Double Trouble?

Nobody likes being shoved out the door….at least I sure in my mid 50s…job opportunities dried up and when I tried to make a job change…I found myself instead left out in the cold…like so many before me.

So what does a retired Math teacher do to keep from going stark raving nuts?

For the first few months I looked for meaningful part time tried a bunch of different things but finally lowerd my lofty sighjts and settled for part time retail working at Home Depot. It's okay, and I do know a lot about carpentry, painting, ect.…and does have some fringe with employee I stick with it. Usually I work one or two days during the week…not too demanding and the extra income is good although financially, I'm pretty well set.

One day as I was driving home after a day at the DIY Palace as I call it…I saw a new “For Sale” sign on the empty house next door to my place and decided to stop and check it out. The place is not exactly next is a patch of woods and a small creek that separates it from my house. The grass had gotten about waist high…much to the chagrin of the as I suspected the house turned out to be a foreclosed property.

It was one of the smaller houses in the on a nice lot with big trees…and after peering in the windows for a bit…I decided that I would look into making an offer on it. It needed some work and paint…but I have good handy man skills and through my job access to building materials and paint at attractive prices. I figured what the hell…a little more income from a rental property would be a good thing….and I had some cash to work />
Long story short…I put in a bid with HUD…and after waiting for weeks…got the house for about half its value.

Score one for the old fart…..

As soon as the loan closed I started to the the overgrown shrubs and attending to the many neglected maintenance issues that accumulate over time. The work was hot and sweaty…but was visible and directly related to effort expended, which is a far cry from teaching.

Did I mention I am an ass man? I am, very much so. I love looking at them…and most of them! really into anal…when I get the chance anyway. I think my interest in asses is a result in seeing so many cute ones wiggling up and down the halls of the high school where I taught. God….some of those girls could, and probably would, make a dead man cum. Many thanks to the Mick and the Stones for that last line.

It’s not like I don’t like tits…or sexy legs….but what does it for me. One of the few benefits to working retail is that you do see some really nice ones strolling down the aisles. Occasionally you even get a chance to rub against those things down from the high shelves, like a good customer service specialist. Every now and then…one pushes back…and that’s another story. A time or two it’s lead directly to an in home service call to render further Usually they are older women, but every now and then a little likes the way I smile….or />
Back to my newest job, renovating my rental house. Days turned into weeks and the house was nearing a state that I was planning to start advertising it for rent at the first of the coming month…a couple of weeks away. I was just finishing painting the last of the exterior and my HVAC contractor had just finished install a new heat pump, which would make the interior painting much more comfortable. Summers in Tennessee can be hot and this one has been.

I was making the very short drive from my house to my new rental house, rolling slowly down the street in my old back to the house after lunch…when I damn near drove off the road into the neighbor’s manicured yard. I had to jab the brakes hard to regain control and avoid a difficult to explain accident, but I />
What caused this sudden inability to drive at 20 mph you ask? Simple, an unexpected vision of of them older and one obviously no more than 13 or 14, standing in my yard. Both of them very, very from the back. The best part was that my first view of them was with them standing on tiptoe peering into my soon to be rental house.

Based on my observations over the a great ass posed perfectly is a rare two at the same of! But there they were, standing on their toes, legs flexed, butts taut and straining the fabric of their shorts. I had one of those “Fred Sanford” I was sure that I was having “the big one” as my heart began pounding like a jack hammer.

As I rolled into the both turned to see who had arrived, flashing very bright if slightly reserved smiles and revealing other charms that I was also lucky enough to savor visually. Both the women, or rather the woman and the young girl, were classic “girl next door” types. Glowing complexions, flashing blue eyes, and golden tans competed the picture and made me almost drool. After partially reining in my lecherous thoughts, I got out of my truck with a big grin on my face, said hello…and introduced myself.

Doug…what can I do for you ladies this afternoon?”

The older of the her hand “I’m Ellen and this is my daughter Jennifer.” “Do you by any chance know who owns this house?”

“Yes I do”. I smiled broadly, “as it happens I’m the new owner. I just bought it about 2 months ago and I’m getting ready to rent it next month…if you’re in the market.”

“We are.” Said Ellen.

My heart soared.

“But we just can’t wait ‘til next month, darn it!”

My heart crashed to the ground.

“Is there anything we can do to speed things up” asked Ellen, her ice blue eyes pleading silently? We just love this location and the house is so cute!”

got to paint the whole house inside…and do some minor plumbing />
Jennifer, bouncing up and down, gushed can />
Ellen looked at me we really need a place by the weekend…is there any chance we can paint and maybe work off some of the rent?”

can at least talk about it….want to look inside?”

Both of the charming ladies nodded eagerly and Jennifer grabbed my arm, “this is so cool…I love this it’s near my school too.”

“Oh, do you go to McKinley High” I asked?

“I’ll be a freshman this year and I am sooo />
“You do well in Math”?

“Pretty good…I hope”!

“Well if you ever need help, I used to teach Math at McKinley, so don’t hesitate to ask for help” I said as I lead her and her mom to the side door and unlocked it.

“Go on in look not a big house but it should be I followed them Ellen’s ass in encased in her tight at the obvious tone and after having one child that I knew of. Her visible skin was waist was narrow…and her chest, while not huge, was proportional to her body…if not a little more. But her ass….good god! In short…a walking wet dream…for me at least.

Jennifer, on the other hand was just beginning to develop…I could see her potential and her ass was perfect already just a little smaller than her bubble filling out her shorts perfectly. Her waist was narrow and although her breasts appeared to be were very obvious.

Now I don’t usually dwell too much on teen aged in the classroom probably forced me to not go there mentally. However, as I was learning, real life is not the classroom and I could look and perhaps even touch if the situation was right.

Meanwhile, back to the lovely Ellen who I learned was finalizing her divorce at the age of 34 and trying to be a good mom to Jennifer. We talked for a good while longer and agreed that she and Jennifer would be my first tenants. In return for their help painting and finishing cleaning the house inside, I would not charge them any rent for this month…and waive half the usual deposit of one month’s rent.

Our conversation revealed that she had kicked her husband out a few months which he drained their bank accounts, filed bankruptcy and left town. Eventually she fell behind on her sizeable mortgage and was foreclosed upon…and was being evicted the following week.

Okay…so I’m a soft touch…but damn…she was such a so damn sexy without trying to be, so…how could an old letch like me resist? Ellen was young enough to be my that didn’t mean I couldn’t fuck her if I got a chance.

We exchanged cell phone numbers and email addresses and the girls left happy after arranging to meet me at 8:00 in the morning. After they left I could not get their images out of my mind and I began to fantasize about Ellen…and too. Somehow I finished up with my outside painting without falling of the ladder while daydreaming. Then it was off to Home Depot for a bunch of paint and rollers. On the way I called Ellen and asked if she wanted any special color in her or Jennifer’s bedrooms. She giggled happily and gave me some very specific ideas, and thanked me for being so nice and thoughtful.

I told her it was my policy to try to make sure my customers at the store were satisfied so it made sense to do the same for my tenants. Yes, the play on words was intentional. Ellen’s totally unexpected reply, that she was “sure she would be well satisfied”, made my head spin.

The next week was hectic but lots of fun. Plus, I got to know the girls better and Jennifer and I struck up a close friendship. She was practically clinging to me whenever we stopped work to rest and seemed totally thrilled whenever I taught her how to paint or do anything else for that matter. Ellen kept looking at me and grinning and finally, when Jennifer went to pee she whispered: “she has a major crush on you, you know.”

“I know she likes me but a crush?”

Ellen just nodded and smiled. “Her Dad never showed her much affection or paid much attention to her unless he wanted her to do something for him.” “He was more interested in being out with “the so he claimed.” “She loves attention from men….but then…so does her mother.”

I swallowed hard. Was Ellen flirting with me?

/>
but then…..

“Well, he was twice a fool then to neglect and mistreat a gorgeous woman like you and not love and spend time with his beautiful daughter.” “He must be a compete />
“He was and is, in more ways than I can explain” Ellen sighed.

“I’ll say” chimed in Jennifer returning from the bathroom. She walked up to me…looked me in the eyes with her huge baby blues and said “I already like you much better,” and then she kissed me on the cheek.

“So do I” said her mom gently pushing Jennifer to the side, fixing me with an almost identical look and then gave me a soft kiss on the lips.

Did I mention I can still get a hard on like… instantly?

“Hey I saw him first,” squealed between her mother and me and snuggling against my broad chest.

I guess I should tell you that I’m a pretty big and about 260…blue eyes and salt and pepper hair. Most of my friends know me as mostly because an old girl friend referred to me as her big teddy bear. It stuck…but thankfully not the part.

“Okay now girls….no fighting over the landlord, there’s plenty for both of you.” I wrapped my arms around them and we had our first group hug. Yeah…I took off to fantasy land for a brief visit. Later that night alone in my bed the visit was much longer and explosively satisfying.

By Friday we had things pretty much wrapped up so I announced to the girls that they could start moving in the following morning, but I thought we deserved a treat after a hard week’s work and that I was taking them out to dinner at a nice place just a few blocks from the house.

“Can we dress up,” pleaded Jennifer?

“I wouldn’t have it any other let’s not get too carried not sure I could take both of you dressed up and even more beautiful than you are”.

I picked them up at their soon-to- be former home at 8:00. Jesus… did they look great! I knew this was going to be a very exciting evening with “the girls”.

It was.

First, I have to say I am still amazed how a woman can go from attractive and sexy to drop dead gorgeous and totally sensual with just a shower, a bit of make-up and some tasteful clothes. Ellen was simply in a clingy burgundy crepe dress that accentuated every curve of her body. The plunging neck line of her dress combined with one of those bras that “lift and separate” as the ads say, made her breasts seemed poised to spill out onto the table as she took her seat in the restaurant.

Following behind her and Jennifer as we entered the restaurant, I had two revelations almost at the same time. One, Ellen’s ass was moved so sexily beneath her dress, and second, every man and half the women in the room were watching her and Jennifer as we made our way to our table.

Jennifer was also nothing less than amazing, too. How a 14 year old girl can be transformed into a stunningly lovely and vibrantly sexy young woman of indeterminate age took and still takes my breath away. First there was the dress. Multicolored silk that also clung to her body like a second skin…her nipples pressed against the material making it obvious that one, she was not wearing a bra, and two, and she was excited about something. She was so innocently sexy I was having a hell of a time not staring at her body and openly drooling.

When we were finally seated I thanked god for the table so the tent in my pants would not be quite so obvious, although I’m pretty sure Ellen noticed as she gave me a very amused and sexy smile as I slid into the chair next to her.

“Everything okay” she asked as she reached under the table and patted my thigh, well above my knee.

be better just flattered that you two would be seen with an old geezer like me.”

not old!” Jennifer said, “But even if you were, mom and I like older men.” we mom?”

“Shhhsshhh Jenn!” not supposed to tell all our />
Another squeeze of my thigh by Ellen. I swallowed hard and tried to think of something smart to say.

No luck.

I was brain fucked. Totally.

Thankfully the waiter while slyly looking at Ellen’s display of tit to suggest that we order. Boy was I glad to see that guy.

We ordered and I added a nice bottle of Chardonnay to the meal and we relaxed and talked and even flirted a my hand would up on Ellen’s thigh and when a lightly rubbed a few times….she smiled and put her hand on mine and resumed our conversation as if everything we perfect in her world. That was the moment that I knew…that before the night was over, I was going to enjoy embarking on a very special relationship with my new tenant.

I wondered also just how hard my cock could get before it explodes?

The food arrived and we had a lovely time enjoying a truly delicious and well deserved meal…Ellen and I drained the wine bottle and I ordered I even allowed Jennifer to sneak a sip out of my glass. She was thrilled. Later on I managed to splash about half a glass into her empty water glass. Ellen didn’t object but did tell Jennifer to sip…not gulp.

We finished our meal…and when my cock finally stopped making a tent in my pants, we left the restaurant and headed back to their house. We were all tired and sleepy so as soon as we got announced she was going to bed…threw her arms around me and kissed me full on the lips.

I restrained myself and did not jam my tongue down her boy….did I ever want to. Maybe it was the wine. I confess to patting, okay lightly rubbing her cute little butt as we hugged, but that was it.

As soon as she was in her and I moved to the living room and took a seat on the couch. In less time than it takes to say “I want you” we were in each other’s arms and our mouths were fused in a searing, tongue lashing, primal, rock my world kiss. We came up for air and eyes never leaving each other we said not a word…just stared hungrily and then we attacked each other furiously. Our mouths devoured each other as my hand found her breasts and began kneading them as her hand lowered my zipper and quickly freed my rigid cock form my pants. No sooner than she had extracted me from my pants she broke our kiss and immediately lowered her lips to my the slippery head and moaning at the salty taste. She looked up at me and said “I’ve wanted to suck your cock all evening” and back to sucking and licking she went.

Meanwhile I had unzipped her dress and lowered it to her her wispy lace bra and freed her breast from their hands were full with two very firm I continued to squeeze, caress, and finding her turgid nipples, began urgently pulling and pinching both of them as Ellen drove me wild with her mouth.

so close to cumming…I can’t hold back much longer”

hold back…I want to taste you….then suck you hard again so I can fuck this beautiful cock.”

At that point, I just gave in and let it happen…I allowed myself to enjoy Ellen’s tongue rolling under and around my hands gently squeezing my balls….the feeling of her shoving my cock all the way to the very back of her throat…and then resuming sucking and massaging me with her tongue.

It seemed almost magical as I clearly I felt my hot thick jizzum rushing down my swollen shaft and erupting into Ellen’s eager mouth! She squealed around my cock and began to eagerly swallow blast after blast of my cum….never spilling a drop.

I lay back savoring the feeling as she continued suck the cum out of me… I was floating on a cloud of pure release… when from the corner of my eye… I saw her.

Jennifer.

Standing at the doorway of the living room…hand down her shorty pajama is rubbing her pussy as she watched her mom suck my cock. Our eyes met…and I flushed red…..but then returned my smile and brazenly pursed her lips and blew me a kiss. My cock jerked and Ellen rose up…asking “did I hurt you baby? I’m sorry if I did I sometimes get carried away.’

I leaned down and took her head in my her hungrily… pleased with the taste of my cum on her lips and eager to taste her, as Jennifer slowly slipped out of the doorway and into the hall. “No baby, that was an incredible blow job and I loved every second of it!” “Now, let me return the get that dress too lovely to ruin.”

Ellen sat up and together we got her dress and her thong off and tossed aside. I pushed her onto her back with her head resting against the arm of the couch and slid between her silken face first into the sweetest tasting pussy I had ever eaten at that point. Ellen had left a small “landing strip” of fine blond hair (another question answered) just above her mound. The rest was shaven silky smooth and was shiny with her nectar which was oozing from between her swollen and slightly parted vulva.

I inhaled her scent and then plunged into her the delicate slightly salty tasting folds at probing with my slipping a very wet finger out of her vagina siding it down to tease her anus. I was sucking and chewing softly on her labia…and then her rigid rubbery clit…her breath was coming in loud gasps….but when my finger hit her puckered back entrance she moaned from deep in her chest. My heart pounded….I thought “dear god let it be true…tell me she likes it in that beautiful ass.”

I couldn’t resist…I pushed against her anal opening and moaned as the tip of my finger slipped into her asshole. Ellen, to my delight, began shaking like she was being electrocuted. I pulled back a bit and she quickly pushed her ass hard against my finger…so I pressed deeper as she grabbed my head and literally shoved my face into her now dripping cunt. I had my finger into her ass to the second knuckle of my middle finger and Ellen was steadily moaning and muttering over and over.

I looked up at her…her head thrashing back and forth and I asked “you like that baby?”

“Oh god yes” was the reply.

“You want my cock now baby?”

“Oh god yes….but not back there….not not ready for you in my ass.” “Not tonight.” “But me that cock…fuck my pussy ‘til I scream…I am sooo horny and I need for you to make me cum…and I need />
Moving quickly I lifted Ellen’s legs upward as she folded her knees and spread her tanned thighs…The contrast of her tan and the pink of her inner labia was breathtaking! I slipped a pillow under her ass and moving between her looked up at me as I stood on my knees stroking my cock slowly enjoying the beauty of this luscious woman spread eagled before me. Ellen stared at my cock and she wasn’t the only one that was I lowed myself onto Ellen I looked up to see without her pajama finger rubbing her golden haired mound furiously as she watched me sink my thick cock into her mother’s pussy.

Ellen moaned as I entered her at least half of my thick 7” cock on the first thrust….I moaned and looking up at and thrust hard into Ellen’s cunt, groaning loudly as I did so.

it baby….fuck my pussy….be rough…fuck me hard Doug….hard deep and fast!” I kissed Ellen with savage began pounding my cock into her willing love tunnel…the sound of our squishing slapping filled the room….and then I looked up into the glazed eyes of a horny young girl that was cumming all by herself, her fingers deep in her sweet little pussy..her slender hips jerking as she began to spasm internally.

I returned my attention fully back to Ellen and fucked her hard as she dug her nails into my back…and then bit me on the neck as I ravaged her pussy. The feel of her velvety pussy squeezing my throbbing cock as I fucked her with a steadily quickening pace was making my balls ache. I knew I was close…. and gasped that I was about to cum…..and asked if she want it inside her or outside.

Ellen quickly wrapped her legs tightly around my waist sinking my cock even deeper into her quivering cunt, and fairly growled as she said you dare pull out you bastard, I want to feel your cum in my pussy all night long.”

With that I slammed my cock in Ellen to the hilt….I felt it bump against her uterus and she yipped…but at that point…I couldn’t stop fucking her like an animal as I spewed thick ropes of seed into this beautiful young woman beneath me.

As I just went as raking me with her it stud… fuck that pussy give me that cum….make me your little fuck toy…fill my slut cunt….I need it soooo much.”

Fuck me! I was one happy man…..and then I remembered Jennifer…I looked up just in time to see her licking her cum from her fingers then silently slipping out of the doorway…at last…on her way back to her bed…with visions my hard cock dancing in her head…I hoped.

Ellen and I lingered for another half hour kissing and the afterglow of a very intense fuck. Before I left she insisted on cleaning my cock….and boy…did she do a good job. At 56 I can cum once and maybe twice in an evening. Three times….no way. I do believe I had given Ellen a little more time….

story by: TallStranger

Tags: fiction male/teen female masturbation young anal oral sex older male / female sex story

Author: TallStranger

Related sex stories: