tagMatureVoyeuring a MILF: The Sequel

Voyeuring a MILF: The Sequel

byIrish Moss©

"I have no intention of fucking Jen anymore," I told my companions as we sat in the bar.

"Who are you and what have you done with my immoral friend?" Jim asked, looking at me suspiciously.

"She started dating some guy she goes to school with," I continued, "but told me she still wants me to come around. I told her I'd have to think about it. I don't want to be like her mistress. Besides, this frees me up to pursue someone else."

"Who'd you have in mind?" Rob inquired, knowing full well that I wouldn't care about being free to pursue unless I had already thought about whom.

"Jen's mom," I replied nonchalantly, taking a sip of my beer. I thought Rob was going to shoot beer out of his nose.

"That's my boy." Jim said, smiling widely. "I'm sorry I ever doubted you."

Without telling them of the two times I'd voyeured her, I explained my reasoning for my interest in Jen's mom. I reminded them how hot she'd looked that night we'd been busted at Jen's house and informed them that, according to Jen, there was no man in her life. I told them I'd rather be involved with an experienced MILF than with a high school girl with a boyfriend.

"I assume you have some sort of plan," Rob said, pragmatically.

"As a matter of fact, I do," I confirmed, "and you are going to help me." I went through my plan to show up wherever she went out for her next girls' night and play it by ear once we got there. I hinted that Jen's mom might have a few horny, experienced girlfriends with her. That was enough for my boys to be down with the plan.

"What's Jen's mom's name, anyway?" Rob asked.

"Marsha," I replied.

I'd stayed in touch with Jen, maybe giving her false hope so that she'd call the next time her mom went out. Sure enough, I got a call asking if I'd come over one Thursday night. Once I'd confirmed that her mom was just going out for the evening, I declined, saying it just didn't feel right to me. I suggested she invite her boyfriend over instead. I called my boys and told them to be ready. My plan was to follow Marsha to her destination, then pick up Jim and Rob and head back over there together.

I was not disappointed when Marsha turned into the parking lot of The Shuffle Inn. I'd been there many times, so I knew the layout and the type of people in there. Jim, Rob and I would fit in and we'd likely be very appealing to a group of older ladies compared to the regular clientele. I took off to pick up Jim and Rob and we were back within half-an-hour. Once inside, Jim grabbed a pool table, Rob grabbed three beers and I did some reconnaissance. Marsha was with two other women just inside the bar. Her friends were of similar age and similarly dressed. The ladies had definitely noticed us coming in, but the question remained whether they were noticing us out of interest or because Marsha recognized us. We would see.

There was no question during our first game of pool that the ladies were paying attention to us, but they never approached us. It looked as though they were drinking margaritas, which I confirmed with their waitress. Rather than being cliché and sending the next round over on us, I had the bartender make up the next round and brought it over myself. They were speechless when I walked over with the tray, but I'd already planned what to say to break the ice.

"Ladies," I started, setting their drinks down, "my friends and I all agreed that this bar has never looked as lovely as it does tonight. These drinks are our way of saying thanks for vastly improving the atmosphere of this dive." I made sure that when I made eye contact with Marsha, I held it and smiled, taking in her features from a much closer perspective. I felt a rise in my jeans. "If you are interested, please feel free to join us for a game or two of pool."

They thanked me and I walked back to the bar to return the tray before going back to the pool table. Jim and Rob confirmed that they'd watched my ass all the way across the bar. We didn't watch to see what they did, so we were pleasantly surprised when they got up and came over by us. They grabbed a tall table close to the pool table and pulled up tall chairs around it. We thanked them for joining us and introduced ourselves. If Marsha recognized any of us from her basement, she didn't let on, even as we said our names. Marsha's two friends were Wendy, who had shoulder length brown hair, big boobs under a black shirt and a black and white miniskirt, and Beverly, who was bleach-blonde and thin in a tight black dress. We invited them to play with us, but they just wanted to watch at first. We continued our game while flirting with them, with me paying particular attention to Marsha. I would have been happy with any of them, but I wanted to take my shot at Marsha first. If she wasn't interested, I'd move on.

Sitting on those tall chairs, the ladies were showing us a lot of leg in their short skirts and we sure weren't complaining. I think the three of them were getting more attention in general sitting up there, so we were pleased that they were hanging with us. We played a little pool, did a little drinking and flirted outrageously. Everybody seemed to be on the same page – they appreciated our attention and we appreciated their company. Gradually, we sort of paired off. Marsha seemed pleased that I was focused on her while Jim ended up with Beverly and Rob with Wendy. I managed to get Marsha to play me in a game of pool, assuming she was good because I knew there was a pool table in her basement. I thought maybe I'd take things up a notch and asked if she wanted to make the game interesting. She asked what I had in mind, appearing quite intrigued by the proposition. Indicating her "fuck me" pumps, I told her I thought they would be tough on her feet during the game, so if she won, I'd give her a foot massage. I wasn't planning to win. I knew a foot massage would also give me a nice view of her stocking tops and panties. She asked what I wanted if I won. I didn't really care, so I shrugged and said, "Lap dance?" Marsha laughed, then scattered the billiard balls all over the table as she broke. This may have been meant to intimidate me, but as I said, I suspected she'd be good and I had no intention of winning.

We played a good game; I didn't have to throw it away completely. To be honest, I couldn't tell you if I even helped her win at all; she may have beaten me fair and square. I was happy that she called me on the bet and we retired to the tall chairs she and her friends had been occupying. She left her shoes on the floor and placed her feet in my lap. As I massaged her feet and we talked, I noticed that Rob and Wendy were missing. I wondered out loud where they had gone.

"Hopefully, they are out in her car and he is giving her a good fucking," Marsha commented. She went on to explain that Wendy was unhappily married to a slug of a guy who would rather watch ESPN than fuck his wife. She wasn't ready to give up on the marriage, but Marsha suspected that getting some action on the side might start to steer her in that direction. She had been hesitant about taking that step but maybe tonight was the night. I assured her that Rob was an honorable guy who wouldn't do anything to hurt her. I hoped that whatever happened between them would be good for both of them. I asked what Beverly's story was. Marsha explained that Beverly was happily divorced with no kids and her own place. I filled her in a little on Jim.

As I worked on her feet, I was getting a really nice view up her skirt, which was giving me a rise in my Levi's. Her stocking tops were barely above the hem of her short, black skirt and her panties were black. There was a band of her white flesh visible between the tops of her stockings and her panties. I finally told her what a turn-on her thigh-highs were and that if we were sitting on my couch instead of in a bar, I'd already be going down on her. Her eyes got a little wide at that revelation and she probed my lap with her foot, finding the bulge there.

"My car is a bit more private," she said softly. "We can follow Rob and Wendy's lead, if you want." I definitely wanted. She slipped back into her shoes and we found Jim and Beverly to let them know we were stepping outside to get some fresh air. They both knew what we were up to. As we headed to her car in the parking lot, she lead me around what turned out to be Wendy's car. Through the steamed up windows, we could see writhing flesh. That was a good sign. Even though I knew which car was Marsha's, I let her lead me so I didn't give that away. She unlocked her door, but before we got in, I took her in my arms and brought my lips to hers.

I couldn't believe I was actually making out with Jen's mom! Not only was the flesh I had admired through her window now within my arms, it also seemed like a pretty safe bet that my hands would soon be caressing that flesh. As if that wasn't enough, she also seemed pretty into me. In the words of Hannibal Smith, "I love it when a plan comes together."

"I have to ask you a favor," she said tentatively, breaking our kiss but remaining in my arms. Being there with her was more than I could have asked for, so I was open to any favors at that point. "I want to fuck you so badly, but I really don't want it to be in my car. If you are still interested in going down on me, I promise I will absolutely return the favor, but, as sad as it sounds, it has been a long, long time since my bed has seen any action. Can tonight just be an appetizer, so to speak, with the main course this weekend?" Looking deep into her eyes, I told her that even if she'd said she just wanted to make out tonight, I would still have been all right with it. The fact that I was still going to get to lick her pussy and she was going to reciprocate was a total bonus. "Good," she said, "because I am so wet right now that I desperately need release...and soon!" She kissed me hard before opening her car door and crawling into the back seat.

I followed her and closed the door, sitting beside her in the back seat. I leaned in to kiss her while sliding my hand up the inside of her thigh, going from stocking across bare flesh to her panties. Her panties were indeed very damp, so I didn't waste any time lowering my head as she spread her legs apart. I didn't even bother taking the panties off, just pulled them aside to reveal that dark blonde bush. I slipped two fingers into her immediately and pumped them in and out while my tongue sought out her clit. Her hands were in my hair, gripping it tightly, when I started licking and sucking her clit. She moaned a deep, throaty moan, pushing her hips toward my face. The scent of her arousal filled my head while I enjoyed the pungent taste of her pussy. She was flowing with juices, lubricating my fingers as they pumped in and out, making me think that fucking her was going to be absolutely awesome. I just kept licking and sucking her clit, glancing up to see the ecstatic look on her face as she whipped her head back and forth. My cock was ready to burst out of my jeans but, although I was looking forward to slipping it into her mouth, I was also very pleased to be where I was. I relished the taste and feel of her pussy and the effect I was having on her. She was getting louder and louder, sounding relieved and aroused at the same time. Her hips were starting to buck at my face faster and faster as I devoured her pussy. She definitely wasn't sexually reserved; she was noisy and active, leaving no question as to whether she was having a good time.

The closer she got to orgasm, the more engorged her pussy felt around my pumping fingers. It was as though all the blood in her body was in her most intimate of areas. From the sound of it, all of her nerve endings had relocated there as well. My technique didn't vary much, seeing as I was having so much success with it. I kept licking and sucking her clit, no matter how wildly she was flopping around in the back seat, and kept pumping my two fingers in and out of her increasingly slippery hole. Her cries got to where she was sounding almost desperate for relief. When she started arching up off the seat, I suspected that she was right on the precipice and anticipated enjoying her orgasm with her. Sure enough, she tensed up completely, sounding as though she was also holding her breath, then let out a ragged moan as she eased herself back down to the seat. Her body spasmed as she rode out her orgasm and her pussy pumped out copious juices for my consumption. Finally, she let out a long, relieved-sounding sigh and went completely limp.

I raised my head and slipped my fingers free, letting her panties slide back into place over her blonde curls. I sucked my fingers as she recovered, my cock still throbbing in my jeans. She finally seemed to catch her breath and sat up, blinking as if the blood was finally returning to her brain. I pulled my fingers free of my mouth as she leaned over to kiss me, thanking me over and over and dropping a hand to my crotch.

"And now it's my turn," she announced as she focused her gaze on my lap and put both hands to work opening my jeans. I lifted my ass once she had them open, allowing her to slide both my jeans and my underwear down to my knees. She took only a few seconds to familiarize herself with my rigid cock before plunging it into her mouth. She moaned as if it were the best thing she'd ever tasted while I moaned at the incredible feeling of her mouth sliding down and engulfing my cock. She had one hand gently massaging my balls while the other held the base of my cock, pumping it up and down as she slid my cock in and out of her mouth. I thought about the two times I had looked through her bedroom window and admired her naked, mature body, never thinking I'd have the opportunity to do any more than that. Now her hot mouth was sliding up and down my cock, ready to swallow my load. I lay my head back and just enjoyed her superior oral skills, feeling an orgasm slowly building up deep within me.

I didn't really need to do anything; Marsha had it all under control. She also seemed to be enjoying it as much as I was. I was muttering encouragements as I relished the feel of her warm mouth wrapped around my rod. As my orgasm got closer, and believe me it didn't take that long, I couldn't help but raise my hips in rhythm with Marsha's sucking. She gave such amazing head that even before I'd blown my first load into her mouth, I looked forward to sliding my cock into her mouth on many future occasions. I began to move my hips faster, indicating that my orgasm was impending, and she picked up on it right away. She adjusted her movements accordingly and prepared to receive my bounty. My cock began to swell and my breath got shorter and shorter. I had one hand on the back of her head and was pushing her down as I pushed my hips up. With a cry of relief, I exploded into her mouth, releasing blast after blast of cum, which she dutifully swallowed down.

When I finally collapsed back onto the seat, I tried to catch my breath as she licked my shrinking cock clean. She raised her head and seemed lost in the moment while I pulled my underwear and jeans back up. She asked if I was ready to go back in, but I told her I wasn't quite ready. I reached under her skirt and asked her to lift up. Without question, she did, and I slid her panties off. She looked at me inquisitively and I told her she'd get them back the next night, then held them to my nose and inhaled her musky scent before slipping them into my pocket.

We crawled out of the car and Marsha locked it back up before we headed back inside. Rob and Wendy were back, sitting with Jim and Beverly. They smiled knowingly as we returned to the table. Marsha invited her friends to join her in the Ladies' Room while I sat with Jim and Rob. Rob got laid, obviously, and was aware that Wendy was married, but it didn't bother him; he'd determined that he had no prejudices when it came to fucking married women. Jim was going home with Beverly that night; they hadn't even kissed, deciding to save it all for when they got to her apartment. I filled them in on my exploits with Marsha and our plans for the weekend. They were impressed that my plan had worked out and now I was going to be fucking the mother of a girl who until recently I had been fucking. I had a feeling the weekend was going to be outstanding.

When we decided to call it a night, Jim and Beverly took off in her car for her place while I made out with Marsha and dry-humped her against her car. Marsha finally said we had to stop because I was getting her all worked up again, so I waited until she was in her car and had it started before I headed over to my car. Wendy and Rob were making out hot and heavy and it was a couple of minutes before he finally joined me. We headed home feeling pretty damn good about the way our night had gone.

I had given Marsha my work phone number so that she could call Friday and let me know when to come over that night. She called just after lunch and wanted me at her house around 7pm. Once I knew Jen was home from school, I called her to see what she was up to for the weekend, just out of curiousity. She told me that she was spending the weekend with her dad, so she wouldn't be around until Sunday afternoon. I debated whether I wanted to go over a little early and watch Marsha get ready for our date through her bedroom window but I decided against it. I figured I'd be seeing her naked up-close-and-personal soon enough, so I didn't need to peek in at her. I had some time once I was home from work before I had to head over, so I showered and slipped into jeans and a shirt that I didn't expect to be wearing for very long. I didn't even bother with underwear. I was very excited, in more ways then one. I wondered if we'd even make it to the bedroom or if we'd end up fucking right on the living room floor. I quit wondering and got in my car to drive over.

Pleasantly surprised doesn't even begin to describe my reaction when Marsha opened the front door. She was dressed to fuck, wearing a red bustier with black garters attached to black hose. Under that she wore a red and black g-string and a pair of black spike heels. Her tits were practically spilling over the top of the bustier, which reminded me that I still had not even touched them, much less sucked her luscious nipples. The bustier cinched in her waist, but ended above her full hips and, as she led me across the living room, I could see how the heels accented the muscles in her legs and tightened up her ass. She definitely had a strut in her walk as she headed to her bedroom, while I followed behind her shedding my shirt, shoes and socks.

Her bedroom was dimly lit; the overhead light was off but a variety of candles was spread throughout the room. The bed was turned down and the sheets appeared to be, and I know it sounds cliché, red satin. I stopped just inside the doorway so I could watch Marsha crawl to the middle of the bed. My cock was hard as a rock as I stared at her ass with only a red string running between her cheeks. As she stopped in the middle of the bed and turned to face me, kneeling, I was opening my jeans to release my python. Her eyes were locked below my waist as I pushed my jeans down and my cock sprung up to point at her. My cock bounced as I walked over to the bed and climbed on, walking on my knees over to her. She reached out to stroke my tool as I leaned in to kiss her, my hands going to her waist. Sliding my hands around to her back, I started to unfasten the hooks holding her bustier together. She released my tool and worked on unhooking the garters from the stockings while we continued to make out. As I pulled the bustier away from her, breaking off our kiss, I told her that she looked incredible wearing it and that I hoped to see it again, but I was anxious to get to her tits. She was okay with taking it off because she said she could breathe again. I started pushing her backwards onto the bed as we made out again, then slid down to fondle, kiss, lick and suck her big tits.

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byIrish Moss© 3 comments/ 136571 views/ 13 favorites

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