Chip's Mom

I had just arrived home on break from college and was in Chip’s neighborhood, so I figured I’d just drop in and see if he’d gotten home yet. No one answered when I rang the doorbell and I was about to head back down the driveway when I heard a splash, indicating that someone was using the pool. I walked around the side of the house thinking it might be Chip but stopped before I opened the gate to the backyard. I could see the diving board still vibrating and a figure just surfacing at the shallow end of the pool. It wasn’t Chip or his sister or even his dad exercising visitation rights with his former home and it actually took a minute to register who it was. It was Chip’s mom.

I’d known Chip for as long as I can remember and even during our hormone laden adolescent years I’d never thought of his mom as anything more than a mom. As she climbed the steps out of the pool, though, dripping wet in a pretty small red bikini, reminding me of Phoebe Cates in “Fast Times at Ridgemont High,” that all suddenly changed. Of course she was no Phoebe Cates, but she still looked so damn fine that I wondered how I had never noticed her figure before. Her nipples were pressing out obviously against the top covering her moderately sized breasts, her stomach was flat and smooth and her legs, though not long, were slim and shapely.

As I stood in the shadows by the gate watching her walk over to a chaise lounge, I also realized that her ass was pretty damn incredible. I could feel a rise in my shorts but couldn’t tear myself away to go home and take care of it. She dried off, rubbing that lucky towel up and down her legs and across her stomach, then spread it out on the chair and lay on top of it.

I watched for a few more minutes and was just thinking about slipping quietly away when she did something that glued me to where I stood. Her nipples were still standing at attention, never having gone down since she exited the pool, and one of her hands slowly came up and began to gently tug on one of them. My dick was instantly rock hard again. Her eyes were still closed, but mine were open wide enough for the both of us. Her other hand came up and played with the other nipple and before I knew it she had pulled her top down, exposing her milky white breasts to the sun. Her aureola were about half-dollar sized and her nipples were pretty long and fat. She was running her hands all over her breasts now, brushing her palms over her nipples and tracing circles around her aureola while occasionally pulling or pinching her nipples.

My cock was already struggling to break through the front of my shorts, but when her right hand dropped between her legs and her fingers moved up and down over the front of her swimsuit, I thought it would explode right there. She pulled her feet up to her ass and pressed their soles together, spreading her knees apart. When her hand slid into the bikini bottom, I pulled my dick out and started pumping away. Her left hand was alternating from one breast to the other, still teasing her nipples, and her right was sliding up and down her slit from the looks of the movement inside her swimsuit bottom. She must not have been worried about anyone coming home because she paused briefly to pull the bottom of her swimsuit off, dropping it on the ground next to her. Seeing her neatly groomed light brown bush framed by the white flesh within her tan lines, I was already on the verge of cumming. She went to work on her pussy with both hands, plunging two fingers into herself as the other hand vigorously rubbed her clit. Her eyes were tightly closed and her mouth hung open while she raised her hips against her ministrations, but she never made a sound. I forced myself to bite back any noises as well when a torrent of cum suddenly shot from my rigid tool accompanied by a feeling of pleasure like I have rarely experienced before, certainly never before by myself.

When I blinked the stars from my eyes and was able to see clearly again, still holding my softening cock, I watched as Chip’s mom’s movements reached a frenzy before she froze and let a small noise slip, sort of an “oh” of pleasant surprise. She gradually settled back onto her chaise lounge and pretty soon had her swimsuit back on again, positioning herself for some sunbathing. I tucked myself away and watched for a while longer, finally convincing myself there was nothing else to see and there certainly wouldn’t be anything near what I’d just seen. I slipped quietly away and drove home, still thinking hard about what I’d witnessed.

Two things in particular occurred to me: one was that she may have started working out after the divorce, which would explain her tight body. I just couldn’t accept that I’d known her so long and never noticed it in all those years. Also, as far as I knew she wasn’t involved with anyone, though Chip wouldn’t necessarily have told me if she was, but she clearly still had needs. I had to figure out a way to put myself in a position to fill those needs. I wondered what she would have done had I just walked through the gate and offered to eat her pussy. She’d probably have darted into the house before I’d made it all the way through the gate, but who knows? Truth was, I was so shocked by what I was seeing that I never even considered getting involved. Thinking about it got me completely worked up and I wound up locking my bedroom door and jerking off again.

I decided that maybe I could try to find out just how horny she was or whether she was actually getting any. Their house was a ranch style with enough property around it that it was fathomable that they weren’t really concerned about having their shades drawn at night despite everything being on ground level. I couldn’t recall anyone going to any particular trouble to close all the blinds on nights when I was over there. Would it be wrong for me to spy on Chip’s mom if it resulted in mutual pleasure? Would the end justify the means? Would I be technically “stalking” her?

Whatever the answer to those questions, I didn’t think anything could keep me from following the plan through once I’d developed it. It was easy enough, after night had fallen, stash my car a block or so away and slip into their yard, find a window that allowed me to see into her bedroom and wait. I hung out with Chip over at his house with the intention of getting an idea of what her evening schedule was like, but when it looked like she was ready to turn in, I made an excuse myself and pretended to head home. I stashed the car, cut through some yards and made for one of her windows. There was a light on but I didn’t see her and her bathroom light was out, so I just waited. From my vantage point, I was looking sideways at her bed and could also see into her bathroom. I didn’t expect that I’d miss anything unless she decided to close the blinds. It was only a few minutes before she came in and I assumed she’d still been talking to Chip.

She was wearing long khaki shorts with a t-shirt tucked into them. I’d tried to nonchalantly check her out during the course of the evening and, while I could see how I’d missed her figure because of how she dressed, now that I knew about it, I could also appreciate it even in her conservative attire. She closed her door and I thought even locked it before turning and pulling her shirt out of her waistband and up over her head.

My heart was pounding and I was already getting stiff as her bra was exposed. She tossed her shirt into a hamper then quickly removed her bra and tossed it in as well. I stared at her beauties again as she pulled the belt out of her shorts and crossed the room to hang it inside the closet, her breasts bouncing as she walked. I noted that her nipples were hard again. She checked all of her pockets, then undid her shorts and let them drop to the floor. I was pleasantly surprised that under her mom-like shorts, she was wearing white thong panties. When she bent over to pick up her shorts and aimed her sweet ass right at me, I about creamed.

I fought the urge to whip my cock out, thinking it was too soon, and was ultimately rewarded for my patience. She dropped the shorts into the hamper and reached back to run both hands over her ass, then back around to cup her breasts and tweak her nipples. She quickly pushed off her thong but had turned her ass away from me when she picked it up so I missed seeing her pussy peeking out from between her legs as she bent over. I got a nice full frontal, though, as she crossed to the near side of her bed and dug way back in the nightstand drawer. Out came a flesh-colored, veiny looking dildo. Jackpot!

She climbed onto the bed on her knees, but set the dildo aside initially. She played with her boobs some more and slipped a hand down between her legs. In profile I couldn’t tell exactly what she was up to, but it really didn’t matter. Her hands were up and down her sides, over her boobs, between her legs and over her ass. When she picked up the dildo, she raised herself up slightly, held it under her and lowered herself onto it. She then began to ride it like she was straddling a guy, first bouncing up and down, causing my eyes to lock on her bouncing boobs, then forward and back as she leaned forward on one arm, setting her boobs to swinging.

I finally couldn’t take it anymore and released my cock and immediately gripped it and started stroking. She pulled away the arm that was supporting her and went face down on the bed, her face turned away from me and her ass up in the air. She was pumping the dildo in and out from behind as her other hand appeared to be rubbing her clit. I backed up just slightly as she turned her head toward me, but her eyes were closed and she had a look of raw passion on her face. Between that, the curve of her ass and the dildo disappearing below it and her breasts hanging against the bedspread, I was done. I shot my load into the landscaping, again stifling a groan of intense pleasure. She peaked just after I did, her movements increasing in tempo then suddenly ceasing as a shudder racked her body. She then went flat on the bed, dildo still embedded and lay there, still, for a few moments while I looked on.

I had tucked myself back into my shorts by the time she recovered, removed her dildo and stumbled off the bed. She went into her bathroom and I saw her rinse her dildo in the sink and dry it on the hand towel. She then grabbed something from the back of the door that turned out to be her nightgown, which she pulled over her head, covering her awesome body. I continued to watch as she turned down the bed, crawled into it and turned out the light. I went home, masturbated again and slept.

Based on what I’d seen in the past two days, I came to the rash conclusion that Chip’s mom was horny but didn’t have another outlet for it. Since I hadn’t come up with how to nominate myself for the position, I decided I’d just keep watching until I did to make sure she didn’t have a boy toy who just happened to be out of town this week.

The third night, I was out with Chip and though she was on my mind, there just wasn’t any way I could excuse myself without it being awkward and suspicious. When we finally decided to call it a night, I dropped Chip off and drove around the block to ditch my car. I quickly and quietly made my way to her window and cautiously peeked in. She was already in her nightgown in bed propped up on her pillows with a paperback in her hand. Chip was in the doorway talking to her, so I carefully made sure I wasn’t in his line of sight. I kept watching as he left and she put her book away and turned out the light. If anything had happened, I’d missed it. I went home and masturbated thinking about her anyway.

The next evening, Chip and I were trying to decide what to do when his mom (her name is Ellen, by the way) came in and said she was headed to the mall to go shopping. I gave her a bunch of good natured grief about how she was never going to get anywhere in life always hanging out at the mall and she’d better darn well be home by curfew. She laughed and called me “Dad” and said not to worry, she knew it was a “school night” and she’d be in home and in bed same as always. This gave me an indication that her weeknight schedule was pretty regular and gave me three more nights including tonight to verify it.

Since she was out, Chip and I just hung out at his house that night so we were still there when she got home, shopping bags in hand. I excused myself just slightly before I expected her to call it a night, again not wanting to look suspicious. I followed my previous routine, making sure not to leave my car in the same spot twice, and found myself waiting at her window again. There was a lamp on and her bags were strewn on her bed, but it was a few minutes before she came in. I watched closely this time and I am certain she locked the door this time. I took this as a good sign.

Tonight she was wearing blue shorts and a white sleeveless blouse. She began unpacking her purchases – a couple of dresses, some shorts and blouses and a few smaller packages. She laid them all out on the bed then began to undress. The blouse was unbuttoned and tossed into the hamper first, followed by the shorts. I was pleased to note that she was again wearing thong panties, which she kept on along with her white bra while she pulled the first dress over her head.

I was already hard from watching her undress and seeing her tight body again and the excitement wasn’t dampened by her covering up again so quickly. She adjusted the dress slightly, looked herself over in the mirror then pulled it over her head again. She did the same with the other dress, blouses and shorts she had bought until only the small packages were left. She looked at them sitting on the bed, then reached back and unhooked her bra. She shook it down her arms, causing her breasts to jiggle and forcing me to suppress a moan, then tossed it into the hamper. It was followed by her thong panties, though this time I did get a nice peek at her fur covered lips as she bent over.

She looked through a couple of the bags, pulled out a red g-string and stepped into it. She adjusted the strip in the front to cover her bush and pulled the string snuggly between her sweet cheeks. She looked herself over in the mirror then pulled a red bra from another bag and put it on. It was a push up bra, basically supporting her boobs, making them look bigger, but not coming close to covering her aureola and erect nipples. God, she looked hot! Again, she looked herself over and rubbed her nipples a few times before sitting on the edge of the bed and pulling out the rest of her purchase. She pulled on a pair of red, thigh-high stockings and stood to wrap a garter belt around her waist. She clipped the garters to the stocking tops and stood before the mirror. She was incredible and I was stiff, but I couldn’t help but wonder whether she had bought that for herself or to share with someone else.

As she stood before the mirror looking herself over, she was running her hands over her bare ass cheeks, across her stomach and up to her protruding nipples. I got a feeling as to where this was leading so I pulled out my rigid cock. I didn’t start stroking yet, figuring I’d wait until she did. She started by rubbing the front of her new g-string, then pulled the string up between her lips and against her clit, moving the string side to side over it. I had my cock in my fist as she backed up and sat on the edge of the bed, watching herself in the mirror as she played with both her pussy and her tits.

She pulled the front of the g-string aside and pushed a couple of fingers up into her pussy while stroking her clit. I was fisting my cock right along with her when she stopped, dashed over to the nightstand to grab her dildo, then returned to her spot before the mirror. She slipped the latex cock in and out of her mouth a couple of times, then over her nipples before bringing it down to her pussy. She pulled the g-string aside again and pushed the dildo into her pussy with both hands. Mainly looking down, but occasionally glancing up at her reflection, she pumped the toy cock in and out, slowly at first but at an ever increasing pace.

I was approaching another blissful orgasm thanks to her as I stared at her satisfying her basic carnal needs. She laid back on the bed, still pumping with both hands and now raising her hips up to meet her thrusts, her hard nipples pointing at the ceiling. I leaned against the house to support myself as I was overcome by orgasmic ecstasy, shooting load after load once again. She reached her own orgasm with a shudder and melted on the bed. I was just starting to tuck limp cock away when she stirred. She removed the dildo from her pussy and set it aside while she peeled off her new lingerie. She then grabbed her dildo and rinsed it off in the bathroom before pulling on her nightgown. She moved all of her purchases aside, turned down the bed and went to sleep. I went home and did the same.

The following day, Chip told me that his dad was taking him and his sister on a trip over the weekend and they’d be heading out Friday afternoon. He gave me the details of the trip, where they were going and what they’d be doing, then I asked about his mom, since it sounded like she was going to be stuck home alone. He told me he got the impression she liked the time alone after spending so many years with his dad, him and his sister always around. I tended to agree, picturing her strutting around the house in her sexy new red lingerie and fucking herself silly with her dildo in every room.

I had to stop or I’d pitch a tent right in front of my bud. I started thinking real hard about how to make this weekend work for me, though. I think the idea I ultimately developed came from my initial thought about her being left behind. I knew that she’d done a lot for all of them over the years and wondered when was the last time, other than Mother’s Day or her birthday, someone had surprised her and treated her like a queen. What if, after Chip and his sister were gone, I slipped into the house, made a great dinner, being extremely careful to make sure it didn’t look like I was trying to seduce her, and just sprung it on her? She might be grateful, she might be appreciative, she might think I’m a swell guy...it could potentially lead to something, if I didn’t try to hard and just let her take the lead.

I needed to work out some of the details, but unless I came up with something completely foolproof, this was going to be Plan A. Over the next couple of days, I casually picked Chip’s brain for details: when he’d be gone, when he’d be back, what time his mom got home from work. I planned a nice meal, not just a pot of spaghetti and a sink full of dirty dishes. I went fancy with the food and managed to get my brother to buy a bottle of good wine when I told him it was to impress a girl. Also during those two days, I visited Ellen’s window on both nights and was treated again to her apparently nightly romp with her dildo. I was certain she was horny now and it made me feel even more confident in my plan.

Friday finally arrived and I stopped by to see Chip at work since I hadn’t started my summer job yet. Being the nice guy I offered to run back to his house to pick up anything he might have forgotten so I didn’t have to worry about him finding me over there cooking in his kitchen. There wasn’t anything and he planned to be out of town by no later than 3pm. I said goodbye and headed to the supermarket to pick up the last of my supplies. I didn’t park in front of the house in case for some reason Chip drove past. I lugged my bags down the street and up to the front door.

Knowing Chip as long as I have, I knew where his spare key was hidden and I knew the security code for the alarm. I let myself in without any problem and the first thing I did was write a short note to Ellen to warn her that I was there and why and taped it on the door between the garage and the house. Last thing I needed was her coming home, smelling or hearing something out of the ordinary and calling the police or, even worse, calling Chip to come home. Before I dove into the cooking, I first needed to do something in her bedroom. I opened her hamper and found the thong I’d seen her strip off the night before and held it up to my nose. I inhaled her pungent, musky scent a few times and, finding myself erect, figured I’d better quit and get to work.