Tutoring Tess

Neighbor's daughter seeks out widower next door, to help her with human sexuality lessons.

By SilverFoxMullet - Listen to the ► Podcast at Steamy Stories.

I was folding the last of my laundry, there wasn't much with just myself left in the house. My son had got married and moved to British Columbia. My wife passed on 2 years ago. Just me now, enjoying a much-too-quiet life.

Then the doorbell rang. I went to the door and opened it, only to find my neighbour's daughter Tess standing on his front porch. I'd watched her grow up next door.

 When my son had moved out ten years ago, my wife and I had occasionally babysat little Tess. It had been nice having kids around the house again. She'd grown up into an intelligent, pretty young girl. She'd also been devastated why Marie had died.

"Oh, Hi, Tess. What can i do for you?"

"Hi Mr Brock. I um, I need some help with some, uh, homework. I was hoping you'd be able to help me?"

"OK, I don't know how much help I can really be, but I can try. High school was an awful long time ago for me! Come on in."

Tess followed me into the living room and I asked her "Do you want a drink, I've got water, pop, juice, or milk."

"Water's fine" she said.

I poured two glasses and came back, handing her one as she sat there on my sofa. "So, how can I help? My knowledge of high school math is really out of date you know."

She was fidgeting and blushing, as she sat there clutching her drink and a textbook. Finally she exhaled and said "Human sexuality" as she held up the book.

I blinked at her, nonplussed. What are they teaching kids these days? The only response I could muster was "Um, what?"

She set down her book, took a drink, then set her glass on the coffee table. "Mr. Brock…"

"Call me Kenneth, please."

"Kenneth. I, I want to learn about um, you know, sex. I, my friends, they're all starting to do stuff, to fool around, and I um, I want to learn too but I'm afraid."

I sat there looking at her, unable to process what she was saying. She grew more agitated, and blushed even more. Tears welled up and slipped down her cheeks. If I have one weakness, it's a crying woman. I got up and moved to sit beside her and wrapped my arms around her.

Tess sobbed and clutched at me, crying into my shoulder. After a few minutes she pulled back, and I let her go. "Will to teach me?" she asked. Oh fuck no, I thought.

"That depends on what you want to learn."

"I want to learn about sex. I want to learn everything, I want you to teach me."

"Oh. How old are you now, Tess?"

"I'm sixteen. I'm old enough to learn about this."

Oh crap. This is bad. Really, really bad. "You may think you're old enough, but not for me, that's for sure. You're not even an adult in the eyes of the law. I'm sorry Tess, I can't help you with this."

Tears started dripping again as she spoke. "I'm sorry, I shouldn't have bothered you with this. It's just, like, all my friends, they're doing stuff, and I feel left out, I want to, but I'm scared. They all say sex is painful, or uncomfortable, or just, not great. Stuff I've read, and stuff I've watched on the internet, makes it sound like sex should be really good, really fun, but my friends say it's not. I want to learn the right way, so it's good for me."

Wow. What the hell are her friends doing? Ah, right, teenage boys. Worse than useless. Maybe I can't do anything with her, but I can help.

"Ok, I am not going to teach you, at least not any hands-on lessons, but I will offer you some advice."

She straightened up a bit, and wiped her eyes. God she was so beautiful. Very girl-next-door wholesome. The last thing she deserved was some idiot teenage boy humping at her for 30 seconds and then running off to brag about his prowess to his idiot friends.

"My first piece of advice is to masturbate."

She looked confused now. "You want me to what?"

"Masturbate, play with yourself. Look, how will you ever be able to tell your lover what you want and how you want it unless you know yourself? Get comfortable with yourself, learn how to please yourself, learn what makes your orgasms great."

She was staring wide eyed at me now, as my words started to sink in. "How do I do that?" she asked.

"Look up female masturbation videos. Watch and learn, and practice."

"Okay" she said, "What else?"

"Buy a toy. Get a marital aid, a dildo, so you can practice feeling what intercourse is like. You can use other things, but it's better and safer to use the right tools for the job. Look up a sex shop or stag shop. I'll even go shopping for you if you want."

"Oh, yes, would you, please?"

"Certainly. Now, once you are comfortable with your own sexuality, and you find someone you want to be with, make sure you tell them what you like. Don't be afraid to be demanding about what they're doing. They either do it right or you kick them out of bed."

She giggled at this, which I thought was incredibly cute. "Don't discount female lovers either. They like sex exactly the way you do. Once you get good at masturbation you'll be able to please another girl quite well."

"I don't think I want to do that, I like boys." she said.

"You mean 'men' not 'boys'. That's exactly why your friends are having lousy sex. They're playing with boys."

She nodded, so I continued. "Guys like oral sex too. In fact, if you're good at blowjobs you won't have to put up with their inept antics in bed. That's another use for the dildo, to practice oral sex. And if a guy starts to hump your face, if he starts grabbing you and pushing, bite him. You don't have to take that if you don't want it. If it's something you enjoy, then let him play, but otherwise he is there to please you, not the other way around."

Tess was smiling now, tears all but forgotten. She hugged me, and said "Thank you. I will follow your advice Mr, uh, Kenneth."

I picked up her book, flipped through it quickly, and found the section on female anatomy. I showed her the diagram and said "Learn what all your parts are, what they're for, and how they work. This is a good place to start. I'll find you a toy tomorrow and you can stop by to pick it up on Tuesday, OK?"

She nodded, saying "Thank you", and repeated herself after hugging me again.

Once she'd left I locked the door and went upstairs with laundry basket. I dropped the basket on the bed and went into my bathroom. I had such a wicked hard-on, I just had to get some relief. The very idea that the literal girl next door wanted me to teach her about sex had me hard as steel.

She might be jailbait but I could still follow my own advice, and masturbate. Of course I didn't last long at all, but I wasn't trying to last.

I went shopping for Tess on Monday, picking out a nice realistic looking dildo and a bottle of personal lubricant. Maybe it was wishful thinking, but I chose one that was almost exactly my size. The girl at the cash looked kind of funny at me, so I smiled and said "Gift for a friend

Tess knocked on my door the next afternoon when she got home from school. We exchanged greetings and I handed her the plain brown paper bag. She wanted to pay me for it but I told her it was a gift. l got a hug in return and she practically scampered next door. I silently wished her luck. ." It's great to see Tess feeling more confident about her sexuality. I'm still amazed that I'm the one she turned to for help.

The thought of this girl using her new toy to explore herself gave me fodder for my own playtime for the next week. She may only be sixteen, but she's unbelievably sexy.

Afterwards I only saw her in passing, as usual, and we'd wave and say 'Hi'. She looked happy and cheerful, and I assumed her self-directed lessons were going well, as she hadn't returned for any more advice. Part of me assumed she'd developed a romantic relationship and was handling things just fine.

Life went on, I kept busy at work, and did yard maintenance, laundry, and all the usual stuff around the house. I wasn't into playing sports, so I went to the gym a few days a week to keep in shape. My woodworking hobby morphed from a strictly power tool shop to using a lot more hand tools. It was slower paced but I found it a lot more rewarding. Thoughts of Tess faded away. I had my 'internet videos & pics' to keep me occupied when I needed it. I had no interest in pursuing a new love this late in life, so i wasn't dating or putting myself out there.

That was two years ago. Today I was in the basement shop, planing a cherry table top. It was good physical labour, and I was sweating a bit as I worked. I heard the doorbell, so I set the plane aside and brushed the shavings off my pants.

The bell rang again as I hurried up the stairs, yelling "Coming!" I pulled the door open to find Tess standing there smiling at me. "Oh, Hi there, Tess. I haven't seen you around for a while. How've you been?"

"Hi Kenneth! I just wanted to stop by for a visit, if that's OK?"

"Uh, sure, come on in, can I get you a drink or something?"

"Water would be fine, thanks."

I poured two glasses and brought them to the living room. We sipped and she set her glass down.

"So what brings you by today?" I asked.

"Same as last time." she said with a demure smile.

Last time? Shit, last time she wanted me to 'teach' her about sex. I choked on my drink.

"Uh, Last time?" I said faintly.

"I'm here for my next lesson. I turned 18 a month ago," She beamed. "And now I want you to finish teaching me about sex."

Holy fucking mother of god. She was back, and she was more beautiful than ever. She'd matured more since she was 16, with such a pretty face and solid, slim figure. I could see how nice that figure was, because she wasn't hiding it. The bright yellow halter style dress she was wearing had a deep vee displaying her lovely cleavage, no back, and came to mid-thigh on her sleek legs.

I didn't realize that I hadn't responded to her.

"Well? Will you? Please?" she asked. "I've waited two years you know. And I followed all your advice too. I'm ready for the next lesson."

"But why me, you're stunningly beautiful, you could have any guy you wanted."

"I know. And I want you." She said with resolve.

She then kicked off her sandals and stood up. Reaching behind her neck, she undid the tie holding up the top of her dress. It came undone and the dress slithered to the floor, pooling around her feet. All she had on now was a pair of lacy yellow panties

God she was perfect. Chestnut hair, falling about her shoulders. High, firm, fully tanned breasts with neat brown areolas and stiff looking nipples; her slender waist flared into nicely curved hips, which continued in a graceful curve down her thighs.

Tess stepped towards me, and held out her hand. I reached out and took it. God help me, this was so wrong, but I was literally unable to resist her. She pulled gently and I rose to my feet, stunned by her presence. A tug on my hand was all she had to provide to get me in motion, and I followed her from the living room.

She led me to the top of the stairs, hypnotizing me with the sway of her ass; then stopped and asked in a sultry voice "Which way is the bedroom?"

"This way" I said, pointing to the right. I continued to follow her, into my room, where she stopped, turned, and stood with her arm wrapped around the tall bedpost at the foot of my queen bed. "Tess…" I croaked in a strained voice.

"This is what I wanted back then, when I came to you two years ago. It's still what I want now. You said I was too young. I'm an adult now, and I want this, I want you."

"Oh god, Tess. I want to say no, I should say no, I have to say no, but I can't. You're so perfect, so beautiful, so delightful, and I can't tell you no."

She smiled, and oh man, she was so stunningly beautiful it made me weak at the knees. Like a fucking goddess. And like a goddess, no mere mortal like me could refuse her.

"Make love to me, Kenneth." She said, in a low sultry voice.

I peeled off my polo shirt and tossed it aside. The rest of my clothing quickly followed, and I stood before her as aroused as I had ever been in my life. Her smile broadened and she laughed lightly, saying "Oh you're perfect! You're just like that wonderful dildo that you gave me to practice on!"

I remembered the dildo I bought her years ago, and recalled that that was exactly what I'd picked out for her. I just smiled back at her and gave a little shrug. She laughed again and beckoned me forward. The goddess pulls the strings and the puppet moves to her will. Where did she get such sexual confidence and assertiveness?

I took her hand and walked over to the side of the bed, where I sat and guided her onto my lap, and kissed her.

She sighed into the kiss, and melted against me. Her skin was so soft, her warm, fragrant body so supple and firm at the same time. We kissed for a while, and I moved my attentions from her lips to her jawline, then to her earlobes, and finally her neck.

Tess was cooing and sighing in my arms, her firm breasts and taught nipples pressed to me. I kissed her again, harder, and brought my tongue into it. Hers came back at me to play, and we tasted each other for a while more.

When she started to writhe in a subtle manner I knew she was truly aroused, so I moved her over to lie back on the bed. Awestruck, I gazed at her, reddish brown hair fanning out on the bed, firm breasts sitting high on her chest, defying gravity and anatomy alike. I swooped down upon her breasts, stroking, kissing, licking, and fondling her magnificence.

Those coos and sighs continued, and she started adding words to her breathless sounds. "Don't touch my nipples yet" she whispered, as she directed me to the valley between her tits. I moved to the undersides of them, and thence to her areolas, as I progressed along my slow, wonderful tour.

Finally, with a moan and a push, she led me to the end of this part of our journey. Set in goose-bumped areolas, her swollen, highly sensitive nipples were my last target. I began with gentle licks, then small kisses, on one, then the other, and back. Then it was nibbles, fingers rolling them, sucking them, pressing them, and manipulating her nipples as many ways as I could. She began to writhe beneath me, her words tapering off into moans and gasps. No longer directing me, I played, I explored, I teased and tantalized her. A shudder, followed by a long sighing gasp was the signal she was done with this, and she gently pushed me away.

"Oh, Kenneth, that was wonderful! Thank you. Now lay back, I want to explore you."

I did as she bid, and Tess started touching, stroking, fondling, and kissing her way from my ears to my toes. She didn't spend too long in any one place, and she avoided my cock completely. Little questions, do I like this, or that, and little comments about what she found or liked, interspersed her explorations. She found some ticklish places, and she also found some really arousing places too. Places my wife had never found, places I never suspected I had.

By now, there was a puddle of pre-cum on my abdomen, and she shifted her position to inspect me more closely. She lifted my cock and licked the most recent droplet from it. Then she dipped her head down and lapped up that puddle. My stomach muscles flexed and clenched as she tickled me with her agile tongue. She giggled at my 'gut reaction' as she called it.

Then the most wondrous sensation hit my rigid cock. Her mouth closed over me, and that agile tongue found a new place to play. My late wife hadn't been much for blowjobs, so this was a rare treat indeed for me. Last time would have been probably 25 years ago. And it didn't stop with her tongue, amazing as it was. My shaft began to disappear into her mouth bit by bit, as she bobbed up and down ever so slowly. I stared stunned and slack-jawed in amazement as Tess worked my cock into her throat.

I kept my hands to myself, clutching the duvet, and desperately willed myself not to cum. Alas, this last was in vain, because this goddess continued to pull strings on her mortal puppet. She wanted me to cum, so cum I would, whether I wanted to or not. I groaned and muttered "I'm gonna cum" through gritted teeth. She heeded my warning by humming and pulling back until just my head was in her warm wet mouth. She redoubled her efforts with her tongue, swirling around and around my throbbing manhood. With a whimper I came, shaking and pulsing over and over into her eager mouth. She swallowed my load and kept licking and sucking until I wilted in her mouth.

"How was that?" she asked.

"Oh god, Tess, that was the best I ever had."

She giggled again. "I'm just glad you picked a toy the right size. Practice makes perfect. Although my toy doesn't cum like you do, that was a bit of a surprise. It doesn't taste bad at all, but the texture is weird."

As I listened to her words, she made me wonder, and I had to ask. "Was that your first real blowjob?"

"Uh huh. First ever. It was good?"

"Like I said, best ever. I can't believe that was your first time doing this!"

"First time for real, it was always just my toy before now."

"Wow."

"Now it's your turn to please me" she said, rolling onto her back and tugging my arm. Those strings again, pulling me wither she desired, and this time it was her most private place. I used my hands and forearms, my lips and tongue, to stroke and touch her all over. It was my turn to find her interesting places, her ticklish spots, and make her squirm in anticipation.

I touched her face and neck, kissing and stroking, and proceeded to her shoulders and arms. Another chance to play with her lovely breasts was not to be denied either, and I did indeed have her squirming now. I worked my way down her body, making sure to test every place I could for sexual suitability. She directed me to a few places that she liked, and I found some spots she didn't yet know about. She began to get more vocal, calling my name occasionally, giving hints and feedback and directions, interwoven with a progressively louder and more varied series of moans and gasps.

I stopped, and rose to preview what I was about to acquire. I softly brushed my fingers all around her panties, and her movements became more erratic, changing from a slow undulation to twitching and shuddering. Slowly, I peeled the bright yellow lace from her hips. I could scent her now, a wonderful mix of the robust and the delicate at the same time. She had a beautiful reddish-brown bush, lush and soft, that led to her sex.

I nuzzled her lovely triangle of fur, all the while drawing in her heady aroma. I discarded her panties now, and her legs fell open to my gaze. Beautiful. Exquisite, even. Her lightly furred vulva surrounded a pair of dark-edged lips, glistening with the source of that scent I was enjoying. I pushed her legs farther apart and looked up at her. She smiled back at me and said "Teach me". Fuck.

A lick, along her slit, hammered my senses of taste and smell, filling me with her. She was sour and sweet and floral and meaty, with a little saltiness from her sweat. I moaned into her as I plowed her with my tongue again, deeper, harder. More contact, more flavour, more joy! I pulled back and looked for her clit. That little peak in her folds held a secret I wanted to discover. I drove my tongue into her again and licked all the way up to try and find her clitoris. It was there, small, but firm, still buried in those folds, I could feel it. She could too, based on how she squeaked and jumped when I hit the right spot.

Her breathing was getting faster, and her thighs were flexing, so I assumed she was very close. Did I want, or even need, to tease her? I needed to know what she wanted, so I asked. "Do you want to cum now, or make it last a while?"

"In a little while, but not too long" she said as she brought her hands down to run fingers through my hair.

Perfect. I wondered if her other lovers had asked the right questions, or had she had to guide them? No matter, I have the here and now to deal with. I pulled her labia apart gently with my fingers and played my tongue over the wet pink flesh revealed within. Her hips gyrated against me, so I continued to play at this. When my nose bumped her clit, she jumped and squeaked again.

I worked a fingertip into her opening, swirling it around to maximize the stimulation, while at the same time I began to gently lick and kiss her clitoral hood. A shuddering moan indicated I was on the right track, With feather-light touches around her clit, and my finger slowly working deeper into her passage, I increased her stimulation. Those gyrations increased, and my licks to her clit became less subtle, more direct.

Tess whimpered as I rolled my finger inside her, and sought her G-spot. When she cried out suddenly, with an accompanying shudder and thrust of her hips, I knew I'd found the right spot. I attacked her clit with more gusto, lapping and flicking at her, as my finger continued it's internal foray. She came, she came with abandon. Squealing and thrashing and calling my name, she practically bounced on the bed. I had to hold her hips firmly with my arms and my free hand just to stay connected to the vital spots and continue to stimulate her.

She seemed to cum at least twice, possibly thrice, before the grip on my air went from pulling to pushing. I relented, and rose to look down at her, her face and chest flushed, sweat beading her forehead, and the most beautiful expression on her face. She looked like the goddess she was.

"Oh god Kenneth, that was the most amazing orgasm I've ever had! What have you done to me?"

I slid up to lie beside her, cuddling together while she regained her breath and her senses. "That was wonderful" I said. "I enjoyed you so much, and you seemed to enjoy it too."

"The best ever" she said, paraphrasing my earlier comment on her own oral efforts.

"Your other lovers didn't perform so well, then?"

"There are no others. just me and my toy. I've waited and practiced and dreamed of this day." Her hand slipped between us to fondle my hardness, which was back from it's slumber.

"No one? But I though you wanted to learn…"

"I wanted you. I told you so. I wanted to learn, and I wanted you to teach me. All you could give me was advice and my toy, so I made the best of what I had. Can we start our next lesson?"

"Tess? You're still a virgin? Are you sure about this?"

She laughed, saying "If you're wondering about my hymen, that toy took it the very first day I got it. I went straight home and tried it. Slowly, carefully, and immediately. And every day since, I've practiced and practiced, hoping that when I was ready, you'd accept me. That you'd teach me the rest."

"You are so beautiful, so amazing, I don't know how or why I got so lucky, but you're here. And I will not disappoint you."

I sat up next to her, and swept my gaze and my hands along her nubile young body. "Did you bring any condoms?" I asked.

"I'm on the pill, and you are my first lover, do we need one?"

"I haven't been with anyone in over 5 years, and before that I had a vasectomy. So I am clean and sterile."

"Make love to me, Kenneth."

"For your first time, I want you on top."

She laughed and we switched places on the bed. Straddling my hips, she leaned in to kiss me fervently, passionately, until we were starving for oxygen. I could feel her wet heat against my hardness, as she slowly shifted her weight on me. Finally breaking our kiss, she sat upright, raised herself aloft, and reached for me.

I felt her hand moving my cock around, as she tried to position me just so. "I never tried this way with my toy. It doesn't lend itself to this very well. I'm usually on my back or on my hands and knees." Then she pressed herself down onto me, taking it slowly, gently. She leaned forward to plant her hands on my chest. "Oh god, this is so good, sooo goooood" she groaned. Bottoming out, she sat staring at me, gently running fingers through the graying hair on my chest. "Wow. I thought when I saw you, that it would feel just like my toy. But it doesn't, not at all. This is so much better!"

With that, she started to play. She bounced up and down for a while, breasts wobbling, hair swirling, suddenly yelping and shuddering on me as she came. Collapsing on me, breathing hard for a minute or two, whilst her pussy throbbed and rippled on me.

Smiling that amazing smile of hers, she pushed herself back up, and started grinding on me in little circular motions. This apparently worked even better, as she kept it up for about 5 minutes before squealing through a couple of orgasms. Once again, she slumped down onto my chest, and I could feel her heart beating madly in hers.

When her pussy relaxed again, and she stirred, she sat up and said "That was better than anything I've ever felt. Even better than your wonderful tongue. Can we trade places now?"

"As you wish" I said.

"Oh Westley!" she replied with laugh. "Farm boy, make love to me now!" she demanded.

With a chuckle, I rolled her over and we kissed again. I reached down to guide myself into her beautiful warmth, and god she was tight. I knew I wouldn't last long like this, and I told her so. "I've already had the best time of my life, please just enjoy me, the way I enjoyed you." she said.

I kissed her again as i began to slowly push my aching cock in and out of her. We could hear the wet sloppy sounds of her pussy as I fucked her. I pushed myself up on my elbows and tucked an errant strand of hair behind her ear. Her smile was amazing, and she felt so alive beneath me! I rocked my hips as my thrusting increased in force and speed, which stimulated her clit. Her smile changed to laughter as she approached orgasm, crying out to me "Oh god yes! Yes!"

I was getting closer myself, and then she looked deep into my eyes, saying "I love you". That triggered me, and I humped madly at her, pounding myself deep into her, over and over, until I spasmed in bliss. I felt and heard her answering orgasm as we tumbled from our peaks to lay panting against each other, sharing breath, sharing heartbeats, sharing souls.

"Oh god, Tess, I love you too." This, torn from me, how and why could this be happening?

She kissed me again. "I hoped, I prayed, I wished, I waited so long for this. Thank you."

Not wanting to crush her, I lifted off her, and slowly pulled my shrinking cock from her welcoming heat. "Yipe! Hey, I thought you were fixed!" she exclaimed as my issue came pouring out of her. Too late, the duvet cover needs washing now for sure.

"A vasectomy doesn't change how much comes out, just what's in it, or not in it, so to speak. And you knew from that blowjob how much I cum."

"My toy never made this much of a mess, that's for sure." she said with a laugh.

"Let's take a shower, and then we can have something to eat, and we can talk, OK?"

She looked a trifle worried about the 'talking' part, but the shower was definitely of interest to her! We spent a long time in the hot spray, exploring, touching and teasing each other. And we did incidentally get clean. We dried each other off, and I got a spare bathrobe for her.

I made some sandwiches, and poured a couple of glasses of lemonade. We ate, and I asked her about school. She had just graduated high school with top honours, and was intending to go to Queens in Kingston, come September.

Now we has to discuss 'Us'.

"Tess, you're 18, you have your whole life ahead of you. I'm 58, due to retire in 2 years. I'm afraid that if we pursue any kind of relationship it will end badly, and most badly for you."

Once again she surprised me by simply laughing at me. "Silly man! You've probably got another good twenty years in you. Do you want to waste it mowing your lawn and doing your laundry, or do you want to live?"

I blinked at her in surprise, and she continued, "Do you think I would deny myself my true love simply because it may be cut short? Are you tied to this place? Could you follow me to Kingston?"

My mind spun, I felt totally disoriented for a moment, and I looked into those crystal grey eyes. And I was lost. Strings, pulling me out of the quiet, common existence I was in. Strings, hauling me out of a rut that I hadn't known I had fallen into. Strings, pulling on my heart, making me love again.

"Yes" I managed to choke out.

She smiled that awesome, devastating smile of hers, and said "Kenneth Brock, will you marry me?"

This had started with her tears two years ago and it was going to end with mine today.

"Yes"

By SilverFoxMullet for Literotica.

Neighbor Duties.

 Kelsie tours her new neighbor's home after he says, "Howdy." Based on a post by  RavenAngstrom  Listen to  the  ►  Podcast  a...