Alessandra

Story Info
Young man’s mature neighbour teases him and he has sex with.
11.2k words
4.7
14.9k
13
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's note: I've been experimenting with a more modern form of punctuation, documented at the University of Sussex. I hope that it doesn't impose on your enjoyment of reading this story.

Also, thank you for your comments, voting and emails. It encourages me to keep writing these stories.

######

Jay was wearing a Jesus Christ costume: with a crown-of-thorns and fake blood on his hands and feet. Most of the guests had arrived but a few were dwindling in. Such as, the neighbour from across the lane, Mrs T.

Mrs T was about the same age as Jay's parents, Gail and Ben. She was a widow living by herself in a two storey home across the very narrow lane from Jay's home.

Jay answered the door and, at first, didn't recognise Mrs T. She was dressed as a baby: wearing a cloth nappy, a short tube top that was gathered by elastic at the top but loose at the bottom, a simple bonnet and a huge pacifier pinned to her top.

"Hello Jay. I come bearing gifts. Happy birthday. Here's your present." said Mrs T, as she handed him a parcel. "And this is for me." She held up a cask of Moscato wine.

"Sorry I'm late. I forgot it was fancy dress and had to whip up this."

"Thanks Mrs T." said Jay, as he took the present. "You look fantastic."

"Do you like it?" asked Mrs T, as she rotated on the spot. "My feet are a bit sore. I walked across the lane without shoes. That bitumen is rough."

"Come in come in." said Jay. "You've outdone yourself with your costume. I love your baby look, Mrs T."

"Thanks, Jay." said Mrs T, as she entered the premises. "Ooh, this party is rocking."

The party was a success: most people, who wanted to be drunk, were drunk; some people danced to the music; many just drank and talked; some slipped outside for a smoke and returned even more inebriated and everyone seemed to enjoy themselves.

The people started to drift off home in the wee hours of the morning and the last person to leave was Mrs T. She didn't have far to go and she appeared to be very drunk. Ben, Jay's father, and Gail, Jay's mother, started to tidy up as Jay chatted to Mrs T.

"I'll help with that." said Jay.

"No. No. No." said Ben. "It's your party. You relax and enjoy it."

"It was a great party, dad." said Jay. "Thanks to both of you for throwing it for me."

"You're welcome, Jay." said Gail. "You're only 21 once."

"Did you get some lovely presents, Jay?" asked Mrs T.

"I sure did, Mrs T, and thanks for the book. I'll have something to read during the summer holidays." answered Jay.

"You're welcome, Jay." said Mrs T. "Maybe I'll borrow the book when you're finished reading it?"

"Of course." said Jay. "I'll bring it over when I'm done."

Ben took away the empty cans and bottles in front of Jay and Mrs T. Mrs T said "I'm still using that one, Benny." as she picked up her wine glass.

Mrs T spun on the bar-stool and said "Where'd everyone go? Oh... I guess it's time for me to leave." She downed the remainder of her wine and attempted to stand up as she said "I'll pick that up on the weekend." and pointed to the wine-cask still on the bar.

Jay steadied Mrs T as she slipped off the bar-stool. "Thanks, Jay." slurred Mrs T. "I might have drunk a little bit more than I intended."

Gail said, "Jay, make sure Sandy gets home safely."

"Okay, Mum," said Jay, as he steadied Mrs T.

"I'm okay." said Mrs T. "It's just across the lane. Nobody 'ill be driving on that."

"Nevertheless...." said Gail and Jay knew that he was not going to avoid the allocated task.

Jay wasn't as drunk as Mrs T: his preferred poison was cannabis and had slipped out for a few joints with his friends during the night. He did drink a few alcoholic drinks, to keep up appearances for his parents, and the dope accentuated the affects of the alcohol, so he was inebriated, but not as much as Mrs T appeared to be.

Jay helped Mrs T as they laughed all the way down the front steps. She winced as she stepped onto the asphalt. "I should have brought some thongs." said Mrs T, as she stepped back onto the relatively smooth concrete.

"Come on Mrs T." said Jay. "I'll give you a piggyback across the lane."

"No. No. No." said Mrs T. "I probably won't feel a thing." but then winced again as she attempted to cross the lane.

"On you get Mrs T." said Jay, as he turned his back to her and squatted.

"I'm too heavy, Jay." said Mrs T as she, again, failed to negotiate the rough road.

Jay backed into Mrs T and Mrs T grabbed his shoulders to stop herself from falling over. "Okay, you win." said Mrs T, as she climbed onto Jay's back.

"Ride 'em cowboy!" called Mrs T, as she tried to slap Jay on his bum.

Jay wasn't as steady on his feet as he thought he would be, but managed to safely cross the lane. Mrs T whooped and laughed all the way across the lane.

"Whoohoo!" cried Mrs T, when they made it to her lawn. She tried to stand up on Jays back. Jay lost his balance and they both toppled onto Mrs T's soft, spongy lawn.

Mrs T was cackling with laughter. Jay was also having a good chuckle. Jay managed to ask "Are you okay, Mrs T?"

"Never felt better." answered Mrs T, in-between bouts of laughter.

Jay noticed that Mrs T's top had shifted during the fall and her right breast was exposed out of the bottom of her tube top. Jay stared at Mrs T's breast, but then pulled her top over her breast. Mrs T looked at what Jay was doing and said "Oops, I've popped out." and they both laughed.

Jay managed to steer them both to Mrs T's front door. He held out his hand and chuckled "Key please."

"Oh yeah..." said Mrs T, as she searched around her crotch. "Oh, it's moved..." and kept searching. "Here it is." she said, and held up a single key. She wiped the key on her nappy and said "You don't want to touch that." and then handed the key to Jay.

Jay laughed with Mrs T, but then thought that he probably would like to touch it after where it had apparently been.

Jay opened the front door, helped Mrs T through to her lounge room and said "Make sure you lock the door Mrs T."

Mrs T locked the door with Jay still inside and they both laughed when they realised her mistake.

Mrs T suddenly stopped laughing and Jay laughed at the shocked look on her face. Mrs T bit her bottom lip and joined in laughing. She said "I think I've peed myself."

Jay laughed even more and Mrs T said, in-between bouts of laughter, "No, no, I think I really have."

Jay laughed and said "Well lucky that you're wearing a nappy."

Mrs T laughed and said "Yeah, it is isn't it." She looked at her legs and added "It seems to be working."

Jay laughed louder and so did Mrs T.

"This way Mrs T." said Jay, as he guided her upstairs to her bedroom.

"Don't call me Mrs T, Jay. You're a man now and it makes me feel old." said Mrs T, as she stumbled through her bedroom doorway.

"What shall I call you?" asked Jay.

"Alexandra's my name, but it's a mouthful like this pacifier." said Mrs T, as she put the huge pacifier into her mouth. Her eyes started to water and she pulled out the dummy with a cough. "I think I'm going to be sick." she said, then she rushed into the en suite and vomited into the toilet.

Jay rinsed a face washer and wiped Mrs T's face. He asked "Are you okay?"

"I'm sorry you had to see that, Jay." said Mrs T. "Thanks for taking care of me."

"I guess you had a gag reflex, Mrs T." said Jay, as he kept cleaning up the mess she'd made.

"It's never been a problem before." said Mrs T. "I think it might be the booze."

"Could be." laughed Jay. "Let's get you to bed Mrs T."

"I said don't call me that." said Mrs T.

"Okay, then tell what name should I call you?" asked Jay.

"I've been called many things: Alessandra, Al, Sandra, Sandy, Les, Lesbo Les...." said Mrs T, but then she put her hand over her mouth. "Don't tell your parents that last one."

"I won't, but I'll tell all my friends." said Jay, with laughter.

"No, please don't, Jay." begged Mrs T.

"It'll be our secret... Les." said Jay and laughed.

"You can't call me that, especially, in front of your parents." said Mrs T. "Call me, Sandy."

"Okay, Sandy." said Jay, still laughing. "Into bed with you."

"With me?" asked Sandy and then chuckled.

"No. Just you, Sandy." answered Jay, still laughing.

"I need to wee." said Sandy, and struggled with the huge safety-pin at the front of her nappy.

"I thought that you said you'd already wet yourself?" asked Jay and laughed.

"I did, but I need to finish." said Sandy. "Help me with this please, Jay."

Jay easily undid the safety-pin and Sandy's nappy fell off revealing a wet pair of white, high-waisted, cottontail undies. Jay saw Sandy's matted pubic hair under the translucent material and he said "I'll wait outside."

"Thanks, Jay." said Sandy.

Jay heard Sandy urinating into the toilet and started to get a semi. He heard the toilet flush and wondered what Sandy would be wearing as she came out of the en suite. He waited and saw Sandy struggle through the doorway with a bath towel wrapped around her waist.

Sandy fell into bed. Jay put a glass of water on her bedside table. He said "Good night, Sandy."

Sandy said, "Good night, Jay. And thanks for helping me. I'm sorry you had to see... um, all that."

"You're welcome, Sandy." said Jay. "And don't worry about any of it. Mum's the word."

Jay went home. As he was getting into bed, he saw that Sandy's bedroom light was still on. He called Sandy.

"Hello?" answered Sandy, when she sleepily answered the phone next to her bed.

"Sandy, it's Jay." said Jay "Turn off your light."

"Oh yeah." said Sandy and hung up. Jay watched Sandy's bedroom window until he saw her light extinguish. He then went to sleep.

~~~

The next day, unsurprisingly, they all had hangovers.

Gail said to Jay, during breakfast, "Jay, could you please check on Sandy?"

Jay knocked on Sandy's door. He became worried when it took Sandy so long to answer the door. Sandy slowly opened the door dressed in a short, silk dressing gown.

"I was worried when you didn't answer the door." said Jay.

"Why?" asked Sandy.

"I thought that you might have drowned in your vomit." answered Jay.

"Oh yuck!" said Sandy. "I feel bad enough without hearing that lovely description."

Sandy made herself a Berocca drink and offered Jay one. Jay accepted and they sat at the dining table to slowly drink their Beroccas.

"That was a good party, Jay." said Sandy.

"Yeah. I think everyone enjoyed themselves." said Jay. "You looked fantastic in your baby costume."

"I didn't know what to wear. I'd forgotten that it was fancy dress." said Sandy. "I thought to just put on that short top, the nappy over my undies, the silly bonnet and the big dummy."

"Where'd you get that dummy?" asked Jay.

"I bought it as a joke to throw onto the floor whenever Mark chucked a tantrum." answered Sandy. "Sort of 'spit the dummy'."

Jay laughed and Sandy joined in.

Jay watched Sandy's breasts jiggle, under her dressing gown, as she chuckled.

Sandy saw him looking and he was embarrassed, she smiled and said "You were Jesus Christ weren't you?"

"Yes." answered Jay.

"The crown of thorns gave it away." said Sandy.

"I didn't offend you did I?" asked Jay.

"No. I'm not religious," answered Sandy "but I might have offended some people with my costume."

"Not at all." said Jay. "Lots of my friends asked me who was the sexy baby."

"Oh rubbish." chuckled Sandy. "You don't normally lie, Jay."

"No it's true." said Jay.

"I'm old enough to be their mother." said Sandy.

"You still looked sexy." said Jay.

Sandy looked at him. She pulled her dressing gown closer around her. She asked "What did you tell them?"

"Pardon?" asked Jay.

"Who did you say the sexy baby was?" asked Sandy.

"Mrs T, my next door neighbour." answered Jay.

"Oh Jay." said Sandy. "That makes me sound so old."

"Sorry." said Jay.

"Thanks for helping me home last night." said Sandy.

"You're welcome." answered Jay.

"Thanks for... for covering me up." said Sandy shyly.

"When was that?" asked Jay.

"On the lawn..." said Sandy. "When my... um... when... I... sort of... fell out."

"You're welcome." said Jay, feeling a twitch in his penis as he remembered Sandy"s breast.

"You're a gentleman, Jay." said Sandy.

Jay laughed, mockingly, "Yeah."

"You are." reaffirmed Sandy.

"A lot of good that does me." said Jay.

Sandy reached across the table and held Jays hand. "Women appreciate a gentleman." said Sandy. As she leant forward, her dressing gown opened sightly. Jay could see part of her breast. He swallowed. He looked at her eyes. He could see that she knew that he was looking at her chest.

Sandy sat back, but didn't adjust her gown. They sat like that for a while in silence. Jay kept looking at Sandy's breast. She smiled when he looked into her eyes.

"You're a good bo... man... Jay." said Sandy, with a smile.

"You were going to say 'a good boy'." said Jay.

"Well, I've known you since you were a baby, so it's... it's taking a while for me to adjust to you being a man, Jay." said Sandy.

Jay sighed.

Sandy leant forward again. He could definitely see one nipple and the areola of the other. She said "One day, you'll make a woman very happy, Jay."

"I hope it's more often than just one day" said Jay.

Sandy laughed.

Jay watched Sandy's breasts jiggle, as she laughed.

Sandy looked at her chest to see what Jay was looking at. She said "Oh I've seemed to have... popped out again." She didn't cover herself up until she looked into Jays eyes and said "Sorry."

"That's quite alright." said Jay. "I don't mind at all."

"You shouldn't have to put up with seeing a woman's breasts who's old enough to be your mother." said Sandy.

"You have beautiful breasts, Sandy." said Jay.

Sandy cupped her breasts, looked at them and asked "Do you really think so?"

"Yes, they're very beautiful" answered Jay, as he watched Sandy's breasts jiggle in her hands.

"I'd better put them away then." said Sandy. "I don't want to tease you... too much."

Sandy looked directly into Jay"s eyes as she, first, slowly tucked one breast, and then the other into her dressing gown.

Jay stood up and said "I'd better get going." He noticed Sandy looking at his crotch, which was bulging due to his erection.

"How did you know my light was on?" asked Sandy, as she followed him to her front door.

"When?" asked Jay.

"Last night." answered Sandy. "After your birthday party."

"I saw your light through my bedroom window." answered Jay.

"Wait." said Sandy. She leaned forward again, feigning interest, but also revealing her breasts "You can see my bedroom window from yours?"

"Yes." answered Jay, as he watched her breasts.

"Can you see my window from any other part of your home?" asked Sandy.

"No." answered Jay. "The other windows are oriented towards the view. Mine only has a view across the lane, to you home."

"What else can you see of my home from your bedroom window?" asked Sandy.

"Your backyard and balcony." answered Jay.

"I thought it was all quite private." said Sandy.

"It is." said Jay. "I think that my window is the only one from where anyone can see those places."

"I see. Do you sleep with your curtains open?" asked Sandy.

"Sometimes." answered Jay, wondering to where this change of tack was leading.

Sandy smiled coyly and said, "Sleep well, Jay." as he left.

That night, Jay had switched of his bedroom light and left his curtains open.

Later on, he saw Sandy's bedroom light turn on. He watched her do something in the en suite. She approached the curtains, but she didn't close them. He watched her take off her blouse, skirt and bra. She caressed her breasts in front of the window. She pulled her nipples. She wiggled her breasts as she raised her arms to hold the curtains. She posed like that for a moment, staring out towards Jay. She then closed her curtains.

Jay closed his curtains and masturbated.

~~~

They saw each other over the following weeks. Jay wondered if Sandy was wearing more casual, if not, more revealing clothes.

Sandy would often have lunch with Jay"s family on nicer Sundays. Especially since Mark, Sandy's late husband, had died. Sandy would bring a salad and Ben would cook some meat dish on the barbecue.

One Sunday, they were at Jay"s home. He and Sandy were alone on the balcony as Gail was getting them drinks and Ben was cooking lunch on the barbecue. Sandy leant forward. The front of her dress fell forward and Jay could see the tops of her breasts.

Sandy stretched her arms over her head and yawned. When she rested her arms on the table Jay could see more of her breasts. In fact, he thought he could see her areolae. She leant further forward, and Jay could definitely see her nipples. She smiled from behind her sunglasses and asked "Are you enjoying yourself?" She sat back in her seat when Gail arrived with their drinks. Her breasts were completely covered again by her dress.

"Jay," asked Sandy "do you have a hat that I could borrow? It's getting a bit sunny here."

Jay had an erection and didn't want to stand up.

"I'll get you one of mine." said Gail.

"No, it's alright." said Sandy, staring at Jay. "Jay's a gentleman, you'll get me a hat won't you, Jay?"

Jay stood up. Fortunately, his napkin was still tucked into his belt to, hopefully, hide his erection. He smiled at Sandy, went inside and returned with a hat for her, who put it on. "Thank you Jay." said Sandy "You're a good, man."

Jay couldn't help but notice that Sandy remembered to call him a man.

Jay sat down opposite Sandy to eat his lunch. Moments later, he felt a foot touching his leg. He looked at Sandy, who was concentrating on a discussion with Ben. Jay felt the foot slide up his calf and push between his knees. He watched Sandy and was impressed at how she seemed absorbed in their conversation, yet was caressing his thighs with her foot. She stopped her foot, half way along Jay's thigh, so he spread his legs and her foot continued towards his crotch.

Jay felt Sandy's toes searching his lower body and then wiggle when they found his erection. Jay looked at his mother, hoping that Sandy was watching how cool he was with the situation. He wondered what his mother would do if she knew Sandy was stroking his erection with her toes.

Jay finished his food and leant back in his chair, pressing his erection against Sandy's foot. She looked at him, so he smiled at her and she smile back. She then continued with the conversation.

Jay could feel pre-ejaculate leaking from his glans.

"Help clear the table please, Jay." said Gail.

"I'll help." said Sandy. "I need to go to the ladies."

Jay was relieved that he didn't have to stand up and, consequently, expose his bulging, and possibly wet, crotch to his parents.

~~~

Over the following weeks, Jay saw Sandy exhibiting her breasts to him from her bedroom window. She was some sort of exhibitionist. She even exposed her bottom to him as she bent forwards to take off her underpants. He saw a wisp of pubic hair, silhouetted by the bedroom light.

Another time, he saw her breasts as she laid sunbathing on the balcony in just her bikini bottoms. He loved how she surreptitiously exposed herself to him, even though it was from a distance. Sandy was definitely his major masturbatory influence.

At one Sunday lunch, when they were alone on the balcony, Sandy asked "Do you smoke?"

"No." answered Jay.

"I mean... dope?" asked Sandy.

Jay sat in silence.

"Don't worry. I won't tell." said Sandy. "It'll be our little secret."

"Like Lesbo Les?" asked Jay.

"Yes." answered Sandy, who seemed a little self-conscious. "You haven't told anyone about that, have you?"

"Of course not." answered Jay.

"Thank you." said Sandy. "Your a good man, Jay.