Voyeuring a Milf

Jen’s mom was even hotter from five feet away, on the same side of the window, and peeling off her clothes. I was sitting naked in an armchair in her living room, my rigid cock protruding from my lap like a rocket ready to blast off, just watching her. This time she knew I was watching and was doing a little striptease just for me. She peeled off her white blouse, wiggling for me in just a tight miniskirt and push-up bra before reaching for the zipper at the back of the miniskirt.

She shimmied out of the skirt, setting her boobs to jiggling atop the lacy cups of her bra, and it was soon bunched at her ankles. Standing before me in her bra and panties, she shook her titties for me some more before leaning forward while reaching for the bra clasp behind her. Suddenly the bra went slack and she let it slide down her arms, her tits now swinging freely. I was nearly hypnotized by her swaying breasts before she stood up again. I stared at her large, freckled tits topped with those big, dark aureoles, anticipating spending a lot of time that night sucking on her nipples.

My attention was drawn away from her tits as she started to work her panties down over her hips. As the black material moved down and her dark blonde curls started coming into view, I’m surprised I didn’t blow my load right at that moment. I stared, slack-jawed, as her panties hit the floor and she stood before me in all her naked glory. She smiled at my obvious appreciation before stepping toward me and dropping to her knees. My eyes got wider as I realized what she intended to do. She leaned forward to kiss my chest as her tits dragged against my hips and my cock poked her in the sternum.

She looked up and smiled at me as she took her hands and pushed her tits together around my cock. Her warm, soft, smooth flesh felt incredible as she slid her tits up and down my shaft, sticking her tongue out to lick the tip each time it appeared. Fucking her tits felt incredible, but it was nothing compared to the feeling when she opened her mouth and slid her lips down my shaft. Her warm mouth engulfed me fully to the root, where she held me as her tongue moved around the underside of my cock. She then slowly slid her lips up to the head before plunging back down, again taking my full length. Her rhythm picked up as she bobbed her head up and down repeatedly, sliding my cock in and out of her mouth.

I started raising my hips, feeling and anticipating my impending orgasm, as Jen’s mom continued to make love to my cock. Finally, I closed my eyes as I exploded in a torrent deep into her mouth. My orgasm was so intense that I almost felt as though I’d left my body. I started to feel as though I was lying down with something covering me. The feeling was so real as I continued to shoot my load that I quickly opened my eyes, only to find myself lying in my own bed spewing cum onto myself and my sheets. It had all been a dream! It had been an incredible and so completely realistic dream, but it was still extremely disappointing.

It had been several weeks since I had spied on both Jen and her mom before spending the evening fucking Jen’s brains out. Though I had fucked Jen a number of times since then, I hadn’t been back to her house. As I lay there, cum starting to dry and stick my sheets to me, I started thinking that it might be time to pay Jen’s mom’s window another visit. The question was: how?

I could easily head over there every night until I caught her again, but that would not only increase the probability of getting caught myself, but could result in a lot of boring waiting around out in the cold. How long was I willing to sit outside waiting for maybe five minutes of seeing her get undressed for bed? I could try for the same scenario as the first time, waiting for a night when she was getting ready to go out again, then utilizing my arousal for Jen’s benefit. That had a proven history, but I still wondered about the potential for more.

If Jen’s mom didn’t have a man in her life, what were the odds that I could catch her taking care of her own needs? I started to think about when she would be most likely to do this and figured it would probably be one of two times: when Jen wasn’t home or after a night out. I could determine when either opportunity might present itself simply by talking to Jen. Whichever one came up first would be the one I tried first. If both of them came up on the same night, I guessed that my odds would increase dramatically.

The next time I talked to Jen, I began to pick her brain for information relating to her mom’s habits on the premise that I wanted to come over the next time she went out for the evening. I learned that when she went out, she generally didn’t get home until very late – late meaning shortly after 2am when the bars closed, not like 5am meaning she’d probably spent the night with someone. Typically she left around the same time but Jen didn’t know if she always went to the same place. Also, there didn’t seem to be a pattern to when she went out.

Jen didn’t realize it would be good news to me when she suggested that since she’d be out of town the following weekend on a road trip with her girlfriends, her mom would probably go out then. She was lamenting a potentially lost opportunity while I was celebrating a very positive set of circumstances.

I thought through a plan for the night Jen would be gone and decided that I’d stop by around the time I’d seen her mom the first time, then come back later and try to catch her again. I surmised that it was possible she might not come home alone, but by the same token, she might not come home at all. I figured I’d better at least try to catch her before she went out in case the later opportunity didn’t come. I contemplated following her to her destination to keep tabs on her for later viewing, but decided that felt uncomfortably like stalking.

When that evening rolled around, imagine my disappointment to find Jen’s mom’s car gone and the house completely dark. I had no choice but to settle for a single potential viewing opportunity and even that wasn’t guaranteed. I have to admit I was a little distracted that night while I was out with my friends, which I claimed was due to feeling slightly under the weather. They understood when I decided to call it a night right around last call.

Instead of heading home for rest, I headed over by Jen’s house and parked where I wouldn’t be conspicuous but would be able to see her driveway. You can’t imagine the sense of relief I felt when a car turned into that driveway. I watched as Jen’s mom got out alone and entered the house through the front door, then I was off. I snuck into the backyard and waited for the bedroom light to come on. When it did, I was pleased to note that her blinds were still open, as they had been the first time. I moved up to the window and looked into the small bedroom, but it appeared to be empty, though I thought I could hear music playing. Obviously I waited, knowing she was in the house somewhere. It was just a minute or so later when she came into the room, unbuttoning her blouse and shaking her booty.

She was dressed similarly to the first time I’d watched her through the window – a tight, short black skirt and black hose, but this time her blouse was a light blue that probably had some fancy name instead of basic white. As her blouse opened further, I could see that she was also wearing a very supportive bra once again. As she removed her blouse, she was still moving to music that I could barely hear and her tits were bouncing wonderfully inside her sexy bra. She passed the mirror on her dresser as she went to the closet to toss her blouse into a basket in the bottom. Coming back, she stopped in front of the mirror and gave herself the once over, scrutinizing her face and adjusting her hair before doing a few dance moves. From my vantage point, I was seeing her ass and her reflection, though my focus was mainly on the reflection of her cleavage. My dick was hard, but I hadn’t taken it out yet.

As she danced, she started running her hands over her hips and waist before sliding them up over her bare ribs to cup her tits. The more she started rubbing her breasts, the less she was dancing until finally she was just standing in front of the mirror playing with her tits. She turned, toward the window, fortunately, tits in hand and looked over her shoulder at the reflection of her ass in the mirror. Releasing her tits, she reached back to unfasten and unzip her skirt, letting it drop to the floor. As she continued to survey her ass in the mirror, now bare but for the thong running between her cheeks, I was basically getting a direct frontal view. She looked even more scrumptious then I remembered in her skimpy lingerie and thigh-high black stockings, but I still resisted whipping out my tool, liking the direction that she seemed to be heading.

I don’t know what she decided, but I thought her ass looked good. It wasn’t tight and muscular, but it wasn’t out of control, either. I wondered if there was some way I might get my hands on it. It was worth consideration. She’d had her hands on the small of her back as she checked out her ass, but slid them down over her cheeks and started to run them up and down. She turned back to face the mirror while massaging her ass, giving herself the once-over again. She brought her hands around to cup her tits again and appeared to be rubbing her nipples through the lacy material of her bra.

When she let the straps fall off her shoulders and pulled the cups down to reveal her nipples, I was rubbing the bulge in my jeans. She toyed with her nipples while watching herself in the mirror then pulled the bra all the way down to her waist. As her big tits sagged on her chest, she spun the bra around and unfastened it, tossing it toward the open closet. She now stood before the mirror fondling her tits, wearing only her thong panties and stockings. After a few minutes of caressing her tits and gently pulling her nipples, she paused and bent over. It looked as though she was retrieving something from the bottom dresser drawer.

When she stood and turned toward the window, she was holding a dildo. I think at that moment I truly realized the meaning of “paydirt.” She passed the window without even glancing down at my location, so I adjusted my position to be able to follow her course. Tossing the dildo onto the bed as I stared at her ass, she hooked her thumbs into the sides of her panties and pushed them down. As she bent over to retrieve them from her ankles, I saw her dark blonde curls and pink lips peeking at me from between her thighs.

Slowly I began to unfasten my jeans. I continued to enjoy the view as she crawled onto the bed, thinking how I’d like to be behind her ready to slip into her undoubtedly dripping wet pussy. She propped her pillows against the headboard, then turned over and sat up against them with her legs bent and spread wide. What an inviting view! She picked up the dildo and rubbed it over each of her nipples before slipping it into her mouth. She had no trouble deep-throating the entire latex unit. I was alternating between stroking my cock and fondling my balls, expecting that I would be shooting my load long before she was done.

She withdrew the dildo from her mouth and guided the tip between her pussy lips, arching her back slightly as it penetrated her. Her mouth was open in an “o” shape but her eyes were shut as she embedded the dildo within her blonde curls. As she began to slide it back out again, I was fisting my cock, which was as rigid as a steel bar.

With two hands on the base of her toy, she began pumping it in and out while raising her hips and ass off the bed. She wasn’t going slow and sensual, she was enthusiasticly all-out fucking herself. One hand left the base of the dildo and sought out her clit, which she vigorously rubbed as she fucked herself. Despite the cold, my pants were down almost to my knees so I could fondle my balls with one hand while pumping my cock with the other. I was pushing my hips, imagining I was balls-deep in her blonde pussy instead of my hand, trying to match her frenetic movements.

As she continued to fuck herself, I released a stream of cum that felt as though it shot halfway across the backyard. I kept stroking and kept cumming without taking my eyes off of her until I was finally spent. I just stood there, my shrinking cock in hand, and watched as she reached her own climax. Her hips and hands were nearly a blur until she finally tensed up before convulsing a few times and going limp on the bed. She let her hands drop onto her stomach, leaving the dildo embedded. Her chest was rising and falling rapidly as she tried to catch her breath, her eyes still closed.

Reluctantly, I packed my flaccid cock away while keeping my eyes on her. My pants were re-zipped before she moved again, sitting up and sliding the dildo free. She half-heartedly licked it clean, looking pretty much exhausted, then dragged herself up off the bed to put it away. I watched as she turned off the music she’d been playing and walked to the door to shut off the overhead light. I waited to see if she’d turn on one of the small lamps, but she never did and I didn’t see her silhouette in the doorway. I stood around for a few more minutes before deciding that she was probably asleep, then headed for my car. My mind was already hard at work trying to figure out how to get a personal taste of that hot action.