It was the spring of ’66 and I was halfway through my senior year of high school when it finally happened. I was neither a great student nor a great athlete. No one applying to Harvard had to worry about me taking their place in the class of 1970, and the state cross country record books were in no danger of being re-written by me. My parents tried their damnedest to bring me up responsibly, and I think they did an okay job. We lived in a quiet bedroom community on the banks of the Hudson River, and even though Pop was a fortune 500 executive and Mom was a school teacher, all of us kids were expected to work our way through high school and beyond. My particular rice bowl was lawn mowing and snow removal. I had three clients in the neighborhood in addition to our house. There were two older couples that flanked our house and a younger, childless couple that lived behind us, Mario and Toni Dellasandro. Mario was a cement contractor, who, it turns out, worked for the mob. I was totally unaware of the connection until years later; I read a newspaper article about the passing of Mario ‘Cement Shoes’ Dellasandro turning states evidence against his former employer.
His wife, Antoinette, was a stay at home trophy that Mario liked to show off. I can fully understand why! She was absolutely gorgeous! She may not have been Dolly Parton in the breast department, but what she had was very easy on the eyes, and she wasn’t particularly bashful about showing her God-given assets and I spent many a summer afternoon looking out my window at the stunning redhead next door as she sunbathed while reading a trashy romance novel.
One Saturday afternoon, I was sitting in our garage, chores done, lawns mowed, playing an old guitar I had picked up at a garage sale. I was strumming along to a Peter, Paul, & Mary record I was playing on an old console radio-phonograph. Toni, as she preferred being called, came over to pay me for mowing her grass, wearing a pair of Bermuda shorts and a tee shirt style top that showed no signs of a bra underneath.. Luckily for me, I was sitting down with my guitar in my lap, for it hid the instant and raging erection that appeared seconds after she did. Unlike all the other teenage boys of the era, I was not smitten by the sight of Annette Funicello. My fantasies were fueled by Toni Dellasandro!
“That’s very nice!” she said as she bent over and handed me two crisp, new, dollar bills in payment for my landscaping services. “How long have you been playing?”
Making sure that the guitar did not slip and show my uncontrollably lust-filled loins, I replied “A couple of years!”
“And who was that on the vocals?”
I told her. She said “I’ve never heard of them. Mario always plays Sinatra, Al Martino, Dean Martin.”
“It’s a different kind of music,” I said, “Not quite as refined. A lot of the current stuff has some social overtones, definitely not establishment stuff.”
Looking wistfully at the trees, she said, “I wish I could play like that.”
“It’s really easy.” I replied, “It just takes a little practice.”
“Would you teach me?” she said with a smile.
How could I say no? “Where are my manners?” I blurted out, standing up and offering her my seat, while praying that she didn’t notice the tent in my jeans. I handed her my guitar, moved behind her and said, “Put your fingers here, here, and here and strum with your other hand.” She did as instructed, smiled again, and looked up at me. “There you go! You’ve learned your first chord!”
She stood, trying to hand me back the guitar. “That was nice, but I have to go get the chores done. It’s Mario’s poker night, and the house needs to be spotless. Thank you for the lesson.”
Not accepting the guitar back, I said, “Keep it! I’m getting a new one, and you need something to practice with.”
“Are you sure?”
“Yeah! Go ahead!”
“Only if you come over at seven. Mario’s poker buddies will be in the basement, and you can show me more. I’ll pay you for the lessons.”
“Deal!” I said standing up and offering her my hand, totally forgetting the tent pole on my pants until it was too late.
I know she noticed! She had to! She smiled and said, “See you at seven,” and walked away, swinging that delightful ass as she sauntered home.
The rest of the day was a blur. Seven o’clock came and I rang their doorbell. Toni answered the door and ushered me into the living room. The chairs there were a little too plush to comfortably play, so I suggested using a chair from the dining room. She sat, guitar in her lap and I helped her place her hands on the fret so she could strum some chords. I seemed to work best for me if I stood behind her, which gave me a pleasant view down her blouse, as well as ease of access to her hands for placement purposes. I also hid my raging stiffy.
After about an hour, I said “You seem to be picking this up quickly,” knowing that compliments were a great motivator.
She handed me a ten dollar bill and said, “Next Saturday? Unless you have a hot date.”
“Not much chance of that!” I replied, heading home for the first of many sessions with my right hand in the privacy of my bedroom, my head filled with visions of what this gorgeous woman might look like naked.
Early spring turned to late spring which turned to early summer. The lessons progressed. She had a talent for music, and we both had fun, playing simple duets, or it would be me playing and her just listening. She seemed genuinely happy and I turned a tidy profit.
A week or so after the Fourth of July, I stopped in for our usual Saturday evening lesson, but something seemed a little off. Mario’s poker buddies were not there. Their cars were not crowded into the driveway. Mario’s Caddy wasn’t there either, but I stopped anyway. Toni came to the door wearing a short sleeve print blouse and white Capri’s and a healthy shiner. She looked as if she had been crying. “Are you okay?” I asked.
“Yeah! You should see the other guy!” she joked as she invited me in. “Just a little accident. Nothing to worry about.”
“No poker game tonight? I don’t see any cars in the drive.”
“No! Mario’s out of town” she said, adding, “On business!” with a sneer.
“We can put this off until next week if you want,” I said, feeling as if I was intruding.
“Oh no! But if you don’t mind, I’d just like to hear you play, tonight,” she said wistfully.
So we settled in the living room, her on the couch, me on a dining room chair, strumming away, trying to put together a string of upbeat songs, my way of trying to cheer her up. It was obvious right from the get go that her heart wasn’t in it, and she finally broke down and started crying. Coming from a family where the women outnumbered the men, I was especially aware of the power of hormones, so I put down my instrument, crossed the room and offered a hug. Pressing against me, she seemed to be holding on for dear life. “If you want to talk about it, I’m a good listener,” I whispered into the mass of red hair atop her head.
“I’m sorry.” She said looking up at me. “I shouldn’t burden you with my problems.”
“Go ahead. I can be discreet.”
“I……I just found out this morning that Mario is doing his secretary. He’s even taken her to Chicago ‘on business’.”
“Well, all I can say is, he’s an idiot. If I was in his shoes, I’d have to find a way to work from home.”
A slight smile came to her face. “Thank you for the compliment, even if it isn’t true.”
“Oh, but it is true. Mrs. D, you are a knockout!”
She grabbed my face with both hands and pulled me down laying a lip lock on me like I’d never had before. It all happened so quickly that I responded almost automatically, my tongue searching deep in her mouth as soon as her tongue vacated mine. I was very much caught up in the moment, pulling her tight to me, pressing my hard-on against her belly. My hands, holding her by the waist, slid down over her the globes of her ass, kneading the firm flesh under her shorts.
Her feet left the floor and wrapped around my waist as she broke the kiss for the briefest of moments. “Call me Toni,” was followed by, “The couch! Head for the couch!.”
I did. Laying her out on her back, her legs still locked around my waist, she pulled me down on top of her, continuing the deep kissing as she ground her hips against me. Grabbing my hands, she placed them against her breasts, moaning as my hands cupped over her bra.
This was all going way too fast for me, and I broke the kiss again. “We really shouldn’t be doing this Mrs. ..Ah, Toni.”
It was about this time that she realized that, just because I was 18 didn’t mean I was experienced. Holding my face in her hands again, she said, “It’s okay. We can go slow.” Seeing the panic in my eyes, she added, “Just how far have you gotten, you dear, sweet boy?”
“Ummmm…….second base?” I said, my hands still on her chest.
“It looks like you need some lessons. Let’s get started,” she said, unbuttoning her blouse and exposing her bra clad chest for my viewing pleasure.
Smiling back, I replied, “That, I can do!”
We resumed kissing while I fumbled with the clasp, finally feeling it give way. My left hand pressed into the warm flesh of her back and began to slide around her side and up under the padded cup of her bra. Her skin was soft, almost hot to the touch and she murmured into my mouth as my fingers danced across her nipple. Needless to say, I was as hard as a rock as her hand cupped my manhood through my pants.
She removed her blouse and bra, exposing her small but shapely freckled breasts, topped by lust swollen puffy nipples that silently screamed for attention. My eyes were riveted to them. I wanted desperately to shower them with kisses. Reading my mind, she whispered, “Go ahead! I know you want to! I want you to!”
I leaned down, my lips brushing against her right nipple. I felt the pressure of her hand on the back of my head, letting her pull me in. My mouth opened, surrounding her areola and my tongue brushed against her nipple and I began to gently suck. My hand cupped the other, gently massaging, listening to her purr.
Switching to the other breast, my free hand dropped to her lap. Her legs opened and I began to massage the crotch of her Capri’s. After a minute or so, she said, “You’ll have much better luck if you take them off.”
I blushed. “Is it that obvious?”
She smiled, answering, “I think its sweet….. and a little hot, too” She raised her hips off the couch to give me better access to her zipper.
Shucking her pants she sat there in only her white, cotton panties. She looked so fucking hot! I didn’t know what to do next! Sensing my indecision, she put her hand on my head, pulling me into her cleavage. I breathed in the sweet, sexiness of her perfume. “Chanel No.5. You like?” As if she couldn’t tell! I nuzzled between the fleshy orbs, kissing the soft mounds, alternating sides, working my way uphill to her nipples, which I couldn’t get enough of. Sure, in my limited experience, I’d felt tits before, but never progressed to the kissing and sucking parts. This was new territory for me and I was determined to make the most of it.
Toni was as determined to make the most of me as well, grabbing my hand and cupping it over her panty clad pussy. I’d read enough smut to know what to do, so I gently rubbed, feeling her swollen mons through the flimsy fabric. I could feel the panties dampen and hear Toni cooing. I had to be doing something right! I slid my hand inside the waistband of her undergarment, combing my fingers through her bush. “Oh, yes…don’t stop!” she sighed. My middle finger reached her slit. She was slick with her own juices and my finger curled inside “Finger me ‘til I beg!” she added, tightening her grip on my head.
I had never felt anything so incredibly good. The heat and humidity of her pussy; the moans from her throat; the stiffened nipple responding to the touch of my tongue was making me painfully hard. I wanted this woman and, as far as I could tell, she wanted me.
My finger plunged easily in and out of her wetness. “Rub your thumb on my clit!” she whispered, “Yes right there! That’s it!” Her moans got a little longer and a little louder as I worked to get her higher. “Oh fuck!… Oh yes!….Don’t stop!……Ahhhhhhh!”
Her wetness exploded onto my hand and dripped through my fingers to the couch below. She pulled my hand from her panties and licked one of my cum-soaked fingers “Mmmmmm! Wanna taste?”
Unlatching from her breast, I allowed her to feed my middle finger into my mouth. The scent of her; the taste of her were magical. Like nothing I’d ever smelled or tasted before. The muskiness was intoxicating.
“You want more?” she asked with a triumphant smile, “You’re gonna have to wait. I get to taste something first.” I knew what she wanted me to do and I eagerly accepted, apologizing in advance for my lack of experience. “That’s okay!” she said, “I’ll give you guidance if it’s necessary. But, I think you’ll do just fine on your own. In the meantime, just sit back and relax. You’re gonna enjoy this.” She unfastened my jeans, unzipped the fly and let my swollen manhood spring forth, fully tenting my boxers. “This looks yummy!” she said as she grasped the base of the shaft and stroked upward. I saw the droplet of clear liquid ooze from the slit in my crown and saw the gleeful look on her face as her tongue snaked out and swiped it away. “Mmmmm!” she said just before pressing her pursed lips to the head and sucking it into her mouth.
I thought I had died and gone to heaven! The woman of my dreams was sucking my cock. My very first blow job and Toni Dellasandro was on the receiving end! It seemed like she had hardly started and I felt that familiar rumbling in my gut. That feeling that screams ‘I’m gonna cum’ just before you do. I grunted as my cock twitched and spat long strings of sticky white cum into Toni’s eager mouth.
Totally embarrassed by my performance, or lack of it, I mumbled an apology, to which she replied, “It’s okay! That just means you’ll last longer next time,” adding, “Damn! That was delicious!”
Pulling my pants and boxers all the way off was her way of letting me know that it was my turn to please her.
She slipped her dampened panties off and laid them on the arm of the couch, opened her legs, and invited me in. I knelt in front of her, taking a moment to take in the sight of her pussy – the thick, wiry, orange-red hair, trimmed a bit around the legs pointing to her lust swollen clit and fat pussy lips, still shiny with her juices. “Taste me!” she said.
I crawled between her outspread thighs, kissing each as I got closer. Her scent filled my nostrils, making me painfully hard. I tentatively swiped my tongue along her slit, tasting her again. “Tongue fuck me!” she whispered. I pushed my tongue deeper into the crevasse of her sex, gathering more of her musky, sweet flavor. “That’s it! Eat me! Make me cum with your tongue!”
With her hand on my head to guide me and, all too willing to oblige, I stabbed and then dragged the tip of my tongue the length of her, ending with her clit. “Flick it! Flick it with your tongue!” she pleaded. Closing her thighs against my ears and raising her hips, she moaned. “Your tongue feels so good on my cunt! Don’t stop!”
The rolling of her hips smeared her essence from my nose to my chin and I drank what I could as I continued to lick and suck on her womanhood. Her moans and mumbling spurred me on as I surrounded her clit with my lips and feathered it with my tongue. “Oh God, yes! Just like that! Oh fuck! Finger me! Finger me ‘til I cum!”
I slid my finger in as I continued to suck her clit, my nose tickled by her hair. Warm and tight, I withdrew and plunged making her squeal with delight. Her hands combed through my hair, holding my face tight to the soft flesh of her leaking pussy. I short order, she came again, my finger feeling the muscles of her cunt squeeze, fresh honey poured from her and covered my face. Pulling me up by my hair, she kissed me passionately, our tongues slithering in and out of each other’s mouths. Still panting from her orgasm, she said, “We need to go to the bedroom! I need you to fuck me! Now!” she pleaded.
We got off the couch and practically ran to the bedroom. Splaying herself across the duvet, a ‘come hither’ look in her eye, she whispered, “I want you inside me!”
I crawled up between her thighs, gently kissed her clit, ran my nose through her bush, breathing in the heady scent of her musk, kissed her belly button, continued up her slim, prone body, sucked each nipple into my mouth for a moment, and kissed her throat.
My cock nestled between her cunt lips. She raised her hips slightly and I slid inside easily. My breath caught in my throat as my cock felt her cunt for the very first time. My lips caressed her ear and hers nibbled mine. Throatily, she said, “Fuck me! And don’t stop until you cum!”
My hips rose and fell as my cock plunged deep into the moist heat of her clutching cunt. Our bodies slapped together as she moaned, meeting my thrusts with her hips. My hands were all over her breasts, both of us panting from the exertion.
She was right. I did last longer the second time. Building up slowly, my orgasm came, urged on by the contractions of her cunt on my cock, tipping me over the edge. I grunted like an animal as my seed spurted in long ropes, deep inside her. I tried to dismount, but she enfolded me in her arms and we cuddled for several minutes. ”I’d forgotten how good a cock feels!” she sighed, letting me roll off, snuggling up beside her, my fingers playing with her nipples.
“I had no idea how good a….a…”
“Cunt feels?” she added. Seeing my embarrassment, she said, “It’s okay! I like the word, as long as it’s not used as an insult. I hate it when Mario calls me a stupid cunt.”
“Well, I don’t think you’re stupid, and as for your…cunt… I think it’s kind of pretty, and very tasty.”
“And you, sir, have a very talented cock, and it’s pretty tasty too.”
She tried, to no avail, to get me re-animated. I think she wanted more, but I was just too empty. She turned to me and asked, “Another lesson next Saturday?”
Smiling, I replied, “Guitar? Or did you have something else in mind?”
We parted, both looking forward to our next meeting, but it never happened. The following Saturday, I showed up but found no one home, just a package with a note. “These are for you to remember me by. It’s probably better for both of us if we don’t meet again. Thank you for a most wonderful night. I will NEVER forget it!”
The package contained the panties that I had slipped off her. I knew I would have to hide them well. My mother would never have understood!
My reverie was interrupted by the doorbell. I answered it, opening the door to a fifty something redhead who looked remarkably like her sister, only with greying red hair. “Hi!” she said, “My name is Dierdre Dellasandro. I understand that you knew my mother.”
