MILF Chronicles Ch. 10

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Jill recalls how she was blackmailed into the MILF club.
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Part 10 of the 14 part series

Updated 10/24/2022
Created 09/21/2008
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Chapter 10: Jill's Story

It was another Friday night and I was sitting here alone again. My husband Drew was busy plotting the end of the Alex's club, but then he needed something to do since it all started because he wasn't interested in me. Or more specifically, he wasn't interested in having sex with me. I guess I was tainted now or something. I've tried to talk about it, of course, but he refuses to discuss it. He says that we'll talk about it plenty after it's over. When I ask him when that will be, he just says "as soon as possible", whatever that means. This makes me think about how it all started, a little over a year ago, at Alex's party.

At that time I did not know Alex; I had only met him once. My husband's company was doing business with Alex's company and we had dinner with him. Drew was trying to wine and dine him in order to secure a large contract. Finally after a month of negotiation he was close to signing and Alex invited us to a party at his place. Normally Drew would have declined since he doesn't like big social events, but he felt he needed to accept to keep Alex happy, and keeping Alex happy was very important to him at that time.

I was thrilled, of course, because we seldom went to these kind of events and I rather enjoyed them. Although Alex was about our age, I had heard that he ran with a younger crowd, so I knew I would have to go all out if I was going to fit in. With this in mind I bought a black cocktail dress: sleeveless, plunging neckline, and scooped out in back almost down to the waist. When I tried it on I almost decided against it; I would be showing a lot of cleavage and would not be able to wear a bra with it. After two children my D-cup breasts were going to jiggle provocatively. It stopped about four inches above the knee and showed plenty of leg. I would have to wear full hose with it as well. Ultimately I decided to be a bit daring and bought it.

As an elementary school teacher I was normally pretty conservative in the way I dressed, but this was a special occasion and we would be at a private residence. I was entitled to be a sexy woman once an a while outside the bedroom, wasn't I?

The night of the party when Drew saw the way I was dressed he seemed a bit taken aback. I thought he was going to ask me to wear something else, but after a few unsure moments he just smiled and said I looked great. Later he told me that he had his doubts at the time, but figured that Alex would like the dress and the way I looked, and that erased his doubts.

When we arrived I could see that I had not judged wrong. All of the other women there were younger and were dressed to the nines. In fact, a couple of them had on more revealing dresses than I did. Alex was a gracious host and handed me a glass of wine and Drew a tap beer right at the door. The wine was very good, and almost certainly expensive. The food was also quite good, although I didn't eat much; I was far too busy mingling and talking to people.

The evening was fun and the time flew by. I got a number of complements on my dress and appearance, which along with the wine made me a bit giddy. In fact, by the time the party started to thin out a bit I was feeling very horny. I was looking for Drew so he could take me home and make love to me when Alex approached me and said that he was getting people together for a little party game.

The game was called "dancing in the dark" and, as you might imagine, involved all the participants dancing in a dark room. Alex explained that you start out with your own partner. When the music changes the men move to the next partner and dance with them. Every time the music changes, the men change partners. To add a little excitement to the game people are allowed to "spice up" the dance with some kissing and touching. If someone starts to feel uncomfortable they can "chicken out" and leave the room, but they must take their partner with them.

In my current state this sounded like fun, but I didn't think that Drew would go for it. Alex said that he had already agreed and that it was up to me. I was a little surprised at that, but If he was game, then so was I. After all, it was rare for Drew to go along with something racy like this and I didn't want to be the one to spoil the fun. Besides, he would probably chicken out pretty quickly anyway.

So we all gathered in what Alex called 'the game room'. I noticed that all the furniture had been removed, which seemed a good precaution. Nobody wanted to be tripping over furniture in the dark. Everybody paired up with their spouse or date, the music was started, and the lights were turned off. The music was a slow number, of course, you couldn't really do any fast dancing in the dark. Drew wasn't much of a dancer anyways, more of stand in one place and sway kind of dancer, if you know what I mean.

We kissed a little and he whispered in my ear that he loved me and was glad that I decided to play. When the music stopped he whispered "Have fun" and broke away move to his next partner.

There was a little shuffling and giggling as the men all moved. Suddenly I was aware of a man standing in front of me, trying to figure out how close I was by feeling out with his hands. They just happened to be at the level of my boobs. "Oh, sorry." He mumbled as he 'accidentally grabbed one. Yeah, sure. The next song started and he pulled me into his arms snuggly up against his body.

My mystery man smelled nice and was a good dancer. Before long he bent his head down and started kissing my neck and nibbling at my earlobe. I love having my ears nibbled; it really gets my motor running and this time was no different. When he pulled his head away I automatically moved mine and quickly our lips met. The kiss started softly but increased in intensity as the seconds ticked away.

I was so caught up in the moment that I didn't even notice at first that he had moved his hand down my back and was now lightly squeezing my butt. Since I didn't want any panty lines to show in back I had skipped underwear and was only wearing pantyhose, which I don't normally do. This meant that only the thin material of my dress and hose was separating his hand from my bare butt. I didn't want to chicken out before Drew did, so I just let him do it. It was just a little harmless fun, nothing serious was going to happen in a roomful of people, even with the lights out. Besides, I was enjoying it.

When I felt his second hand join the first one I still was not worried, but when he started to pull my dress up in back I did become a little alarmed. Still I didn't want to quit just yet, so I waited to see what his intentions were. I sure wasn't going to let him remove my dress. Once he had it pulled up completely in back, he resumed his caressing of my ass, except that now his hands were almost on my bare skin. I was a little frightened, but exhilarated at the same time. Our kiss was becoming more urgent and with his crotch pressed into my leg I could feel his manhood start to harden. That's when the music stopped. He let go of me and moved on to the next woman.

The next man found his way to me much the same way as the last and pulled me into his arms. He didn't even wait for the music to start before his lips found mine. For this guy the music was just a pretense because he hardly even danced when the music did resume. It didn't take him long to move his hands down to my ass and pull my dress up again. His assault was more direct than the previous guy. My new mystery dancer was squeezing my ass cheeks more than he was caressing them. This was stoking the fire between my legs, so I didn't really mind. When his other hand found it's way to one of my boobs, however, I was a little less sure of myself.

Should I continue, or quit? When he pinched my nipple through the dress a bolt of electricity shot straight from there to my pussy. I liked that; a lot. I decided then to just let things go for a little while longer. Nothing really serious was going to happen with my husband right in the room, after all.

After that song another man danced with me and acted much the same as the others, as if there was some agreement on warming us all up first. Since there were only four couples playing, my husband Drew returned to me for the next dance. I don't know if he noticed how worked up I was.

"Having a good time?" He whispered as his hands wandered over my body.

"Yes." I whispered back, squeezing his hard cock through his pants. "And I think you are too."

We danced for a while and then he surprised me by pulling my dress off my shoulders and down to my waist. He played with my breasts for a little bit and then the song ended. I started reaching down to pull my dress back up.

"Don't." He whispered. "Leave it for the next guy."

I was too shocked to say anything and when the next man approached me I was still topless. It didn't take him long to figure this out and soon he was pulling on my hard nipples and driving me wild. When the song ended he was sucking on them and squeezing my butt. I was out of breath, my nipples ached, and my pussy was on fire.

I didn't even notice when the next man stepped up to me until he started playing with my tits. I was so hot that I couldn't help checking him out too. When I reached down to check out his manhood I was surprised when my hand touched bare, hot flesh. His stiff cock had already been taken out of his pants; probably by his previous partner! Things were definitely going further than I anticipated. I wondered if Drew has having his bare cock stroked while he feasted on someone else's tits. I should have been jealous, but I wasn't. In fact, I was turned on by the thought of it.

But my lewd thoughts about my husband were interrupted when my "dance" partner pushed my dress down to the ground. Now I was almost naked; all I had left on was my pantyhose and my shoes. When he slid his hand under my pantyhose and onto my bare ass I began thinking that maybe I should stop playing. If things went much further I didn't know if I would be able to stop them from doing whatever they wanted. I was saved from having to make that decision by the song change.

The third stranger also found me with my dress pooled at my feet. He, like the previous two took maximum advantage of my nearly naked body. When I reached for his dick I found that it too was already out, and it it was wet! His previous "dance partner" must have been sucking on it. Suddenly I wanted it in my mouth so I dropped to my knees and greedily gobbled it up. I just love sucking Drew's cock and this was just as fun, maybe more so because belonged to a man I didn't know. I could tell he was getting close to busting his nut when the music stopped.

"OK, everybody, time to quit before things really get out of hand." Alex announced. "I'm going to turn on the lights in 10 seconds, so get ready. Nine, eight.."

As he continued the countdown I regained my senses and pulled my dress back up. I could hear rustling of clothes and zippers being pulled up all around me. I had just gotten everything back and reasonably smoothed out when he reached zero and flicked on the lights. We were all momentarily blinded, but soon recovered and everybody partnered up. Drew gave me a big hug.

"I hope you had fun." He whispered in my ear.

"I just want to get home so I can jump your bones." I whispered back.

"Don't you mean 'bone'?" He chuckled. "Don't worry we'll be leaving soon."

"I hope so. I'm so horny I'm afraid my juice is going to start dripping down my legs." I informed him, and it wasn't an exaggeration.

"So, how far did you let them go?" Drew asked.

Right then Alex stepped up to us. "Hey, break it up." He said jovially. "There'll be plenty of time for that later. We've got one more thing to do before the party ends. Come on."

I wanted to talk to my husband more, but I didn't get a chance because Alex whisked us into the spacious living room where everybody was already gathered.

"All right, now I want to announce a little competition I sometimes hold at my parties called 'Belle of the Ball'. During the party I had all the men rate each of the women on how sexy he thought they were, except of course for his wife-slash-date. The results have been tabulated and the winner will receive these nice earrings." Alex said and held up an open box containing a pair of gold earrings inlaid with pearl.

I couldn't help wondering how expensive they were, but also thought about how nicely they would go with my pearl necklace. I hoped I would win, not knowing at the time that all of Alex's "gifts" had to be earned.

"And the winner is..." Alex opened a card as if he didn't know what was written on it, "Karen and Jill. It looks like we have a tie. Hmmm, what should we do?" He mused. "Can't really split the prize, so I guess we'll just have to have a contest to decide the winner."

"What kind of contest?" I asked innocently.

"I'm glad you asked." Alex replied, smiling. "Since this was a contest on who's sexier I think you two gals should come over here by me and try to look as sexy as possible. Then we'll have the guys vote by holding up their right hand for you Karen, and their left hand for you Jill." He explained.

"I really need you to win this for me, babe." Drew whispered to me, a serious look on his face.

I walked over to where Alex was standing, but I wasn't sure what to do to look "sexy" so I just tried to strike a hot pose like I'd seen in Vogue and Cosmo. Karen did pretty much the same thing and equal numbers of left and right hands were raised. I noted that Drew had his left hand up, which was good for him.

"Still tied. I don't think that's going to get it done girls. Who really wants these earrings?" Alex prodded.

What I didn't know at that point was that Karen was a ringer - she was already in the MILF club and was doing Alex's bidding. So I was a bit shocked when she pulled down the front of her dress and exposed her boobs to everyone.

"OK, it looks like we may have a winner." Alex announced.

I looked back at our audience and all the men now had their right hands up, even Drew. I gave my husband the evil-eye, and although he looked a little sheepish, he didn't change his vote.

"OK," I thought, "if that's what he wants, then fine."

Besides, I really wanted those earrings. So I pushed the straps of my dress down off my shoulders and pushed it down to the floor. As I stepped out of it I did a pirouette and kicked it aside. I could feel my heart thumping in my chest as I stood there in just my pantyhose. I knew my shaved pussy was now on display through the sheer nylon material. I did not dress this way with the intent of showing it to anyone but my husband, which made this very naughty. I should have been embarrassed, but I was too excited.

Now my husband changed his vote, as did a few more, but not all. Still, I had more votes, and that made me feel tingly at the tips of my nipples and between my legs. Karen wasn't done though, she quickly upped the ante by removing her dress and her bra, leaving her completely naked because she was not wearing any underwear. The votes predictably began to shift her way.

I looked at my husband to verify that he wanted me to continue to escalate, knowing that it would end up with both of us nude. He nodded slightly, so I gathered my courage and removed my pantyhose. Again I expected to feel some embarrassment, but I think the heat from my pussy was drowning it out. I was sure that everybody could see the moisture on my lips and the insides of my thighs.

Now we were both nude and the vote was about equal again. What now? While I was pondering my next move, Karen had no such difficulty. She started running her hands over her body, pulling on her nipples and pressing her hand between her legs, moaning a bit to add to the effect. The men that were voting for me defected, of course. At this point I didn't really care about the earrings too much, I just didn't want to lose to this woman.

"So, they want a sex act, do they?" I thought to myself. "Fine then, I'll give them a show!" I walked over to where my husband was standing with his left hand in the air, I noted, and knelt down in front of him. You could have heard a pin drop as I unbuckled his trousers, pulled down the zipper, and pushed both his trousers and underwear down to his feet. Nobody was looking at Karen now. All eyes were on me so I vamped it up a bit. I stuck out my tongue and slowly brought it near the hip of Drew's very hard cock. I paused just short of touching it, then gave it a tentative little lick before pulling my tongue back into my mouth. I made a face like I was trying to decide if I liked the taste, then quickly engulfed his prick with my mouth and began sucking it like a mad woman.

A cheer went up from everyone in the room, man and woman alike. I continued to loudly suck on my husbands cock, bringing a low moan from his throat. The men had stopped voting and I had all but forgotten about the contest. I felt a hand on my ass, squeezing and exploring. A part of me said that I should stop it, but it just felt too good. Then the hand slid under me and found my dripping pussy. Soon a finger was running circles on my clit and I knew I was losing control of the situation.

I stood up and pushed my husband back into a reclining leather chair, his wet cock standing up invitingly. I followed him up onto the chair and impaled my gushing pussy on his rigid pole. I heard a guttural sound coming from somewhere, and then I realized that it was me. I slowly fucked Drew, raising my body up until he almost came out of me, and then slowly sitting back down. I noticed some motion to one side and when I turned my head I saw a long skinny cock. I reached out and pulled it nearer. When it was close enough I bent down and took it into my mouth. I was completely out of control now, but I didn't care. I just wanted cock and I didn't care who it belonged to.

Bent over like that I'm sure my ass was very inviting, and it wasn't long before someone pushed a well-lubed finger into my bum. Then one finger was replaced with two, and finally the head of a hard cock was being pushed past my anal ring. There was some pain at first, of course, but this was hardly the first time I'd been fucked in the ass, so I relaxed and soon the pain turned into exquisite pleasure. While I had enjoyed anal sex many times in the past, this was the first time I'd had a cock in both holes at the same time and the double stimulation was fantastic. I was enjoying myself so much that I kept forgetting about the dick in my mouth, but when I did he pushed it in and out a couple of times to remind me.

The first time I came I had to pull the cock out of my mouth so that I wouldn't bite it off. It was an earth shattering cum and I squealed all the way though it, but neither Drew nor the man in my ass missed a beat. As soon as I was finished with my orgasm I started sucking on the long thin cock again. I had all my holes filled and I was in heaven.

When the guy in my ass started squirting his juice into my bum I guess it was too much for my husband as well because he came at almost the same time. Let me tell you something, if you like the feeling of a cock squirting inside you, then trust me, you will absolutely love it when you have two squirting at the same time. But now that they were spent I climbed off my husband as soon as the guy behind me removed his cock from my ass and backed away.

I grabbed the cock I had been sucking and led the man attached to it over to a sofa. I laid down, opened my legs and said "I want you inside me now." He didn't have to be told twice and soon he was pounding his lovely long cock into my insatiable pussy. Another hard prick appeared near my face and I eagerly accepted it into my mouth.

The next couple of hours are a bit of a blur. I remember having more mind blowing orgasms, although I couldn't tell you how many. I don't know how many men I had sex with, but they came in all my holes and a few even ejaculated on my face and tits. I also remember my husband Drew watching everything and even depositing another load in me, but in my ass that second time. I think at the end one of the women, maybe Karen, used her tongue to clean all the jism off my face, tits, and pussy. I was pretty tired at that time and just laid back and enjoyed the tenderness with which she did it.

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