Dog Sitter

Dog Sitter [part 1 of 5]
By: Raingirl

Hi, my name is Teri. I'm 46 years old, married to my husband Joe and have two daughters, 18 & 20 who both attend college out of state. My husband is a very motivated, type "A" who works for a machinery manufacturing company and heads up their overseas marketing. What that means is that he is out of town probably 150 days a year. It wasn't so bad while I had my daughters at home, but it gets pretty lonely now that the youngest daughter has started school in Texas.

I'm in reasonably good shape and weigh 130#, 5'5" with auburn hair and green eyes. I wouldn't say that I have an overactive sex drive, but I find myself wishing there were more intimate moments with my husband than I'm currently getting. Usually when he's been flying around the world for a week or two, it takes him 3 or 4 days to get re-acclimated to his sleeping schedule, so he's usually way too tired to "play" with me when I've got all this stored up desire.

Last year, after feeling a bit melancholy about turning 45 years old, I convinced my husband to buy me some plastic surgery and had my breasts lifted and enlarged slightly. I had been a small "B" cup and was sagging more than I liked and now I'm a firm "C" with a little more "perky" to my nipples. I was hoping the new look would reinvigorate my sex life with Joe, but after a fleeting bit of renewed interest in having sex, the same old doldrums took over our routine.

Now here I was an empty-nester in more ways than one. My girls were away at school and my husband was increasing his travel, much to my disappointment. Joe started realizing the problem and he invited me to meet him in Tokyo in between sales calls he was making. We were to have a few days of sightseeing and stay in a nice four-star hotel and get pampered with massage, dinners on the town and the whole nine yards.

It was a short notice kid of thing and I quickly went out and bought some new clothes and started packing for my little adventure. Then it suddenly struck me, what was I to do with our dog, Shep. Now Shep was a 12 year old German Sheppard who was pretty feeble and I didn't dare try to take him to a kennel for boarding. I quickly came up with a possible solution, I'd call my daughter's old boyfriend Ben and see if he would "dog-sit"

Now Ben and my oldest daughter Jill had gone out together for two years prior to her going off to college. They were still friends, but they weren't romantically involved anymore. I knew Ben was always up for earning a few extra bucks since his family was pretty strapped for money and Joe was still attending community college.

"Hi Ben this is Teri James, how are you?!" I said.

"Great Teri, what's going on with you?" Ben replied.

"Well, I'm in a bit of a bind and I wondered if you could help me out." I quickly cut to the chase.

"Sure Teri, what is it?" Ben said with an interested tone.

"I'm going out of town for five days and was wondering if you'd be able to house-sit and take care of Shep? I asked.

"Hey, I'd be glad too, just stock the fridge with pizza and I'll be there!" he said jokingly.

We set up the time for him to come over and I slipped $200 in an envelope for his trouble. Since my flight was leaving at 6:30 AM and I had to be at the airport two hours early, I suggested Ben come over about 9:00 PM the night before and just spend the night since we'd have to leave the house about 3:30 AM to make it to the airport.

Ben arrived right on time and I answered the door and gave him a big hug. "Thanks ever so much for doing this for me Ben, I really appreciate it."

It was a bit uncharacteristic, but I felt his arms circle me and give me a bit more return hug that I had ever gotten from him before. About then, Shep came lumbering up and gave Ben's hand a lick.

"Hi buddy, boy are we going to have fun together!" Ben said enthusiastically and gave Shep a quick stroke on his head.

"I went and bought food for you and Shep and here's a little extra for your trouble." I said as I handed him the envelope with the cash.

Ben quickly glanced in the envelope and retorted "Teri, this is too much, I mean I feel like a gigolo or something!"

The comment took me aback and I was surprised at the reference, but quickly dismissed it and said "It's just my way of saying thank you for helping out."

I was very disorganized and was still trying to round things up to pack and realized I had some things in the laundry to get clean and dry before I could pack them. I told Ben to sleep in Jill's room and he was free to do whatever he wanted while I packed. I was starting to get a bit nervous when it got to be 11:00 PM and I was still running around like a chicken with her head cutoff.

I was trudging up and down the stairs multiple times and was now waiting for the dryer to finish so I could finish the last few items of packing. Ben had wished me "goodnight" and retreated into Jill's room and closed the door. I went and got ready for bed and dressed in my usual short-nightie and pulled on a little robe just in case Ben reappeared from the bedroom.

I was getting to the bottom of the stairs and was just outside Jill's room when the dryer shut off. The din of the dryer left the hallway silent. It was then I heard a faint voice from inside Jill's room.

"Teri" I heard Ben say in a muffled voice.

I stepped right close to the bedroom door and heard it again "oh Teri..."

The light in the hallway was off and I quietly grasped the doorknob and twisted it open, I pushed the door ajar just an inch or so and peered inside. The window blinds were angled such that a bit of light from the streetlight outside gave a bluish glow to the room. The headboard was against the same wall as the door so as I looked in, I could see Ben lying on the bed with his head turned slightly away from the door. My mouth dropped as my eyes adjusted to the low light level and I made out Ben's naked body, but more revealing was his hand wrapped around a huge hard-on and he was slowly stroking it up and down.

I heard him make little groans and grunts and then he repeated "Oh Teri!"

"He masturbating and thinking of me!" I screamed in my head.

Now Ben is not a big gut, probably 5'9" and weighs 160#, but he's very athletic from all the soccer he plays. I marveled at the sight of his sculpted body and was amazed at how well hung he was! His cock was plenty long and thicker than my husband's cock by quite a bit. I watched in amazement as he fucked his fist and kept uttering my name.

My knees were shaking and my stomach was in knots. I started to retreat, but I couldn't. My free hand curled up under my nightie and I pressed my palm over my mound. I could hear my own heartbeat pounding in my ears as I curled my middle finger inside my slit.

I could see the droplets of precum oozing from his slit and he'd rub the slippery stuff all over the head of his cock as he continued to jack-off. Then he said "Fuck me Teri......."

I heard a teeny groan come from my own mouth and hoped he didn't hear me. I never had any idea that a 20 year old boy would be fantasizing about fucking the mother of his ex-girlfriend. All my sexual frustration from the past year or two suddenly flowed over me. I could feel myself about to climax from the sight of Ben's activity and a soft touch of my own pussy. I mustered all my courage and tried again to retreat and end this before anything got started.

"oh Teri, you feel so good inside!" he muttered.

Visions of his thick cock sliding into my lonely pussy were suddenly all I could think of. I was hooked! I knelt down and got on my hands and knees and slowly pushed the door open enough to crawl inside. His head was turned towards to window as he continued beating his cock with his open fist. I got closer and closer and marveled at the sight of his sex. My pussy was seeping juice now as I got right next to the bed. It was too late to turn back now and now my whole body yearned for his cock to be inside me.

I rose up on my knees and gently put my hand on his hip.

Ben sat up, startled and yelled "Oh shit!" as he tried to cover himself but the sheet and blanket had slipped to the floor.

"It's okay Ben, I understand!" I said in a calm voice as my hand replaced his around his throbbing cock.

"Teri , I, I...." he started to try to come up with an excuse for his condition.

I kept my eyes focused on his face as I opened my mouth wide and took the pulsating head in.

"Oh my God Teri.................." he gasped as I swirled my tongue around the swollen member.

It was alive and twitching and I could feel the blood pumping thru it like a fire hose. I crawled up on the bed and crouched over his groin as my head bobbed up and down in a steady rhythm. Ben's eyes were as big as saucers and they stayed focused on me as I got lower and lower onto his shaft and tried not to gag as his cock head jammed the back of my throat. . I wasn't very good at sucking a man's cock since my husband was never very interested in giving or getting oral sex!

I figured he wasn't going to last very long at this rate and I was getting selfish about what was going to happen next. I really wanted that beautiful cock inside my pussy and filling my womb with his hot seed. I pulled off his cock and sat back on my knees. He stared at me a little unsure what was to happen next. I pulled my nightie over my head to reveal my naked body to my new young lover.

I was never much into talking dirty or anything like that, but the moment seemed to present itself and I blurted out "I want you to Fuck me Ben, I want to feel your cum flooding my cunt!"

It was like I suddenly turned on the "overdrive" switch on his sex drive. He pulled me down onto the bed and got me onto my back. It took him just a few seconds to get positioned between my legs, spreading them wide apart, then he pinned my wrists over my head and slid forward to impale his cock into juicy slit.

"God you feel so good Ben!" I squealed as his cock took just three short thrusts before he was fully imbedded inside me. He lowered his head and began nibbling on my erect nipples as his balls slapped against my ass with each thrust. His two-day growth was rough on the tender skin of my breasts, but it was also very exciting and seemed to add to the whole atmosphere of being "taken" by my daughter's ex-boyfriend.

Now when Ben fucked you, it wasn't just sliding in and out with a nice steady rhythm, and he would thrust in so hard that my body shook and our hips would collide with such force that it bordered on painful. His strokes were so hard and fast that my breast would flop up and down with each pounding lunge.

I'd never been fucked with such force. It was a little scary at first, but I soon relished the rough treatment and begged for more. Ben was sitting up on his arms to get the best angle of penetration possible. The stimulation against my clit was intense and the first wave of my orgasm caught me off-guard. I could hear myself screaming in ecstasy as my body convulsed violently against the onslaught of Ben's fucking.

"Oh god Ben! Oh God! Oh God!" I kept chanting.

The sound of wet sex was filling the room and sweat was pouring off Ben's face as his teeth clenched and his hips pummeled into me. It was so overwhelming that my climax continued to build and get even more violent as Ben continued fucking me. It was a level of sexual satisfaction I never knew existed! I wrapped my legs around him and gave him even better penetration to my pussy.

Somewhere in the blur of the moment, Ben let out a groan and powered into my pussy once more. I could actually feel each squirt of his powerful stream hitting inside my vagina. He collapsed onto me, but kept fucking me with slightly less vigor. My pussy was awash with juices and cum. I never had felt such a wonderful feeling inside me. We were both panting like crazy and the coating of our sweat between our bodies caused a delicious lubrication between us.

His mouth covered mine and we kissed. This was the most voracious and emotional kiss that I'd ever experienced. Our tongues were like a couple of dueling swords and his mouth was all over my face, my eyes, my ears and up and down the length of my neck.

His hands continued to fondle all over my body. My pussy was still stuffed with his cock and my body was still jolting periodically with the remnants of my orgasm. After a while, He rolled off to the side of me and I could see the reflection of the street light glisten over my sweat covered body. I rolled to my side, facing away from him, and I was starting to have these deep guilt pains. I felt him snuggle up to my backside and his arms wrapped around me. His fingers found my nipples and he gently caressed them as his lips trailed along the back of my neck.

My mind was a flood of mixed emotions! I'd just cheated on my husband of 23 years and I was really feeling guilty about Not feeling guilty! I'd been needing attention and my husband wasn't giving it to me, so I reasoned that this was okay! Then I thought about my daughter Jill and what she would think if she knew. I tried to recall the things she said about Ben when they broke up and I again figured that the two of them had moved on from each other, so it was alright for me to take him for my love toy!

I was startled back to the present as I felt Ben's cock burrowing into the crack of my ass and I could feel that he was rock hard once again. The remains of our juices that clung to his shaft along with my own perspiration made a nice bit of lubrication as he rocked his cock into the cleavage of my ass. Now I came to another revelation, he was working his way lower so the tip of his cock was getting dangerously close to my asshole!

Now Joe and I had never had anal sex, in fact, we'd both considered it rather vulgar and filthy. We had been in a similar position where Joe had stroked his cock between my cheeks just like he would occasionally fuck my tits, but I had never contemplated it actually happening to me.

I turned my head over my shoulder and said "No Ben, we can't do that."

"So you've never done this before, have you?" Ben said as he kissed the side of my neck and making me swoon a bit.

"No, I haven't." I admitted.

"Although I have a friend who said she's tried it and really enjoys it." I blurted out and flashed back to a conversation I had with my old friend Jane just a few weeks before.

I started wondering about that admission she told me over a couple glasses of wine and I started to wonder now if she and her husband of 18 years suddenly started experimenting with new things in the bedroom. Her husband was probably worse than mine as far as being a work-a-holic and suddenly I wondered if her admission about trying anal sex was also an admission that she was having an affair?

As Ben continued fondling my breasts and nipples and I could feel his slick cock sliding up and down along the crack of my ass I said "I wonder how she got started with something like that?"

Then Ben whispered into my ear "That wouldn't be Jane Stubbs your talking about?"

Bells went off in my head and the two things clicked. "It was you!" I said with a mixture of horror, jealousy and wonderment.

"Yes it was me." Ben said. "Jane was feeling very alone and neglected and when I was doing some pruning on her hedge in the back yard, she invited me in for a drink and........ well, things started to happen!"

My heart was pounding even harder now realizing that Ben had been sleeping with one of my oldest friends!

"How long have you two.........?" I asked rather sheepishly.

"Just a few times." Ben said as his fingers rolled the erect nubs of my nipples and pulled them slightly. "I like making love to a M.I.L.F."

"What's a M.I.L.F.?"

"Mother Id Like to Fuck!" Ben smiled.

The image of Jane being ass-fucked by Ben was suddenly all I could see in my mind. Jane was a very stylish woman with great legs and a beautiful body and I was imagining her getting slammed just as I just had been. I started to feel like some sort of housewife slut, trolling for some young stud to service me. The thought of the whole thing made me even more sexually heightened and I wanted to be Ben's fuck toy.

It took me just a few seconds more to conclude in my head how to proceed from here. I turned back to Ben and said in a soft sexy voice "I want you to ass-fuck me too!"

I think Ben had already figured that was going to be the next step and he reached over to the nightstand where there was a tub of heavy hand cream. He got me onto my hands and knees and took a liberal amount of the thick paste and began smearing it around the entrance to my ass. I felt him spit a large dollop of saliva right onto my sphincter and began working that together with the heavy hand cream and it seemed to turn into a very slick liquid that he started working into my asshole with his finger.

"Ohhhhhhhh" I gasped as his finger slid part way into my ass and I dropped my shoulders to the bed. He continued getting more of the lubrication on his finger and worked it deeper and deeper into my virgin hole. He pressed into about his second knuckle and wiggled it around a bit that sent shivers through my body.

"Just relax Teri, I'm going to take plenty of time to get you all loosened up before you get the real thing." Ben said calmly as he thrust and rotated his middle finger around in my ass.

Ben took his other hand and reached underneath to fondle and finger my dripping wet slit. I groaned again at the sensation of him having two fingers in my pussy and another sliding deep into my ass. After a couple minutes of this double penetration, I was cumming again!

As wave after wave of these amazing sensations flowed over my body, I started wondering what else I'd been missing all these years! I felt my hips undulating and thrusting against Ben's probing and prodding as my orgasm went on and on and on. I even began pinching my own nipples as my ass waived high off the bed for Ben's pleasure.

It was as if I was in this really bizarre dream and I was fulfilling all these sexual fantasies I never knew I had until tonight. Ben was making me feel wildly different than I had ever felt in bed with a man before. I knew then that this wouldn't be my last indiscretion!

I could look back and see Ben getting in behind me and he smeared the concoction of hand cream, saliva and cum from my pussy all over the length of his cock. When he scooted forward and pressed the head of his cock against my ass hole, it felt like someone was trying to shove a broom handle through a straw!

"Oh God Ben, this is not going to work! You're too big!" I gasped in protest.

Ben didn't reply, he just kept alternating between shoving his well lubricated finger into my ass, then trying to press his cock head there. After 8 or 9 tries, I could actually feel his cock just barely penetrate my ass and it was like firecrackers were going off inside me. There was pain and I was scared as hell, but there was also this amazing realization that he actually was going to get his fat cock inside my virgin ass and it was super erotic and exciting.

Ben was slow and gentle as he could be and it probably took a good ten minutes before my sphincter finally relaxed enough for him to shove about half his length inside my ass. Then Ben said "Slide a couple fingers inside your pussy Teri and feel my cock thru the wall!"

I was again in shock. He was suggesting fingering my own pussy and feel his cock that was sliding in and out of my ass. Without anymore thought, I did it. My pussy was dripping with the mixture of my and Ben's cum and it felt really slutty for me to be shoving my own fingers inside my own pussy filled with that sexy goo.

Sure enough, I could feel the head of his cock thru the wall membrane as it glided into my ass. I tried giving it a little tickle as Ben kept stroking deeper and deeper with each stroke. My own knuckles were pressing against my swollen clit as I tried to shove a third finger inside my pussy and play with his cock. My body began shaking again with another orgasm and I was grinding my own knuckles over my clit like crazy.

I glanced back at Ben who was diligently trying to get his entire cock buried inside my ass. He could feel my fingers against his cock and smiled. His strokes were long and deep now and his nut sack would touch my hand now every time he slid into my ass fully. I couldn't believe how the feeling of his cock in my ass had turned from pain to sheer pleasure! I loved the way it filled me up and I was relishing every stroke.

We fucked like that for a long time. Not much was spoken, we just moved against each other's bodies and listened to the sounds of slick squish sex. I knew now that I was hooked on being ass-fucked. I know too what Jane felt like and how come she was raving to me about it. I closed my eyes and pictured Jane in my position and having Ben fucking her tight hole.

I was really enjoying the pace of Ben's fucking and the pressure it put on my womb. I noticed that Ben's strokes started getting a little more forceful and a little faster than before. I was excited to think he was getting ready to blow another load of his cum inside me, and this time in my Ass! I started rocking harder back against his thrusts and slipped my fingers from my pussy so I could play with his balls. That seemed to be just enough extra stimulus to send him over the edge. He grabbed my hips and yanked me back towards him once more and then I felt the torrent of steamy hot cum pumping into my ass like someone was squirting a turkey baster.

"Oh Ben that feels fantastic!" I squealed as his cock twitched and throbbed and pumped stream after stream of cum in my ass. The extra lubrication of his cum now made the canal nice and slippery as he continued pumping in and out of my hole.

We finally collapsed into each other's arms and before long, we were both asleep. I woke up a while later and started to panic! What time was it? We had to leave for the airport by 3:30! I glanced at the clock, it was 3:05! I flew from the bed and headed upstairs to shower and dress. I was in the shower and started to relive the past few hours with Ben. My hand took the bar of soap and ran it up and down my pussy slit and also around the entrance to my ass. Wow it was sore, and I could even slip a finger inside there which I never could do before.

I finished showering and got myself dried off when Ben came into the room, dressed and ready. I was trying to dash past him to get my clothes on and he grabbed me and pinned my against the wall and kissed me hard. Part of me was struggling to get past him, but the other part of me want to jump back in the sack with him.

"Ben, I've got to get dressed, now let me go!" I said in a half serious, half kidding way.

I finished putting the last few things in the suitcase and sent Ben to put in in the car. As I put on my underwear, I could feel my pussy and ass still oozing cum. I quickly grabbed a panty liner and stuck it on my panties and finished getting dressed. Amazingly enough, we were backing out of the driveway right at 3:30 AM.

The ride was quiet for a couple minutes and I starred at my young lover as he drove the car onto the interstate towards the airport. We were still 40 minutes from the airport and I was already missing having Ben's cock inside me. I slid next to him on the front seat like I did when I had a crush on a boy in high school. Ben quickly dropped his hand to my thigh and rubbed up under the hem of my skirt along my thigh until he was fingering my slit through my panties.

"God you know how to get me going lover!" I said.

I decided to reciprocate and began fondling his cock thru his jeans. After a few minutes of this mutual fondling, Ben said "Unzip my jeans."

I smiled at him and could think of nothing I'd like better. I opened his jeans and found he was not wearing under-shorts and his cock sprang from the opening. I scooted over and laid my head in his lap and took his cock into my mouth. I could taste the strange mixture of sex juices still on his skin and I eagerly sucked his cock harder and deeper into my mouth. I couldn't believe that me, a mother and faithful wife as o few hours ago was now a dirty little M.I.L.F. and I was dutifully giving my new lover a blow job while driving down the freeway.

The ride was coming to an end and I sucked him hard and fondled his balls to get him to cum. Sure enough, he thrust into my mouth and I felt the squirts of his jism filling my mouth. I had barely gotten sat up and got his jeans zipped up when we arrived at the airport. He got out and put my bag to the curb. I turned to him and he took me in his arms.

"Have a nice trip." He said. Then he kissed me with the flavor of his seed still fresh in my mouth.

The whole trip over to meet Joe, all I could think about was getting home to my new sex toy!