Note: As per my other stories, the character names are all changed on the off-chance that there is someone who recognizes any of the deions of living arrangements or furniture. If this is the first story of mine that you are reading, I have two prior stories, and this is third story of my teenage sexual encounters. While the other two stories are not necessary to read, there are a couple allusions to the other stories in this one. Once again, while the verbal interaction may not be accurate, the physical interaction is.
When I was about 13, a family friend needed to move out of her apartment. She shared a place with her younger sister, and her sister had recently become engaged. Rather than having to pay for a 2-bedroom herself, Joan offered her younger sister the apartment and needed a temporary place to live. What was supposed to be a month visit, maybe two at the most, turned into a stay between three and four years in length. Not being able to afford an apartment, except in some of the less-desirable places to live in Toronto, my parents insisted that she continue to live with us until she found something suitable. Eventually, she was just like another part of the family, and it wasn’t such a bad deal for my parents; Joan offered to help out around the house in many ways. When she first moved in, my parents had just entered their fifties, and following my father’s financial success, they were very interested in doing a lot more travelling. Joan helped out by looking after me and my older brother, and checked in on my sister who had recently entered her first year of university.
Joan was not a striking beauty by any stretch of the imagination. She had very fair, shoulder-length blonde hair that she typically kept in a tight pony tail. She was probably a good forty or fifty pounds over what most people would consider ‘comfortable’. For a woman standing at 5’7”, she was bordering on obese, but kept an active lifestyle to the point that she wore the weight well. She was chunky, but not in a completely repulsive way. The only real problem I had with her appearance was her nose. She had two grey-blue eyes, but you could barely notice them with her rather large nose protruding from her face. Despite what I saw as her only real physical flaw, I often found myself masturbating to fantasies of Joan. Our relationship was somewhat bizarre in that she fell somewhere between an older sister or cousin, and a mother figure. She helped raise me through some of the more challenging years of a young adult’s life: puberty.
Joan was a very nice lady. She was always concerned for my well-being, and wanted to make sure that I had space when she was in charge. She didn’t hover if I had friends over, and she generally was ok with my friends and I drinking and smoking as we got older. When my parents would go out of town on one of their suddenly frequent vacation to Europe or the Caribbean, Joan was there at my beck and call, despite working a fulltime job herself. She would get up earlier to drive us to school, she would make dinner, and she would basically have very minimal social life while my parents were out of town. The woman had gone from dating occasionally to being a sweatpants and laundry-day shirt kind of lady on a daily basis.
As the years went by, Joan was very helpful in shaping the man I was to become. She was open and honest about things that I was just never comfortable talking about with my family. I was very clueless of any sexual effect it may have had on her, but she was very understanding when I came to her to talk about sex and relationships. As I said before, she was kind of somewhere between a much older sister and a mother. Joan wouldn’t hesitate to get into the details of sex, and even told me how to properly eat a girl out. She had appeared overjoyed when I told her of some of my first sexual experiences with Emily, my first real girlfriend, and her eyes always seemed to light up whenever I’d come into her room before she went to bed, so we could chat about anything and everything.
The summer after I finished tenth grade, I had absolutely nothing to do. I was never a camp kid even though I was in Beavers, Cubs, and Boy Scouts from the age of five. My father wanted me to work at his offices during the summer, but I managed to get out of that situation by explaining that it was my last real summer as a ‘child’. I assured him that I would work for him the following two summers before I went off to university myself (I was very fortunate to not have to keep a part-time job while I was in high school, due to my father’s success).
In the last year, I had turned from a moderately flabby, but not overweight, individual into a bit of a jock. I spent more time in the gym than I did doing homework or studying, and I was very proud of the body I had shaped – it had helped me get my first girlfriend, and I had had sex with six different girls since my personal transformation had occurred. The only shitty thing about my summer starting was that I was no longer getting it on the regular from Mrs. Curtis. This meant that I would be wholly relying on parties and maybe getting a new steady girlfriend to have any amount of sex.
By late June, I had been out of school for about two weeks, and Joan had noticed a definite shift in my mood. I hadn’t fucked for a week, which was pretty on the low side considering I had been having sex at least three times a week for the last six or so months. She was acting cheery around me, and was taking a lot more liberties with our time spent together. She had begun putting her hand on my leg, and wearing skimpy noodle-strap tank-tops that barely held her in rather large breasts.
One evening in early July, I was sitting in the kitchen eating dinner. I had no plans because it was a weeknight and half of my friends were either at camp or on vacation. Since no one was home, I had been walking around the house with no shirt or boxers on – just sweatpants. As I was eating, Joan came home and made her way into the kitchen to say hello. Before she even got within five feet of me, I was incredibly aware of how plastered she was. She was slurring her speech a little, walking very carefully, and most of all, she reeked. She smelled like she had smoked a few packs of cigarettes and then had a dip in a bath full of booze.
“How was your day,” I asked Joan, trying to be polite. I was a little concerned because I’d only ever seen her this drunk once before, and she wasn’t living with us at the time.
“It was exquisite,” she managed to mumble.
“How did you get home?” I hoped she hadn’t driven.
“Got a cab. That chicken smells awesome. I had salad for lunch. Can I have some?” She was muttering non sequiturs, and had already started picking pieces of chicken and feta cheese out of the salad I had prepared before I could respond.
I got up and quickly went across the kitchen to grab her a glass of water. She was going to be pretty hung over in the morning unless she downed a few litres before she passed out.
Returning to the tables, I started pressing for information that I knew I already had the answer to. “Any hot guys at the bar?”
“Of course there’s hot guys at the bar. That’s why we go after work.”
Smiling slightly, I got her another glass of water. Judging by the amount of time Joan spent at our place on weekends, I wouldn’t be at all surprised if my two sexless weeks were peanuts compared to her current dry streak.
“You should go home with one of them sometime. You deserve some fun too, you know. Jake (my brother) is moving out in a couple months for school, and I’m old enough to look after myself.”
“I need them to want to go home with me too, sweety.” She had struck out with whatever guy she’d been hitting on at the bar.
I knew that this situation was likely headed towards what I call ‘blubbery drunk’, when someone is just so incoherent that they start crying a little. The next thing you know, they’re bawling and sobbing uncontrollably, and you can’t understand a single word they’re saying. Refilling Joan’s glass a third time, I set the glass down on the table in front of her chair and gave her a big hug around her neck from behind.
“You’re probably too good for any of those fucking idiots anyway,” I reassured her. I could feel her body fighting off some trembling as she tried to maintain some decent level of drunken composure.
“I’d kill to have a hard cock in me tonight.”
I was floored. Obviously most people like sex, that’s no secret. But my parents and their friends had never really been ones to openly discuss their sex lives. Yes, my father made innuendos, but they never outright discussed any aspect of fornication with each other or in their pasts. I wasn’t really sure how to handle the situation, so I sat down beside Joan and offered her another hug from the front.
As we embraced, I could feel her loosen up a bit. She was definitely calming down, and her body was relaxing a bit.
“I’m sorry,” she whispered to me, briefly catching my eye before looking down at my crotch.
I hadn’t even noticed her hand until that moment, as it was quickly climbing up my leg. I wasn’t aware that how I was sitting was pushing my cock against my sweatpants and giving her an outline of my still flaccid member. I was maybe a tiny bit aroused before hand, so my cock had a tiny bit of life, but nothing that would have drawn any attention.
As I stood up to try to back from her, Joan’s hand darted forward and hooked into the front of my sweat pants. Rising, my pants dropped and my limp cock was suddenly inches from her face. Grabbing Joan’s hands before anything happened, I drew my hips back, trying to remove myself from this situation before it got worse. How embarrassed would she be if she touched me while she was absolutely hammered?
Before I could flee the room, Joan had pushed me back. With the back of my legs resting against a chair already, I fell into the seat and wasn’t quick enough to move before she was on me again, with the determination and unwillingness to quit that comes with being incredibly drunk. My pants had fallen around my ankles, so she reached out and grabbed my flopping penis well I tried to pry her grip open. Looking me in the eye for only a moment, her head suddenly bobbed down to meet its prey. As my cock entered her warm mouth, my resistance quickly lessened, and my hand that was on her head had gone from trying to pull her away to trying to force her into a rhythmic assault.
My cock was rapidly getting harder, and soon my full eight and a half inches was getting wet with her spit. I pushed back gently on her to allow myself to stand up. Grabbing her ponytail in my right hand, I held my cock straight with the left, lining up her throat for what was about to come. I was willing to allow myself to become lost in ecstasy in a moment.
Out of nowhere, I hear keys in the front door. My parents have arrived home from their dinner date and have brought their friends back here for coffee. Scrambling to shove my rock hard dick back into my pants was a challenge, especially with Joan not sensing the reason for my urgent movements. As my parents turned into the kitchen, they were greeted with me sitting opposite Joan, looking like we were just chatting. Had they come into the kitchen before passing into the living room, they would have noticed that Joan’s leg was stretched under the table, continuing to trace my cock through my pants.
“How was work, dad?” I asked as he came in to the kitchen to get the coffee started.
“Shit,” he mumbled. “Can you go put a fucking shirt on? At least until the Lee’s leave.”
“I will in a second, dad. Just gonna finish my dinner.”
As he left the room, Joan stumbled her way over to me, kissing me full on the lips. She reached down to continue to play with my cock before I swatted her hand away and told her this couldn’t happen. She pouted and was going to start crying again, so I quickly threw her over my shoulder and got her downstairs to her room. I left her fully clothed on her bed, with a couple bottles of water and a garbage can. I then went to my room to get dressed, before saying hello to the Mr. and Mrs. Lee.
An hour later, after the departure of their guests, my parents went upstairs to watch some tv before they went to bed. I knew I needed to go check on Joan. As I descended the stairs, I reasoned to myself that it wasn’t because I was horny and wanted it (did I?), but because I genuinely was worried about her. She was pretty drunk when she got home, and if she had rolled over and thrown up in her sleep, she could easily choke to death.
“Joan?” I knocked on her door, pushing it open slightly so I could listen for a response. Dead silence.
I opened the door a little more, continuing to quietly call her name. I had dimmed the lights before I left her earlier, and it was making it challenging to see – the light from outside was quickly fading, and I didn’t want to startle her or myself by turning the lights on full. Carefully feeling my way along the wall, I made my way past the small alcove-entrance to her room and rounded the corner to find her in an awkward position. Her upper body and part of her thighs were on the bed, but everything else was hanging over the edge. She had definitely been coherent enough to get up at least once in the hour since I hastily deposited her on the bed, as she had changed into her sweats and that tantalizing noodle-strap top. Lying face down on the bed, I slowly crossed the few steps to her still body before once more calling her name and gently shaking her leg.
All Joan did was emit a low moan, as though she were trying to say something. Despite her condition, she was probably still capable of carrying a conversation, though she was not making it easy.
I leaned down to get my head closer to her face.
“Joan, are you ok?” I rubbed her shoulder before trying to carefully turn her over.
As she rolled over, the mounds on her chest succumbed to gravity, pushing the sides of her top out from her body. My penis began to harden, as I remembered how good it felt to have my dick in a mouth again for the first time in a few weeks. I kneeled on the bed, straddling Joan, as I was going to try to hike her up farther onto the bed so she was at least in a comfortable position to get some good rest. As I dipped my body to gain some leverage, my hardening cock ground into her
After getting her head up onto her pillows, I made a snap decision. Standing up quickly, I threw my pants to the side, and quickly knelt down, my ass resting gently on her hips. I knew that if she woke up and didn’t remember what had happened earlier, I was in for a world of trouble to try and explain what I was about to do. Lifting her neck up, I pulled her tank top up and off her body, letting her huge globes flop back down against her. I shuffled up the bed and rested my cock between them, with the head on her lips. Grabbing the side of each beautiful mound in one hand, I started to fuck her tits, my cockhead stabbing her face with every thrust.
Despite feeling pretty good, after only a minute or two of this, I knew it was going to be uncomfortable if I continued to do so. After trying for a few moments to get her mouth opened enough to stuff part of my cock in, I resigned myself to jerking off a big load, spraying her tits and mouth equally with my salty sperm. Reaching back, I cupped her pussy through her sweat pants before squeezing the last remaining drops of my juice out onto her lips.
One of the most erotic experiences of my young sexual life, and the other person hadn’t even been awake to experience it. I immediately began to sense the repercussions of Joan waking up with dried semen all over her naked breasts and face. Jumping off the bed, I got a washcloth from her bathroom and cleaned her up, before sliding her tank top back on. The last thing I did was leave a note telling her that we definitely needed to talk about what had happened, and we could talk the next night after she got home from work, and before she went to bed. I ended by telling her I hope she felt better, and that I had tried to force feed her gallons of water, leaving out the other thing I had tried to shove in her mouth.
The next couple weeks went by, and Joan had been avoiding me as best she could. She would come home having already eaten, or with takeout, and go right into the basement without more than a quick hello to my parents, completely ignoring me. I felt slightly dejected, and was pretty sad that I’d screwed up my awesome relationship with a very nice person. Just after my mother’s birthday in mid-July, my brother announced that he needed to go visit the school he had chosen to go to in Boston to finalize some things, register, and make sure that everything was going to go smoothly with his freshman year of university. My parents quickly decided that they would go with him, and made an entire week of what should have been a one or two day visit. Opting to give him a graduation present of travel, the three of them were going to be spending five days after the college arrangements were in place to drive down to New York and visit parts of the north-eastern United States.
With my sister taking an accelerated program, she was stuck in school all summer, leaving Joan and I alone for a week. Joan must have accepted that it was useless to avoid me forever, because she finally spoke more than ‘hello’ to me for the first time in a couple weeks. My parents and brother had left Monday morning, and when Joan arrived home that evening, she walked into the kitchen to find me wearing just the sweatpants that had become my summer uniform.
“Can you go put something more appropriate on so we can talk?”
“Yeah, I’ll be back down in a minute,” I told her as I bolted up the stairs to grab a tight hoodie.
Returning to the kitchen, Joan was lost in thought dicing some vegetables for dinner and didn’t even notice me come back in.
“So we’re going to talk?” I snapped her back to reality.
“Look, sweety. I have a vague memory of doing some things that I’m very embarrassed about a few weeks ago.” She held up her hand to silence me as I was going to tell her that it was ok. “Ever since I’ve been staying with you guys, my life has become increasingly more isolated. I went from living downtown to living in the suburbs. I went from sharing a place with my sister to being a permanent houseguest. While I appreciate everything your family has done for me, it has also sped up a certain part of my life that I wasn’t really anticipating for some time.”
“What do you mean?” I was very confused with the direction this conversation was taking.
“I’ve become a spinster. I don’t go out that often, I had less dates and sex in the last three years than at any other point since I was a teenager. I wear sweats around the house, and I became comfortable. The worst part is that I’ve been wanting sex more and more being in this house, and have just been unable to get it. I’m not in shape, I’m not the prettiest woman in most conversations, and I’m getting over the hill.”
“What the fuck are you talking about?” I scolded her. “You’ve got a pretty decent body,” I reassured her. I was lying a bit, but this woman was too nice and caring to feel this way.
“You’re just being nice,” she responded gloomily. “I know what I am, and I know what you are, and what I did a few weeks ago was completely unacceptable.”
“What do you think happened?”
“Well I remember blowing you even though you didn’t want it. That’s about it.”
“Well two things,” I shot back. “First, you were drunk out of your mind, so I think I can give you a free pass on that one. Second, what sixteen-year-old doesn’t want head from a gorgeous lady?”
Joan smiled at me, beginning to blush. “Most young men are fine getting head from less-attractive women too.”
“Would you stop that? You’ve got great hair, beautiful eyes, and you’re not that out of shape. You’re pretty close to a great booty, and your tits are pretty magnificent.”
“My tits?” Joan cut me off.
I knew I’d fucked up. Scrambling to try to find a way out of the situation, I began muttering, “Uhh... yeah.. you know. That tank top.... you have nice tits.”
As Joan looked at me, searching my face for what was obviously missing from the story, I could feel my cock start to harden in my sweats.
“That night...” Joan trailed off. “Rob, what happened that night? Tell me the truth.”
I told her exactly what had happened that evening up until the point my parents got home and I had carried her down into her room.
“So nothing else happened?” She was grilling me. Somehow she knew something else had gone on that evening.
“Well, I went to check on you later, but, uhhh..... yeah..” I started to mumble again.
“Ok, I believe you,” she said, opening her arms for a hug.
Despite my throbbing cock, I stood up and hugged into her, my ass sticking out to stop her from noticing my arousal.
Suddenly, Joan grabbed my ass, grinding my hard cock into her warm crotch.
“I’m not drunk tonight, Rob,” she moaned, rubbing her body along my shaft.
“Joan, I really don’t... I don’t think we should,” I stammered.
“Your dick thinks we should,” she countered.
Her hand snaked down into my pants, closing tightly around the base of my throbbing cock. With her free hand, Joan roughly grabbed the back of my head, pulling my mouth into hers.
I hadn’t really been fighting it to this point, but I quickly spun her around, before tackling her to the ground. After some struggling, Joan ended up on her back, my shins carefully pinning her arms down as she wiggled her hips a futile attempt at freedom.
“Rob,” Joan began.
“Don’t move,” I warned her. Carefully lifting one knee at a time, I managed to shimmy my pants off, my hard shaft now visible to her sober eyes for the first time.
Replacing my knees on her arms, I grabbed her face with my right hand, my thumb pushing hard at her mouth. Despite gaining easy entrance, I continued to try to force my already enclosed thumb further.
“You haven’t fucked in a long time,” I tormented her.
“Please let me up,” she begged.
Ignoring her request, I leaned back and undid her suit pants, before shoving a hand in and cupping her pussy through her panties.
“Jesus Christ, you are fucking soaked!”
“Let me up,” she demanded once again, though definitely sounding more as though she thought she was in control of the situation.
As I slowly got off of her arms, I grabbed her hair, dragging her to her knees, and then her feet. Standing behind her, I dropped her pants to her ankles, and pulled her tightly to me. My cock was now resting between her fat ass cheeks. Holding her stomach roughly with both hands, I bent my knees slightly, allowing my hard cock to run across her panty-clad pussy. Reaching one hand up, I pulled her head backwards by her hair, biting her lip hard and eliciting a loud moan.
“You’re going to get what you want,” I told her. “But first, you’re going to give me what I want. Get downstairs and go turn on the sauna. When you’ve done that, go wait in your room.”
Squeezing her breasts through her shirt, I pushed her roughly from me. Spinning quickly to look at me, she turned and quickly went into the basement to turn the sauna on. Before she could get to her room, I silently ran down the stairs and hid in her closet. As Joan entered her room, she had already taken her jacket, shirt and bra off. Her tits sagged a little, and jiggled tremendously as she skipped towards her bed. As she bent over, I crept out of her closet.
Grabbing her from behind, I tore her panties, ripping them off her legs without allowing her to take them off. As Joan squealed in ecstasy, I pushed her face down into her pillow and climbed on top. Even though she was relatively tight from years of inactivity, she was so wet that I slid half my cock into her pussy with no trouble at all, causing her to tremble in a quick orgasm. The sound was mostly muffled by her pillow, but she was screaming like a banshee, very high-pitched and arousing.
As her brief orgasm subsided, I shoved my cock further into her pussy before pulling out and climbing up beside her.
“Suck my dick,” I barked at her.
She obediently forced my cock into her mouth, gagging at the effort.
Removing my cock from her mouth, I grabbed her once more by her ponytail, and began dragging her to her bathroom. Not allowing her to get a proper footing, she hissed as the carpet burned her knees and the tops of her feet. Pushing the door open, I pulled her up and into her shower with me. After letting the water reach a warm temperature, I pulled her wandering hands from my shaft and told her to clean my cock, my asshole, and her own body, making sure to stress that I wanted her asshole clean enough to eat out of.
As Joan quickly scrubbed our bodies with soap, I roughly grabbed her tits, squeezing them hard and pinching her nipples as I pulled them out from her body. Telling her to hurry up and finish soaping herself, I shoved three fingers into her pussy before forcing them into her mouth. Greedily licking her juices off my hand, she finished her soapy task.
Shutting the water off, I grabbed a bottle of baby-oil of her counter before grasping her once again by her pony tail. Pulling her from her bathroom, I strode with purpose from her bedroom, through the small entrance and into the hallway. My grasp in her wet hair tightened, and though it must have hurt like hell, her gaze never left my cock as it swung back and forth with each stride. Seeing that the sauna was warm enough, I got in and let go of her. As her hands tried to once more reach for my veined member, I pushed her gently away before sitting on the sauna bench and rocking back so my asshole was exposed.
“Eat my ass,” I commanded her.
Joan hesitated for a moment, a slight look of distaste spreading across her face.
“EAT MY ASS,” I screamed at her.
Quickly dropping to her carpet-burned knees, Joan’s tongue began to lick around my asshole. Reaching down, I pulled her head right into me, so that her she had an eyeful of my trimmed sack while her tongue probed my ass. I started to slowly jerk off the top of my cock, causing my balls to rub against her eyes and forehead as she continued to slurp at my hole. After a few minutes of this, I pushed her head away a foot, before lowering my cock to her mouth and pulling her back.
Gagging once more on my hard dick, Joan’s throat was closing off, trying to prevent the rough intrusion. I grabbed the back of head and pulled hard, though it was not fitting into her throat. A small puddle was forming underneath me from Joan’s mouth. Standing up, I leaned her backwards until she was on her back, her tits once again flopping into themselves. I grabbed her throat and started fucking her face, only getting four or five inches in. After allowing her to relax a little bit at this less strenuous assault on her mouth, I pushed hard, shoving my cock until my trimmed ball sack pushed over her nose. As Joan’s body began to shake and fight the renewed intrusion, I held her tightly to my groin. Pulling out to allow her to breathe, I looked with content with the spit and tears mashing together on her face.
I stood over Joan, slowly jerking my cock.
“Lube up,” I told her. She knew better than to ignore me this time – the pain would be excruciating.
After she’d applied some baby oil to her asshole, I had her kneel on floor of the sauna, pushing her ass in the air. Standing over Joan, I pushed my hard dick downward, lining it up with her fat ass. As I slowly pushed my head into her ass, Joan began to tremble a little. After a couple moments, my cock was halfway into her asshole, and she exploded for the second time, her juices cascading down her legs and onto the wooded floor. Working my cock further into her rectum, I was finally resting against her cheeks. Her ass was incredibly tight, squeezing my cock like a boa, asking it to never leave. As I slowly started to pull out and begin a light thrusting rhythm, Joan came for a third time, once again wailing like a demon possessed.
I continued to pound her asshole for about ten minutes before pulling out and telling her to suck me. Without hesitation, Joan turned around and pulled me into her mouth, jerking the base of my cock while slurping hard on my pulsing purple head. Leaning over, I pinched her nipples and roughly squeezed and slapped her tits.
“I’m gonna cum,” I moaned. “Lie down.”
As she lay on the floor, I sat right on her stomach, as she continued to jerk me off. Leaning forward on my knees, I grabbed my cock from her grasp and grabbed the back of her head, pulling her head towards me. As my cock began to twitch, I deposited load after load in her mouth and on her cheeks, chin, and forehead. After what seemed like a good twenty or thirty seconds, my orgasm ended, and I slumped a little bit.
As we exited the sauna, our sweat dripping everywhere, I pulled Joan to me and roughly pushed my tongue into her mouth.
“Go tell your boss you’re not coming in this week.”
My parents found out that Joan and I had been fucking for a number of months just before Christmas that year, and she was forced to move out almost immediately.