggie style. In front of me, Ed remained laying on the bed, and so I began my first ever paid threesome! I sucked on Ed's cock, tasting my own juices mixed with his pre cum, as James pushed his monster into me from behind, eliciting a gasp from me as my pussy adjusted to the girth of his cock.

I loved the feeling as I was fucked from behind slowly, my mouth plunging down on to Ed's cock each time James pushed into me deeper. They were good these two, because I enjoyed a thoroughly gorgeous threesome fuck for about ten minutes, before Troy appeared next to us all on the bed, his once soft cock now erect once more! I was impressed!

"Check this out old man" he said, "I'm ready to go again, so how about you let a young stud get some of this fine ass?"

I had other ideas.

"Whoa there stud" I said, stopping him as he tried to takeover.

"Have you ever done a woman in the ass before?" I asked, Troy's eyes nearly popping out of his head.

"Actually, no."

"Me neither", said James, and suddenly I worried that I might not fit that monster into my little butt hole!

"Shit, babe, it's been years since I fucked a woman in the ass, but hey, I'm game if you are! Let's go!" said Ed.

"Ok, but all three of you are gonna have to get me ready first, ok?" I asked.

I stood from the bed and went to the small dresser. Melanie had told me the dresser drawers were full of condoms, lubricants, tissues, etc. I selected the lubricant and three condoms. I wanted to make sure each guy didn't cu in my bum, but also wanted them to last long enough for me to also climax with my fingers as I had my ass fucked.

I got in the doggie position once more on the bed, adjusting the pillows to get comfortable, and passed the lube to Ed, thinking that he would know what to do better than the two youngies.

I was right.

He carefully applied some lube to my anus, easing it in and around the entrance with his pointer finger, before pushing it in and wiggling it round a little. Then, he applied more to the fingers of each of the young guys, and told them to do the same.

James was nervous, and I assumed as his fingers pushed into my ass that mine was the first butt he would ever have played with in this way. I pushed back nastily as he finger fucked my bum, showing him the muscle in there relaxes and expands when loosened up slowly. Troy pushed his finger in at the same time, and suddenly I was letting two strange men stick their fingers in my ass in front of their boss on the bed preparing to fuck them all with my butt.

God I was hot now!

Troy decided he wanted to go first, and put a condom on his erection, before positioning himself behind me.

"Go easy, baby. Take your time. Let's both enjoy it ok?" I said.

"Oooh fuck, I am going to enjoy this, don't worry!" he said, as his hand guided the head of his cock into my ass in front of his boss and workmate.

I moaned and grunted as I felt the first insertion. My bum was nice and wet, and also ready to receive it's invader, but the first time a cock slips into my ass each time I still have my breath taken away at the intensity of that very first invasion.

Troy held me by the hips and moved very slowly, until we both felt my anus relax and then almost engulf his cock as he began to butt fuck me. I pushed back and suddenly I was on fire, with the strange cock fucking my ass slow and deep.

James reached forward and played with my jiggling boobs as his mate ass fucked me next to him. He seemed keen to watch my face as I moaned, grunted and groaned around the cock inside my asshole. He actually reached down to kiss me, and I snaked my tongue around his teeth as I was butt fucked by Troy.

Ed decided to get on the action and began fingering my pussy and clit once more. It was a delightful combination. The pumping motion of Troy in my ass, Ed's hands buzzing my clit and invading my pussy. I could feel Troy's cock being touched by Ed's fingers through the thin membrane that separates my pussy from my ass as I was fucked. It was wild.

I reached down and took Ed's penis in my hand, rubbing the shaft up and down as my ass was fucked by his workmate. It was delicious to feel the stiff hardness of a man's dick as another pushed in and out of my bowels.

James came round in front of us and I offered me his large penis to suck. I marvelled at the way it felt as I struggled to work my mouth around its girth. I managed to lick the head a bit like a lollipop as my ass was being fucked, until Ed told James to sit back on the bed and told me to fuck him.

Behind me, an audible 'pop' came from my bum as Troy eased his dick out of my tightest opening, so that I could move up and ride James' cock beneath me. I eased the head of him into my moist pussy that Ed had made wet with his fingering. It felt lovely, as my lips, then my vagina stretched to accommodate the size of the penis underneath me.

For a few minutes I kissed James on the lips as we fucked in front of his friends, my back to them as they watched my body bounce up and down on the large organ inside me. Then, Ed said he wanted in on this action, and I felt him positioning himself behind me, wanting to fuck my ass.

It had been a while since I had been double penetrated, but the excitement of the experience of being paid to fuck made me want it more than anything at that moment. I reached back and fingered my own bum hole, making sure it was loose and wet once more.

"Ok old man, show me what you got! Butt fuck me while I ride this monster..." I said, putting on the nastiness for effect! I figured if they paid that much, I would give them a show they would never forget.

In an instant he was inside me, the smoothness of his entry evidence that my body was indeed in the mood for some wild, nasty group sex. I managed to push back with my cheeks as my pussy relaxed away from the large dick inside me momentarily, before jamming back on the monster and allowing Ed's penis to glide backwards along my anal passage.

Time and time again we moved this way, our three bodies working in unison. Ed's hands were on my hips, gliding the process of fucking my ass in and out, as James continued to play and fondle my boobs. Troy moved to the side, and again I was offered a cock to suck, which I did with relish! The feeling of all three men's penises inside me was amazing, and I quickly approached my climax!

"Bam!"

It hit me like a brick. My body convulsed, the cock in my mouth received a rather savage bite, and the one in my ass almost got lost in the backwards jamming movement as I spasmed time and time again in my orgasmic state. It lasted almost a full minute, and by the time I had began to subside from my cum, Ed had lost his own control and spewed his load of goo into his condom in my ass. I loved the way he left his cock in my bottom as it pulsed and the seed was spewed forth into the rubber sheath. I enjoyed every single pulsation in my bum, until James cried out, squeezed my boobs and gave a huge push. His big dick also spewed his juices deep into the condom which was buried in my now sopping pussy, and I became blissfully aware of the three of us climaxing almost together as our bodies shuddered then shook, before we collapsed into a cuddling mess on top of James.

Troy was left out, but soon made good by announcing he was cumming too. I stuck my butt high in the air, and invited him to cum on my ass. He ripped off his condom, and then pumped his cock in his fist until the wonderful white semen shot forward, landing on my bum cheeks in small puddles. I knew exactly what to do, I reached back with both hands, and then rubbed the goo all over my ass cheeks, until it made that sexy white lather that a man's cum turns into when rubbed all over the skin.

I loved it! The guys were laughing in an admiring way. I stepped from the bed, danced around in front of the three men who had just cum, and then wiped the white goo all over my body and boobs in front of them.

It was truly a wicked afternoon, and one I will never, ever forget.