Milf Chronicles Ch 04

Chapter 4: Sherry Gets Some Training

We were both apprehensive on Saturday morning. Sherry was supposed to be at Alex's house at 1:00 sharp, but without me this time. When she left I made her promise to tell me everything that happened, then I kissed her and my wife walked out the door on the way to have sex with who knows how many men.

It was a nerve-racking afternoon for me; thankfully I had the children to help keep me distracted. At about 7:00 I was starting to get worried. That's when Sherry called on her cell phone to let me know she was on her way home. She sounded tired, so I held back all my questions and just told her I loved her and let her get off the phone so she could concentrate on driving.

When she finally came in the door a little while later, the children joined me in welcoming her home. She gave us all big hugs and acted more or less normal until it was time to put the children to bed a little bit later. Then we sat down and she recounted her day at Alex's.

Sherry's account: I got there just before 1:00. There were several other cars parked out front. I rang the doorbell and Alex escorted me inside and into the living room. Johnny, Marc, and Brian were there along with a woman he introduced as Jill, another MILF in the club.

I was led to one of the extra bedrooms and instructed to change into the outfit laid out on the bed. It consisted of a g-string, a halter top, and a short skirt that zipped up the side. After I changed and went back out to the living room I noticed that Jill was wearing the same outfit. I didn't know what this meant, but I was nervous. Alex gave me a glass of wine to help me "loosen up". I took a big gulp as a bracer and sat down in the only available chair. It was then that I noticed that all the furniture was arranged in a large semicircle.

"All of our MILFs are required to know the art of strip-tease and lap-dancing, Sherry. You will be learning this art today and Jill will be your teacher." Alex announced. Then he pushed a button on a small remote and some bump-and-grind music right out of a cheap movie started playing.

He nodded at Jill and she got up and started dancing near the center of the circle created by the furniture. Alex told me to study the way she stripped. Jill helped by pointing out the way she moved, how she made eye contact with the audience, seductive looks, etc. as she danced. I drank my wine and tried to concentrate on what Jill was doing. From what little I've seen in movies and such, she was pretty good.

After a few minutes she motioned for me to join her. I started dancing too, trying to copy what I had seen her do. She danced in front of me, encouraging me and helping me to get it right. Still, she said I was a little stiff, so she moved around behind me, putting her arms around me with her hands on my belly. Her body was pressed up against mine as we danced together. At first all that body contact was distracting, but after a few minutes I started getting into the rhythm and we started moving as one.

Then she started using her hands to show me how to move my upper body, arms, and hands. When she took my hands and ran them down from my neck across my breasts, um, tits and down across my belly, a shiver shot down my spine right to my pussy.

The men all had smiles, so we knew they liked what they saw. Now Jill danced back in front of me and began to run her hands over her own body in a very suggestive way. I tried to copy her and still dance the way she had showed me, but it wasn't easy, I was still very nervous. After all, a married woman was not supposed to do this sort of thing, or at least not in front of men that weren't her husband.

So I tried to tune out the surroundings and just feel how my hands made my body feel. Soon my nipples started tingling as they hardened and my pussy started to juice up. Then I noticed that Jill had untied the top string on her halter and was teasing the guys by flashing her tits and then quickly covering up again. She danced over to Alex and turned around. He pulled the tail on the bottom string and now her top was only being held up by her hand.

Jill danced moving forward a few steps back toward the center of the circle, then she threw the halter over her head in the general direction of the men. Putting her arms across her chest she turned around and danced for a few seconds before throwing up her hands to reveal her bare tits to the men. She bent over and shook them, squeezed them, and pinched her nipples, keeping them hard. Then she looked at me and I knew it was my turn.

I decided to do it a little differently and untied the bottom string on my top. This way I could just leave it hang and still dance without holding it up. As I swayed to the music the top swished back and forth giving them a little peeks at my tits. I danced over to Johnny and turned around. He got the idea and started pulling on the top tie, but I didn't wait for him to finish. Instead I stepped away leaving him holding the halter by the one tie. I danced a little with my back to the men, then turned around to face the men. Like Jill I fondled my tits and shook them for our audience.

Jill started playing with the zipper on her skirt, lowering it and raising it, teasing the guys. Finally she unzipped it completely and tossed it Brian. I knew it was my turn next so I teased them for a while too before removing my skirt. Now we only had on the skimpy g-strings which did not hide very much.

Alex announced that although all the exotic dancers in our state were only allowed to strip down to their g-strings, in the MILF Club we were expected to remove everything. With that said Jill turned around, bent over, and started slowly pulling the string like waist-band down over her butt. I did the same thing, thinking it would be easier for me if we did it at the same time. From the sounds of it the men seemed to enjoy the double action.

When we had the tiny pieces of underwear at our feet we stepped out of them, looked each other in the eye and spun around. We danced totally nude for them for a little while and then Jill came up to me and put her arms around me, rubbing her tits against mine. It was a strange feeling, but not bad.

She bent her head down and whispered in my ear, "They like to watch us play with each other. Don't worry, it doesn't have to be real. It just has to look real. Illusion is a big part of the MILF club."

Then she kissed me; lightly at first. I was a bit shocked since I had never kissed another woman before. It was different than a man's kiss; softer and more sensual. She kissed me again, a little bit harder and longer. I found myself kissing her back, just to make it real of course. But if that was true, then why was my pussy throbbing?

Jill ran her hands over my body, squeezing my butt and fondling my tits. I was feeling weird about the whole thing: turned on, embarrassed, and ashamed all at the same time. I decided that I had better reciprocate, again to make it look real, so I started running my hands over Jill's body as well.

I understood then why men liked women: they are smooth and soft and very sensual, not that I turned gay or anything, it was just one of those "aha" moments. We kissed and groped each other like this for a few minutes and then Jill bent down and took one of my tits into her mouth. She swirled her tongue over my nipple, making it even harder than it was, although I would not have believed it possible. You know how I love having my nipples licked; it was wonderful. As she did this she also ran her hand over my bare pussy, her touch sending shivers up my spine.

That was nothing though, compared to the shocks I felt when she slipped a finger into me. The men devoured us with their eyes as Jill finger fucked me while sucking on my tits. Just as I started feeling my climax build, she removed her finger, running it up my slit and over my clit, making me jump. Standing up straight she put her finger into her mouth and made a show of sucking my juices off it.

I knew it was now my turn, so I gathered up my courage and bent over to bring my face level with her tits. They were larger than Cheryl's and I think a little larger than mine. I opened my mouth and put it over one of the soft mounds, sucking it in slightly. I ran my tongue over her nipples like she had done to me and was rewarded with a soft moan from Jill. I felt some perverse pride at being able to cause that reaction.

I was having trouble bringing myself to finger her though, so after a minute or so she gently took my hand by the wrist and guided it down to her bare mound. When it got there she put her hand over mine and rubbed it on her pussy. It was smooth and soft and warm, warmer than I had expected. After a bit she took her hand away, but I kept mine there.

She was being so gentle with me, trying to make this go easy, and I wanted to show her my appreciation, so I put aside all my doubts and pushed my index finger into her well lubed hole. Sherry-slut was now fully in control and I started sliding my finger in and out, making sure to pat her clit with my palm every time I pushed back in.

By the sounds she was making I could tell that Jill was really enjoying herself. It was making me excited knowing that it was me give her all that pleasure. After a minute or so of this she pulled my face away from her chest and whispered that we had to move on. I reluctantly removed my finger from her dripping pussy and, like her, put my index finger into my mouth.

Her juices tasted a bit different than mine, but it was not unpleasant. I sensuously sucked all her juices off my finger the way she had earlier. The men hooted in appreciation.

"Time for the lap dances girls. Jill, you take Brian. Sherry, watch Jill and then practice on Johnny." Alex ordered.

I watched as Jill stepped over to Brian, leaned over him putting her hands on his shoulders, and shook her tits in his face. This was just a quick tease, though because she stood back up, turned around and wiggled her ass at him. As she sat down in his lap she said "You always want to tease them a little before you actually sit down in their lap."

Jill pushed her butt up against Brian's crotch and rubbed it in slowly to the beat of the music. As she did this she leaned backward against his chest and tilted her head back onto his shoulder. "Sometimes you have to encourage them to put their hands on you." Jill stated. I doubted that was really true, they probably get off on the idea that we are seducing them.

Jill guided Brian's hands to her tits and when he started to play with them she reached above her head and pulled his head down to her neck which he started nibbling. I had to admit, she did make it look very erotic. "OK, you try it now with Johnny." She told me.

I went to Johnny and tried to copy what I had seen Jill do. Soon I was grinding my ass into Johnny's hard cock as he pinched and pulled on my nipples. Out of the corner of my eyes I saw Jill get up, turn around, and sit back down on Brian's lap facing him in a straddle position. I copied her and watched to see what she did next.

Next Jill pushed her tits into Brian's face and dragged them back and forth across his mouth and nose. It didn't take long for him to stick out his tongue and she took advantage of it and ran her nipples across it over and over. At the same time she reached down and started squeezing his cock through his pants.

I followed her lead, except as soon as I put my tits within range of Johnny's face he started sucking on them. And soon after I started rubbing his hard-on through his pants he reached down to unbuckle and unzip his pants. In no time at all I had his hard cock in my hand. I couldn't believe how hot it was; it felt like it was burning my skin.

"Looks like you got ahead of me." Jill commented as she unzipped Brian's pants and fished out his engorged manhood.

I was not sure I could take the next step. That night at the party I had more to drink and I was being sort of forced into it. Here I was almost completely sober and acting of my own "free will". Even though I had had sex with Johnny before, all my doubts started coming back.

I looked over and saw Jill lowering herself onto Brian's cock and realized it was now my turn. I was going to get screwed again by someone other than my husband and this time I was going to be the instigator. I raised myself up on shaky legs, reached down to aim his spear at the entrance of my slick hole, and slowly lowered myself down. I felt his cock head slip past my labia and into my wet canal, and it felt good, even though I knew it was wrong. As I slowly lowered my body down I felt every inch of him enter me.

About halfway down I reversed my motion and raised myself back up until his dick almost slipped out. When I slammed all the way down, taking him to the hilt, he threw his head back and hissed "Yes". I paused there for a moment luxuriating in the feeling of having my pussy stuffed full of hard cock. Sherry-slut was back in force.

I started riding him with real vigor now, mashing my tits into his face. He obliged me by sucking on them and nibbling on my nipples. I glanced over and saw Jill doing the same thing, but she did not seem to be enjoying it as much as I was. I kept this up for a few minutes and then I noticed that Alex and Marc had their cocks out and were stroking them.

I got up off of Johnny and crawled on my hands and knees over to Alex. I grabbed his cock and licked it from the root to the tip several times before taking it completely into my mouth. Johnny came up behind me and picked up where we had left off. Marc walked over and stood by the chair that Brian was sitting in and offered his cock to Jill. She took it into her mouth and began to greedily slurp it in and out.

Over the next ten minutes or so we switched positions and partners several times, but eventually all four men had shot their loads into one of our holes. At that point they declared a break and told Jill and I to make them something to eat. Jill picked up one of their shirts and pulled it over her head on the way to the kitchen. I did the same and followed her.

In the kitchen I told her that I didn't cook much, but she said she was a chef and to just follow her instructions. In no time she had whipped up a wonderful smelling shrimp stir-fry and I had rice going in the cooker (even I could do that). When the men smelled it they filed into the kitchen wearing just their briefs, although Johnny wore boxers I noticed.

They sat down at the table and we served them. Every time we came near them they patted our asses, copped feels of our tits, and occasionally sneaked a finger into our pussies. They didn't allow us to eat until they were done. Jill and I split about a single portion between the two of us.

"Wouldn't want my MILFs to get fat." Alex noted.

After that they wanted desert: us. They had Jill and I lay out on the table on our backs. Then they brought over some whipped cream, chocolate sauce, and some fruit. For the next half hour or so they adorned us with these sweets and ate them off of us. They also put the whipped cream and chocolate sauce on their semi hard dicks and made us lick it off. By the time we were done they were all hard and ready to go again.

Alex announced that Jill and I would now compete in a "cum-off". He had each man draw from a deck of cards. Marc and Brian got the lower two cards and were teamed with me, while Alex and Johnny pulled the highest two cards and were teamed with Jill. The objective, in Alex's words: "Use the slutty MILF to cum as quickly as possible."

Now they had each already orgasmed once, so they would have substantial staying power. Marc laid down and had me climb on top of him so that Brian could take my ass. Next to me Alex was taking Jill doggy style while she gave Johnny a blow job.

Alex actually shot his load first. He even pulled out and deposited it on Jill's back to prove it. Johnny then lubed up her ass and started pounding his long skinny cock into her back door. While that was going on Marc and Brian developed an alternating rhythm on me. I lost count of how many times I came, but it was a lot. Near the end I was cumming almost continually. I think that's what finally pushed Marc and Brian over the edge and allowed them to win the contest.

After that we all climbed into Alex's huge tub and soaked, enjoying the water jets. The men still groped us, but there was no more sex. When we climbed out I was still a little sore, but I was feeling much better – and clean. Jill, Brian, Marc, and Johnny all dressed and left.

Alex allowed me to get back into my clothes (the ones I arrived in), except without my underwear. Apparently MILFs don't wear underwear, at least in his world. Then he drove me into town to the mall. When we got there he gave me a credit card and told me what the PIN for it was. I didn't know why until he led me to an ATM and told me to get a cash advance for two hundred dollars. He stood back and watched me do this from a distance, but at the time I didn't quite know why.

Next he led me to a Victoria's Secret store and introduced me to the owner, Beth. He told her that I was a new member of the club and needed some "appropriate MILF attire". He must have done the same thing with the rest of the women in the club because she knew exactly what he wanted. Beth was about 45 or so and had a friendly way about her that put me at ease. After she got my measurements she went about the store collecting various items. When she had amassed a small mountain of articles she led me into the changing room and told me to remove my clothes.

I hesitated and she said, "No need to be shy honey," and in a more of a hush, "it's not a good idea to make Alex wait."

I pulled my t-shirt over my head and started unbuttoning my jeans.

"I was one of the original recruits to the club." She confided as I pushed my jeans down my legs and stepped out of them. "So I have a good idea what you're going through. Put this on." Beth handed me a black leather bustier.

I needed a little help putting it on since I had never worn one before. After that she helped me put on a small matching leather skirt before opening the door and gently pushing me out. Alex had me model it for him, complete with a full turn so he could see what it looked like on me from all sides. I was embarrassed to be standing there wearing so little outside the changing room, even if it was in the back of the store. I could see I was mostly shielded from the mall traffic, but I was still nervous someone would see me.

Next we tried a French maid's outfit and then a camisole type of thing with skimpy panties. As I worked through the pile of lingerie the outfits got skimpier and skimpier. Eventually I was forced to walk out of the changing room wearing only a shelf bra, a pair of crotchless panties, thigh high stockings, and three inch "fuck-me" pumps. This meant my tits and pussy were almost completely exposed. When I looked in a mirror I thought I looked like a whore. I blushed furiously, but endured it. Fortunately that was the last outfit and no other customers had entered the store during my show. At least, I didn't think so.

During this degrading process Beth told me that Alex "suspended" her club "responsibilities" so that she could concentrate on running the store. She said the truth of the matter was that he found younger and better looking women to replace her. Apparently he provided the loan she needed to buy the franchise license and open the store. In return she provided clothes to all the women in his club for cost. She told me the club is really about power, with sex being only one manifestation of that power. I got the distinct impression that he had his hooks into other business owners as well.

With the degrading lingerie modeling finished Alex told me to pay for all of it with the credit card he gave me earlier and Beth packed all the items into a couple of large bags. I was kind of self-conscious walking out of the mall with such large Victoria's Secret bags, I mean, what must people think? What kind of woman would need that much lingerie?