Love With A Fit Grandmother

Tony was a lovely man; he was 63 and slightly overweight. He was married for 20 years but lost his wife 10 years ago. They had met on the cruise ships where Tony worked as an entertainer and his wife was a dancer.

They returned home a couple of years before she passed, so Tony’s wife could be near their family at the end.


Tony’s friend Ron got him a job in his limousine company cleaning and maintaining the cars with Tony eventually working his way up to driving the cars.

Tony arrived at work on Wednesday to check what his jobs were for the weekend.

Friday – bachelorette party in the name of Perry.

Saturday – prom in the name of Sullivan.

“Oh no bachelorette and prom in the same weekend” Tony didn’t like either of them. Bachelorettes were always loud and drunk, While proms were normally arrogant 18 year olds. Tony loved weddings the most. Taking the bride and the bride’s father or mother to the wedding. He loved the happiness and ceremony of it all.

Friday’s bachelorette party was its usual loud, drunk women having too much to drink and being sick shouted lewd remarks towards Tony he always thought it was funny that a week or two later they would be dressed in white looking angelic. He admits that its very tempting but he always stayed professional.

Tony spent Saturday morning cleaning out the sick and spilled drink from last night’s bachelorette party so it was ready for the prom booking later.

Tony left the depot about 6 for the prom pick up. He put the address in the sat nav. It was going to be a 25 minute journey, so he put some Elvis Presley on and started his journey.

Tony pulled up to a large house painted blue and white. He knocked on the front door and a very attractive older woman answered.

“Hi madam my name is Tony I’m here for miss Heidi Sullivan.”

“Good evening I’m Judy I’m Heidi’s grandmother.”

Tony was taken back. This woman didn’t look old enough to be a Grandmother.

“Nice to meet you Judy I will be by the car when Heidi is ready”

Tony turned as he heard the front door open and out stepped three beautiful women. They took lots of photos to put on Facebook or something like that.

“Hi, my mother says your name is Tony. I’m Vivian Heidi’s mother.”

“How do you do Madam”

“This is my daughter Heidi”

Standing there was the most beautiful young girl with long brown hair and in a gorgeous blue silk dress.

“Hi sir I’m Heidi”

“Good evening madam your carriage awaits”

Tony said as he moved to the limo door and held it open for Heidi to climb in.

Tony then turned to Heidi’s mother and grandmother.

“Lovely to meet you both and try not to worry about Heidi she will be fine.”

“Back by midnight” Heidi’s mother said with a tear in her eye.

“I have to be back by midnight or I’ll turn into a pumpkin,” Tony joked.

Tony got in the car and his Elvis Presley music was still playing.

“Sorry madam I will turn my music off”

“It’s ok Elvis is my dad’s favourite. And please call me Heidi.”

“Ok Heidi I’m Tony, I didn’t see your dad tonight”

“He is in the US Air Force so is away a lot. But I Skyped him earlier”

“I bet he’s gutted to miss his daughter’s prom.”

“Yes he was and I really missed him tonight.”

Tony and Heidi spoke all the way to the school hall where the prom was being held. Tony told Heidi about his career on the cruise ships and how he met the love of his life. Heidi spoke about how lucky she is to live with two strong women and her boyfriend Todd who she was meeting at the prom.

The car pulled up at the school and Tony opened the door helping Heidi out the car.

“Thank you Tony so much”

“My pleasure Heidi and i will see you later. Can you see your date?”

“Yes he’s over there, OK Tony see you later”

Tony went and grabbed a coffee from a coffee shop down the road and drank it in his car listening to Elvis. Tony finishes his coffee and crushes the cup before throwing the crushed cup into a nearby trash can.

Tony hears a commotion from outside the school entrance.

“Go to hell Todd”

“Lighten up Heidi there is plenty more where you come.”

Heidi runs to the car crying and shivering

“Are you OK, Miss Heidi?” Tony asks worryingly while slipping his tuxedo jacket around Heidi’s cold shoulders. Heidi gets in the limo and slams the door and Tony pulls away heading for Heidi’s home.

“Don’t cry Heidi it can’t be that bad”

“It is Tony I found out that Todd had a bet with his friends that he would sleep with me tonight”

“Oh I’m so sorry Heidi but that is boys for you, please give me your home phone number so I call ahead to explain to your mother what’s happened and I am bringing you home early.”

Heidi gave Tony the number and he called through the Bluetooth, explaining to Vivian they were on their way back and he wasn’t sure what had happened. He thought Heidi should tell her.

“Are you OK now Heidi”

“Yes thank you Tony.”

“You can talk to me if you want”

“The thing is I feel very comfortable talking to you, like I’m talking to my grandpa.”

“Well I am very honoured”

“Thing is Tony I tried sex once and I didn’t like it and hated myself after. I vowed the next time would be someone who didn’t see me as a trophy”

“Good for you, the right young man will come into your life. Until then carry with that philosophy.”

Tony and Heidi talked all the way back to the house and Tony cracked some jokes which Heidi didn’t get but still laughed. They eventually reached the house where Heidi’s mother and grandmother were standing outside looking concerned.

Heidi’s mom had the door open as soon as the limo stopped.

“Are you alright my darling? What did that idiot Todd do to you?”

“I’m fine thanks mom. I don’t want to talk about it now.”

Heidi and her mom made their way into the house as Heidi’s grandmother Judy made her way over to Tony.

“Thank you Tony, you’re a very kind gentleman.”

“That’s Ok Judy. Heidi is a very special young lady and a credit to you all. Go in now Judy and spend time with your granddaughter.”

“Thanks again Tony, be safe.”

Judy turns and goes back to the house. Tony then remembered that Heidi had his jacket, never mind he thought I have another at home.

Tony returned the limo to the depot and left for home. He got home earlier than expected so poured himself a whiskey and started watching an old movie.

Tony returned to work on Thursday to get his limo prepared for the weekend.

“Hi there Tony, how are you?”

Tony turns to see Heidi’s grandmother Judy standing there.

“Hello Judy, what are you doing here? It’s great to see you.”

“I had your jacket dry cleaned and I’m just returning it to you. I came in on Tuesday and your friend said you would be here today.”

“How lovely thanks, I’m nearly done here if you fancy having lunch with me Judy.”

“That would be lovely Tony.”

“Ok Judy please give me 10 minutes.”

Tony and Judy made their way to a little Italian bistro that Tony knew. They shared a bottle of red wine and a three course lunch. Tony spoke about his wife and how difficult and lonely it was for a few years after her death and how getting back to work brought him back to reality.

“You must love your job Tony”

“I do get to meet some interesting people.”

“And you got to meet me and my family”

“That’s a good part of the job, meeting good people like you. You haven’t told me about your husband Judy, how long you were married.”

“Oh Richard, he was a good man. He was a stockbroker in New York.”

“You lived in New York.”

“Yes unfortunately he was near the top of the North tower on 9/11 and he didn’t make it out.”

“I moved out of New York with my daughter just after. New York suddenly felt a huge place”

“Oh Judy I’m so sorry.”

“We go back on the anniversary and pay our respects.” She replies with a tear running down her face.

Tony passes Judy a tissue and rubs her hand for comfort.

“We have both seen heartache, Judy. Perhaps we need some love in our lives.”

Judy didn’t know why she leant in for a kiss and Tony followed and kissed gently on the lips then pulled away.

They spent the afternoon walking around town looking in antiques stores laughing and giggling like they had known each other all their lives. It was about six o’clock and they had lost track of time.

Tony hailed Judy a taxi.

“I have to get Tony back but I’ve had a great day. Maybe we could do it again.”

“Would you like to come to mine for dinner on Sunday? I only have a modest house but I’m a great cook.” Tony asked hopefully.

“I don’t care what your house is like, I would love to have dinner with you. About 7 alright.”

“Brilliant, I will give you my address.”

Tony pulled out a business card with his number and address on and passed it to Judy.

As he said bye he kissed Judy again, Judy kissed back this time lingering and slightly open mouthed.

“See you Sunday Tony” She said as she got into the taxi and headed home.

Friday and Saturday nights shifts couldn’t pass quick enough for Tony. At least he had a wedding Saturday which he always enjoyed.

“What to cook” Tony said as he scoured the Sunday morning Market for something to cook for his date with Judy.

“You idiot, why didn’t you ask if she was vegetarian, vegan or if she allergens you Idiot” other people looked at Tony like he was mad.

Tony thought of calling Vivian or Heidi, he still had their number in his phone. But he remembered Judy didn’t want to know about their date yet.

“Eureka” Tony screamed suddenly, convincing everyone around that he was insane. He remembered the lunch he had with Judy. He just had to remember what she had ordered

But he couldn’t, He checked his wallet and found the receipt.

“Yes, I got it chicken carbonara.”

Tony picked up the ingredients for chicken carbonara from a recipe he found online.

Tony looked at the clock. It was 10 mins to 6 and the carbonara was bubbling slowly in the oven on a low heat with just the pasta to cook later. The table was set and the red wine was in the decanter. Ok time for a shower and spruce himself up.

Tony got dressed into a new shirt and trousers and splashed on a bit of aftershave. He was getting very nervous now. What if she doesn’t like the food, doesn’t like me and what if she stands me up. He was so jittery he poured himself a whiskey and drank it straight down.

At 5 past 7 there was a knock at the door Tony opened it slowly and standing there was a vision of beauty, Judy looked amazing and 20 years younger, she was wearing a blue skirt and blazer with a striking pink silk t shirt underneath and her blonde with a slight hint of grey hair was up at the back with a few strands falling down her face.

“You look absolutely divine Judy so beautiful”

“You scrub up as well Tony”

“Can I take you Jacket Judy”

“Yes of course.”

As Judy slipped out of her jacket Tony couldn’t help to notice her curves and how firm her body looked. She had a body of a much younger woman, not somebody who was on the wrong side of 50.

“Would you like a glass of wine Judy, is red ok.”

“Yes, red is fine but can I have a kiss first?”

Tony moved in for a kiss nervously and placed his hands on Judy’s arms. They kissed for a couple of minutes neither one of them wanted to pull away, their tongues occasionally touching. Tony pulled away still rubbing his hands down Judy’s arms.

“I better check the dinner.”

“Smells delicious Tony what is it”

“Chicken carbonara I remembered you ate it at our lunch date”

“How good of you to remember.”

Tony served the food, they ate and drank reminiscing about the old days and how smaller and expensive things had got. After dessert Tony cleared up.

“Do you like to dance Tony”

“I love too, my wife was a Latin and ballroom dancer she was amazing”

“I love to salsa but I’m too full after that dinner how about a slow dance”

“I would love to.” Tony only just managed to get his words out as he made his way to the stereo.

Love me tender by Elvis played as the two started to dance. Judy placed her arms around Tony’s neck while kicking off her shoes, Tony placing his hands on the small of Judy’s back. As their bodies Tony felt Judy’s breasts press against him they felt amazingly firm but just soft enough to spread as they hit his chest.

As they danced passion slowly started to build. Tony now one hand inside the back of Judy’s silk t-shirt gently stroking her back while gently kissing her neck. Judy’s small hairs were standing up as she felt Tony’s breath and lips on her neck. She pulled Tony’s shirt off over his head and started kissing his neck and chest. They were not dancing anymore.

Tony took Judy’s silk shirt off exposing a well filled satin bra which Judy unclipped and dropped to floor. For a woman of nearly 60 her breasts were amazingly firm with just a touch of softness and generous 36e in size.

Tony pulled Judy’s head from his chest and started kissing her breasts carefully caressing the nipples with his tongue. Judy was in heaven as stroked her fingers down Tony’s back. Tony continued to caress Judy’s breasts slowly flicking the nipple with his tongue. Judy had not experienced an orgasm for a long time as she felt a shiver through her body and a wetness down below.

“Let’s go to bed,” Judy breathlessly whispered to Tony.

Tony smiled back “are you sure”

“Please, I want to make love. It’s been so long.”

Tony smiled again, held her hand and led her upstairs.

Tony allowed Judy to enter his bedroom first and then stood behind and pulled her to him with her back to him. Tony gently kissed the back neck then moving to her ears, his hands were softly squeezing her breasts Judy could feel the hairs on Tony’s round belly tickling her back. His hand moved from her breast and down her stomach Tony stroked her soft skin running a finger over her belly button before stopping at Judy’s vagina which rubbed over her skirt. He gently squeezed it, sending Judy’s head backwards with her eyes closed with pure pleasure on her face.

Judy moved to the edge of the bed and sat on it. She put her hand on Tony’s waistband and pulled him towards her kissing his stomach leading down to his crotch. Judy undone Tony’s trousers and pulled them down to his ankles. She could see his erect penis poking through his briefs which she also pulled down leaving Judy staring at Tony’s erection of 7 or 8 inches.

Tony groaned with pleasure as Judy started running her tongue around the end of his penis stroking his testicles with her free hand. Judy moved down the shaft kissing it every now and again giving it a little lick then moving back to the top of penis and taking it in her mouth. Tony pulled the pin from Judy’s blonde with a little grey hair and it dropped just below her shoulders. Tony ran his fingers through it as Judy continued to caress his penis with her mouth. Her hair was so soft and smelled like a forest.

Tony gently moved Judy’s head away from his penis and lay her on the bed. He kissed Judy on the neck moving down kissing and licking every part of breasts and upper torso. Judy gently lifted her bottom off the bed so Tony could pull her skirt and panties off. Tony moved down to her thighs kissing them and licking them then he moved to her vagina and he kissed it driving a surging feeling through Judy’s body. He slowly placed a finger inside Judy as he kissed and licked her red cherry.

“Oh my god” cried Judy.

Tony moved his body between Judy’s legs. Her legs were so firm from the Pilates she attends once a week. Judy puts her hands on the back of his neck and pulls Tony in for a kiss.

Tony gently inserts his penis inside Judy’s vagina making her give a little moan as he gently moves his hips backwards and forwards. Judy is close to orgasm again as Tony’s penis slowly penetrates her. Tony picks up the pace and the pair’s bodies are now hot and sweaty Tony is now going at quite a quick pace but not pushing his penis too hard out of his respect for Judy. Judy’s blue eyes are wide open with pleasure as Tony’s penis does its work.

“Sorry Judy I’m about to cum” Tony whispers as he pulls out of Judy placing his penis on Judy’s public area. Judy whispers “ok”

As she reaches down and grabs Tony’s penis slowly wanking him, Tony kisses her breasts and then they kiss. Tony can feel he is close as Judy continues wanking him. Then with a groan Tony cums shooting his seed on Judy’s soft skinned stomach and on the bottom of the breasts They kiss again and just hold each other Tony’s cum squashed on both their bodies.

“Judy that was amazing thank you”

“No, thank you Tony I never thought I would feel like that again”

“You are so beautiful, your body and breasts are incredible and feels like a woman half your age”

“Oh Tony you know exactly what to say to make a woman feel good”

“I meant all of it and I would love to see you again”

“Goes without saying I want to see you again as well.”

Tony and Judy shower and afterwards enjoy another glass of wine. It was getting late and both were tired

“Would you like me to call you a taxi Judy”

“It’s ok Tony I don’t need one I was hoping to stay the night”

“That would be lovely but are you sure”

Well I bought this with me just in case” as Judy pulls a tooth brush out of her bag.

Tony smiles at her then leads her back to bed where they make love again.

Tony and Judy’s romance was going strong weeks later and their love making got more adventurous. Judy suggested it was time to tell Vivian and Heidi so arranged a dinner at Vivian’s House.

“Who is it grandma?” said Heidi impatiently.

Vivian was also getting impatient as they waited to see who the man was that had made Judy happy as she’s been in years.

The bell rings as Tony arrives at Judy’s house; he stands there as Vivian and Heidi open the door.

“Oh my god Tony it’s you I am so happy for you and my grandma.”

“Thank you miss Heidi and good evening to you Vivian.”

“Good Evening Tony, come in.”

Tony closed the door as he began the next chapter of his life.



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