Voyeuring a MILF: The Prequel

Jen's mom was a babe. Not a supermodel babe, but as far as friends' moms went, she was the one we all lusted after. Blonde. Voluptuous. She must have been on a date that night, because she was all dolled up, looking the hottest I had ever seen her. She was also livid. I don't know if Jen wasn't expecting her home this early or just didn't quite get us out in time, but she was none too happy to find us sitting around the basement drinking. Jen was only 18 and still in high school.

We gathered our things and were quickly heading out when the bag full of alcohol I was carrying slipped. Jen reacted quickly, reaching out to help me and wound up with a handful of my crotch by mistake. We were both caught by surprise, then she got a gleam in her eye and reached in for a second grope. My hormones were already rampant from seeing her mom in a tight, short, black skirt, so her first contact had sent most of the blood in my body to my nether regions. The true grope had me hardening in her hand.

"Jen, I think you are in enough trouble as it is." I told her, "As much as I am enjoying your attentions, I don't think you want your mom to catch us like this." She reluctantly let go and the smile left her face. "I'll call you this week." I promised, adding, "We can pick up where we left off." She smiled again and I leaned over and kissed her.

It was later the next week when Jen let me know that her mom was going out again. She had promised that she wouldn't have her friends over again, especially since it was a school night, but she wanted me to come over since we had some unfinished business. She didn't know what time her mom was planning to leave and knew that it would look too obvious if she asked, so I said that I would just park down the street and watch for her car to leave.

I did park down the street, but rather than sit there for who knows how long, I got curious and took a walk over to Jen's house. It was mid-winter, but it was a mild night with no moon, so I was able to prowl around outside of the house checking each room with a light on. The first room I found someone in was Jen's. She was standing in front of the full-length mirror and I thought at first preparing herself for my visit. As I watched, though, I realized that what she was doing probably wasn't in preparation for me, but more likely as a result of thinking too much about the night ahead. She was dressed in a black long-sleeved shirt and black knit pants and her hands were cupping her breasts through her shirt.

My cock began to stiffen as I realized what she was up to. She seemed to be kneading her tits, which was confirmed when she pulled her shirt up, holding it under her chin while she undid the front clasp on her bra. The pink of her nipples and areolas was quickly hidden again under her hands as she cupped her now bare breasts and began to fondle them again. For a few minutes, she rubbed her palms over her tits and gently pulled on her nipples before dropping her hands to her waist. She pushed her pants and panties down to her knees, letting me simultaneously see her ass and the reflection of her light brown bush. She put one hand to work on her pussy while the other went back and alternated between her tits. I had a raging hard-on, which I released from my jeans and began to stroke in my fist.

I continued to watch, my gaze shifting from her tits to her ass to her pussy and even up to see the look of pleasure on her face. My orgasm was quickly approaching as I watched her and the pace of the hand between her legs was increasing in speed. She dropped her other hand between her legs as well, her shirt dropping to cover her tits again. It didn't matter that I couldn't see them, though, because I was already past the point of no return. I watched her ass as she humped her hands and at about the point when her knees seemed to buckle, I was shooting a load against the vinyl siding. I continued to milk my cock as my spurts weakened and I started to go limp, watching Jen shudder through her orgasm. As she pulled her pants and panties back into place and refastened her bra, I was tucking myself away as well.

Once Jen was presentable again, she opened the door and left the room. I waited for a minute or two to see if she was coming back, but got to thinking that if her mom was going out that night, she might be looking as hot as the last time I'd seen her. I decided to continue checking windows and made my way around the back of the house. The next window I looked in appeared to be Jen's mom's room, but it was currently empty. I didn't have anywhere else I needed to be, so I just waited. I didn't think she would have left without me hearing the door or the car or seeing headlights, plus her bedroom light was still on. Even if I just got a peek of her as she reached in to turn off the light before she left, I felt it would be worth it.

As it turned out, it was well more than worth it. After a few minutes outside the window, Jen's mom walked into the room and I'm surprised she didn't hear my eyeballs bang against the windowpane as they bugged out of my head. She came through the doorway wearing a towel on her head and nothing else. She wasn't walking directly toward the window, but I got essentially a full-frontal view. Her tits were big, with some sag to them and more freckles then I would have expected. Her stomach had a slight pooch, not unexpected for a woman in her forties who'd had two kids almost twenty years prior. Her pussy was covered with well-groomed dark blonde hair and her thighs were just a little thick. I couldn't believe it but my cock was starting to stir again already.

She stopped at her dressing table and pumped a handful of lotion, which she began spreading over her breasts. I just about groaned out loud as she rubbed the slick lotion into her large tits, massaging them over and over, her big, hard nipples flicking each time her palms passed over them. She continued rubbing lotion over her stomach and down her legs, her breasts swinging as she leaned forward. She finished with her thighs and ass, then stepped over to her dresser. From a small drawer, she pulled a few select items, which she set on the bed. I didn't recognize what they were at first, my attention still mainly on her tits and pussy. When she held one of them up, I realized that it was a black thong panty. She straightened it out and stepped into it, her tits swinging again but her pussy now covered. I opened my jeans and had my tool in my hand again as she adjusted the scant material both in front and between her ass cheeks.

The next item she picked up turned out to be a pair of black stockings rolled together. She unrolled them and started to step into one, working it up her leg. The top looked as though it had a wide band of elastic so, without seeing anything on the bed looking like a garter belt, I assumed they were thigh-highs. She pulled the second one on as I continued to stroke my tool and, standing there in thigh-highs and a thong, she still kept my dick as hard as when she'd been naked. The next item she pulled on was a push up bra that took her substantial tits and made them look as they probably had twenty years ago. Her fleshy globes practically spilled over the top and jiggled with every movement. Stepping over to her dressing table, she plugged in her hairdryer then leaned forward as she undid the towel on her head. She shook loose her long blonde hair, setting her tits to jiggling again and pushing me right up to the brink of cumming. Setting the towel aside, she started to work on her hair as I stared at her ass and the reflection of her tits. Before she'd finished with her hair, I shot my second load onto the side of the house.

I tucked myself away and continued to watch as she did her makeup and slipped into a short, tight black skirt and a white blouse. I started to wonder if she was just out with her girlfriends or was she on the prowl to get a little. I couldn't imagine that she'd bring a guy home with her, but would she go to his place or maybe fool around out in the parking lot of a bar? Or, if she didn't hook up, was she coming home and taking care of her needs herself? So many questions came to mind that I suspected I'd be doing some future voyeuring. I continued to watch as she put on some jewelry and some perfume, did a few finishing touches, then shut off her light and left the room. I moved myself into a position where I'd be able to see her get in her car and take off and as soon as she was gone, I was rapping on the back door.

Jen was there in seconds, opening it and letting me in, telling me how quick I'd been. I cut her off with a passionate kiss, reflecting how, despite relieving myself twice, I was still on fire. My hands were all over her ass and, surprisingly, I could feel the life returning to my cock once again. I picked Jen up and carried her through the house to her bedroom, where I laid her on the bed. I grabbed the waist of her pants and panties and pulled them straight down and off, revealing her pussy. I opened my jeans for the third time and pushed them and my underwear down to my knees, my cock at three quarter staff. Laying on top of Jen and feeling her warm tongue entering my mouth, I guided my cock between her lips, already slick with her flowing juices. With a slight push, I slid completely into her with a combined groan of relief and pleasure.

I immediately started fucking her hard and she immediately responded. She was crying out and raising her hips up to meet my downward thrusts, while holding me tightly. Her hot, tight pussy felt so much better wrapped around my cock than my fist had. Visions of her before the mirror, pants and panties at her knees, shirt up to her chin; her mom naked coming in the door, drying her hair in thigh-highs, thong and push up bra; and Jen lying on the bed as I pulled her pants and panties off, her legs opening up to accept me passed through my head, making my cock as rigid as steel. Jen's cries were getting louder as I fucked her harder and faster until finally she just pulled me against her and shuddered as her orgasm washed over her. I continued to fuck her and when she finally pulled away from me, she stuck her tongue in my mouth for a minute or two then told me she wanted to suck my cock.

I rose up off of her and Jen moved out from under me and off of the bed. I lay on my back on the bed, my legs hanging over the side as Jen pulled my jeans and underwear off. Before she knelt on the floor, I asked her to strip off the rest of her clothes, wanting to see her completely naked as I had her mom. Her shirt was hanging down far enough to cover her pussy, so when she pulled it up I first admired her bush again from a closer vantage point. Then her stomach and black bra came into view as she pulled the shirt over her head and let it drop to the floor. She popped open the front clasp of her bra and separated the cups, revealing the smooth, pale flesh of her tits and their pink areolas and nipples. Her nipples were hard and I looked forward to sucking on them before the night was over. Once her bra had hit the floor, Jen stood before me, allowing me to admire her, for a minute or so before dropping to her knees.

My cock was still standing straight up as she took it in one hand and lowered her mouth onto it. Her mouth felt as incredible as her pussy, but in a somewhat different way. Instead of the snug, uniform grip, I could feel her tongue sliding up the underside of my cock as her lips slipped up and down my shaft. She wasn't a bad cocksucker, bobbing her head up and down, taking me as deeply as she could manage. She seemed to be enjoying it too, having my cock sliding in and out of her mouth. She paused to lick my balls, while pumping my saliva-coated prick in her right hand. I was still seeing visions of her mom, wondering how her mouth would feel on my cock, wondering how she would taste if she was sitting on my face while Jen sucked my cock. In spite of these fantasies, and despite the fact that Jen was doing a truly fantastic job of sucking my cock, I was afraid having cum twice already that night that I wouldn't be able to cum in Jen's mouth. I didn't want her to feel as though she wasn't doing a good job, so after a few more minutes of amazing sucking, I told her I wanted to fuck her some more.

Jen reluctantly slipped my cock free of her mouth and, still pumping it in her hand, told me that she really wanted me to cum in her mouth. I promised her I would, but I wanted to feel her hot pussy some more first. I had her straddle me in the position I was already in and guided my cock to her hot pussy, having her sit down on it. She leaned forward, hanging her tits in my face, as I reached around to grab her ass and pull her down on my cock each time she rose up. While she was riding me, I put my tongue and lips to work on her tits, licking and sucking her hard nipples. She started out riding me slowly, almost cautiously as if not to make me cum, but soon was riding me hard and moaning loudly. I was enjoying her tits and continued to pull her down hard on me while pushing my rigid cock up as far as I could. It took a while, even with the visions continuing through my head and her snug, slick pussy sliding up and down me, but I finally started to feel and orgasm beginning to approach. It was still a ways off and I was enjoying the feel of it building with each pass of Jen's pussy up and down my shaft. I was very pleased when, with my orgasm still a safe distance off, Jen let out a cry and began to shudder through another orgasm. Her pussy was flooded with a fresh flow of lubricating juices, so by the time she recovered from cumming, I was on the verge myself.

I allowed myself to get as close as I dared, enjoying the feel of Jen's pussy and still sucking her nipples. Finally, I told Jen that I was about ready to give her a mouthful and she about jumped off of me onto the floor. She resumed her sucking, using only her mouth and undoubtedly getting a good taste of her own pussy. It occurred to me that I hadn't had a taste of her pussy myself and I wondered briefly whether I'd have a chance to that night. I had no doubt that I would at some point.

I felt the sap beginning to rise, thanks to Jen's oral stimulation. I muttered some words of encouragement as my cock swelled and she picked up her pace, working to bring me to orgasm. Finally, with a grunt, I started spewing my third load of the night, this time into a nice warm mouth rather than on the side of a house. Jen continued to slide her mouth up and down my cock, even while swallowing the load of cum I provided her. Even as my cock was going limp, she continued to gently nurse it.

Eventually, she let my cock slip from her mouth and stood. I moved up onto the bed and she lay beside me. Glancing at the clock, I saw that hardly any time had gone by since her mom had left, so I knew that we had plenty of time ahead of us for more messing around. I briefly considered whether I should hang around after I left Jen to see what her mom got up to after she got home, but Jen had me so satiated by the end of the night that it would have taken the promise of a lot to get me to stand out in the cold, looking through a window and waiting.

That's not to say I never went back and looked through that window again.