Bob, Sue and Anita's Romance Pt. 01

Dear Reader, hopefully you will enjoy my story on Literotica so I can post more.

I am happy to receive comments and PMs. I welcome constructive criticism.

Thanks to Mfan and others for helping proof read.

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Do you know what is good about being old? You don't have to worry about what people think of you. After nearly thirty years of marriage, there isn't that pressure to perform, or even try to impress or obtain results from new relationships.

This confidence of his age had brought Bob to this cheap busy beachside pop up bar, plus it gave a superb view across the beach. He had chosen a quiet stool position to sit alone high up at a shallow table window cill, on the short side of the 'L' shaped inside-bar. This view included the groups of millennials partying on the veranda below. So whilst up out of the noise, hustle, and bustle he could still crowd watch, soaking up their atmosphere whilst also quietly sip a beer, check emails, texts, and Facebook posts on his old smartphone.

Bob was quietly enjoying himself. There were still surfers out in the waves, families on the beach for a late walk, and dog walkers. He could work out the top dog drinkers, players, dancers, and romancers in the lads drinking below, plus the girls, all exhibiting traits he and his mates all had seen and experienced in the past.

Slightly jealous of the young 20 something lads, maybe a little relieved, no longer having the pressures of performing to impress mates or to court girls, although unlike them Bob had never had a real holiday romance in all his 55 years, he lamented.

A woman brushed passed behind him, squeezing into the even more isolated spot in the corner, against the wall on his left. Bob looked round to smile. She was a nice thin build, wore a nice close-fitting black T-shirt, with a short yellow platted summer skirt hanging over a nice tight bum.

She rested her soft drink and mobile phone down on the far end of the window cill, propping herself on the last stool. She avoided any eye contact, her red hair with purple gloss highlights draped over black-rimmed glasses, hiding her eyes. Once settled, she didn't pay any attention to the scene, she just looked down and scrolled through her phone screen.

She appeared to be in her early twenties, her pert breasts not overly large but nice, trying to burst their way out of her tight T-shirt. Bob would have liked to have guessed their size, but he didn't even know his wife's bra size, so had no gauge to compare them against.

Bob's attention returned to his drink, the view, and a tall blond who had just appeared into view, walking her little dog down the road to the beach. She was wearing those long gym pants that showed off a pert pair of buttocks and lovely athletic legs.

After a short while, Bob heard a stifled sob to his left. He glanced across to confirm it was the woman sat in the corner. At first, he ignored it, as she obviously didn't want to interact with anyone. But after the third stifled bubble sob, he felt he should say something.

She now had her head in her hands, murmuring to herself, in a whisper that Bob couldn't hear. Her tone was anger towards herself. He caught the odd "Why..." and "Again."

"Hi, I'm Bob, are you ok? Lovely weather we're having." Bob just couldn't resist trying to improve his evening with a little light conversation with a young woman and hopefully improve hers too.

As a young man, Bob couldn't talk to pretty girls, his tongue would just get in the way; he could barely blurt out a few words in fear, let alone a full sentence. Now at his age, he just had to think and words just tumbled out.

She turned with a scolding look, her breasts swung slightly, showing she was bra-less. Bob tried to keep his eyes upwards on her face; he could just see her eyes burning through her overhanging fringe.

Her glasses that were the type you expect teachers or white lab coat wearing scientists in makeup adverts to wear. They sat on a lovely button nose, with nose and cheeks speckled with freckles that confirmed she was a genuine redhead.

Anita was used to being pestered, and usually, she enjoyed the attention, although tonight was the exception as she wanted to be left alone in her thoughts. But she was also used to living in the moment, taking what was in front of her as she didn't have any real long-term friends. So she was used to adapting to new friendships, just like switching television channels, to chase the next relationship fix, no matter how shallow or superfluous.

Her temperament changed and relaxed as soon as she caught sight of him, Bob seemed that perfect safe non-threatening channel surf to pause on and see if the program was worth watching.

Bob interpreted that softening in her glare as an opportunity to continue, "Sorry, that was my best chat up line, if you want to talk, happy to. You don't have to tell me your troubles, but with me being a stranger I will be none the wiser and you will know your secrets will be safe with me. Or we could just gossip about Mr. Red Shirt down there, that is mad about his best mate Mr. Liverpool shirt and not his girlfriend?" Bob persevered.

She blurted out a stifled laugh, brushed her fringe back, and looked down to the veranda, trying to find "Mr. Red Shirt".

Bob held his right hand out to her, "Shall we start again, Hi I'm Bob "

She turned to him, brushing her hair back to uncover her face, smiled, with tears still dribbling down her face, "Hi I'm Anita" she sniffed, grabbed a napkin off the table, and wiped her face dry, and blew her nose.

She held her hand out, and they lightly shook. She had soft cool hands compared to Bob's big rough builder's hands. She even smiled Bob thought she was a lovely pretty twenty-something.

"He's down there on the right with a girl in a yellow top seems to be with him, but he is touching his mate at every opportunity. He would rather ravage Mr. Liverpool shirt before Miss yellow dress," explained Bob.

Anita stifled a sniff and laughed lightly. "You must be a relationship expert," she sarcastically quipped.

"That I am, brilliant with other people's relationships, knowing all, always right, but never with my own, I am useless at that, or so the wife tells me," said Bob.

Then angrily to himself, `For fuck's sake bob, first chance to talk to some lovely bird and you mention the wife - you've just given her a cold shower'.

"So you're married, where is she tonight?" asked Anita, pulling her stool closer, Bob seeing that as approval.

"6 foot under the patio back home, no that's the ex." Bob joked, hoping to lighten the conversation. "No, honestly, she is suffering from a terrible migraine. They often keep her bedridden suffering for two to three days. So I am kicking my heels on my own for a few days."

"So, do you want to talk about your bad news?" Bob pressed.

Anita looked back at Bob and smiled, "As it's you and you may do me a deal on a patio," her eyes sparkled.

Bob laughed, and she blushed and explained. "My latest failure of a long line of failures, I thought this was it after several months and for once I had a relationship, someone who loved me for what I am, but she arranged for her ex-boyfriend to just happen to be here with his mates and tried to get me involved. So I kicked her out of the holiday flat yesterday. That was a text dumping me and assassinating me with all my traits and bad habits."

"She?" blurted Bob, "Oh, sorry," whilst not completely ignorant of modern sexuality, he was still shocked to find such a beauty as this to be a lesbian. Not his archetypical picture of a butch, man-hating bearded lady, but the stunning one sat next to him having a conversation.

"Well, I am Bi-sexual, I love both genders and a few in between," she smiled, wondering if she could tease the player in Bob out into the open, to expose any hidden desires and possibly change the course of the evening, she then whispered, "But I do love a good stiff cock," giving Bob a wry smile.

Now it was Bob's turn to blush. Although, after a lifetime of mixing with extrovert bikers, this comment wasn't untoward or out of character for some of his friends. But it stirred his dick with just the thought of it.

"Haha, I am getting better at this," she blurted & smiled with a quizzical look, leaving Bob not exactly sure if she had joked or not.

Bob had nearly finished his drink, drained it, and lifted the empty glass to offer, "Would you like to join me with one?"

"I wasn't going to," she raised her soft drink to show him. "I'm not a big drinker, in the past, it has led down bad paths that I am trying not to go down again, but as it is you and I am feeling happier, thanks, I'll have a Bombay gin and tonic," she beamed in reply.

Bob got up and went to the long end of the bar, got the bartender's attention, and ordered. Whilst waiting he looked back at Anita, jeez she was lovely, her hair flowed nicely down her shoulders. He was pleased to see she was trying to sort herself out, purse open and playing with makeup, and checking herself out in a compact mirror. So hopefully, she was feeling a little better about herself.

Anita thought she would stay and talk, Bob wasn't the first married man to engage with her. She could wait and see how long it would be before he tried to grope her in the corner or suggest a knee-trembler in the car park. It was her best option for entertainment at the moment.

Although he was nice and being sweet to her, with a genuine interest in her, her comment on liking stiff cocks hadn't changed his tack of conversation, nor had he turned into a creepy, groping maniac so she decided to stay on this pleasant channel surfed TV station.

Bob returned and placed the drinks down, closer together, so he could pull his stool closer to her. The sun was very low on the horizon and with the bar fairy lights on; they were sitting in a twilight glow.

Bob looked down at the veranda again, "Anita, forget the ex, there are plenty more fish in the sea, Miss Yellow Dress may look for a shoulder to cry on when she catches Mr. & Mr. ravaging each other later? What about the athletic blond just coming off the beach, the one carrying her dog? She looks a cracker."

"Oh Bob, it's not that easy, surely even when you were young it wasn't easy to pull, even as a catch like you?" replied Anita smiling.

"No you are right, my chat-up lines were always corny, I was never lucky- until I met my wife Sue." He replied "But surely there are clubs, chat rooms, singles dating apps that will get you in touch with other people looking for the same," said Bob, hoping he wasn't losing her by showing the generation gap.

"It's not as easy as that, as I am also carrying a bit of extra baggage," answered Anita, grasping his upper arm in a brief hug.

"Ok sorry, you don't have to tell me if you don't want to, we can keep things light," said Bob, trying not to lose such a nice engagement.

"What you need is a fresh start to like yourself, and someone will like you too, that is what Sue used to tell her friends," Bob said, trying to sound as sympathetic as possible.

Bob and Anita continued to get on famously as the evening wore on, their conversation covering a wide range of topics. She enjoyed being with a father figure that she never had, and he enjoyed her attention. They shared a common sense of humour despite the generation gap.

Anita giggled as she finished her gin, "Come on Bob, drink up I'll buy this time, so you won't feel insecure. Do you fancy some shots; I'll mix and match if you don't know what you like?"

She stood up; Bob nodded and finished his pint, turning so he could watch her walk away. A few steps down the bar she turned to catch him watching her, cheekily smiled, and wagged her finger at him, like a naughty boy, then continued once she saw him blush.

She had a lovely thin hourglass shape, her hip, and skirt swaying with each stride. Bob lamented his older age if only he was younger and she found him attractive.

She returned with a tray of 6 shot glasses, placed the tray between them, sat down and offered Bob one, as he took it she picked up one toasting Bob, "Here's to you Sponge Bob and the sun going down," grinned as she downed it in one.

Now darker with the bar just dimly lit by the cheap fairy lights they were in the shadows, the music had crept up louder, people were coming and going off to clubs.

Bob and Anita chatted on whilst Bob pointing out sexy ladies or what he thought may be hunky men as they passed, often with Anita making light comical appreciative, "Phworrr," noise, leaving them both chuckling.

During one thread of conversation, she accidentally called him daddy, which he found a little discerning, but Bob did secretly like it. He and Anita got on to hand-holding, arm hugging terms, gradually increasing with frequency, as they sipped their way through the shots, as they giggled at their sarcastic jokes, often at other people's expense.

"Now come on Anita, anyone of these clubbers would love a pretty, gorgeous thing like you to be their girlfriend, isn't your gay radar ringing at all this evening," said Bob showing up the generation gap.

"I wish it was as simple as that Bob," said Anita. "I wish I could explain".

"But you are stunning, your hair, your body, especially with those freckles," defended Bob grinning at her.

Anita couldn't believe her luck he was so genuinely honest, he actually was just talking to her for conversation. There was no groping or innuendo; he was open about his desire for his wife. It was sweet how he tried to cheer her up by playing cupid with her now being single. His patriarchal care and conversation made her feel the emptiness of that relationship she never had. Strangely, she wanted to share her secret with him, to gain his approval and paternal support.

Anita leaned closer and her one hand lightly took Bob's left hand and drew it down between her legs, under her skirt to her crotch, Bob felt her hand fiddle with her underwear and then a small limp warm cocktail sausage-like member dropped into his fingers. She looked at him, eyebrows raised, and she removed her hand.

Bob wasn't sure what she was doing, or what she expected him to do, but he knew what he was touching. He had never played with any other man's cock, let alone a beautiful woman with a limp cocktail sausage.

Not knowing what to do, curiosity took hold, and he started twiddling his fingers around the small flaccid dick that was now slowly waking up. Almost like he was checking it was what he thought it was.

Looking into her eyes, she was waiting for some kind of reply, but he didn't know what to say. Gently rolling her growing dick in his fingers, whilst still a little in shock, he took it in between his thumb and 2 fingers, whilst growing but still limp, sliding his fingers up and down along its growing length.

Anita's eyebrows dropped, and a smile broke out. She leaned in and pecked him on the cheek. Her warm limp short sausage continued to grow and fill with blood. Bob could soon roll his hand around it and just lightly squeeze it, as he continued to stroke it. Yes, it was what he thought it was, but unlike all his male programming, he enjoyed holding it, knowing that it was attached to this pretty, witty, gorgeous young woman.

"Ahem, Well I never expected that," said Bob as he now released his hold on her and withdrew his hand. "I can see how that constitutes extra baggage. Not that it is bad, but I think I understand your dilemma now. So for an old fart, what is the right term, you know? Are you a trans...Err...She?" Bob stuttered uncharacteristically, not want to cause insult. "I have noticed those aren't just socks stuffed down there," as he nodded to her breasts.

Anita smiled "Trans woman, or T-girl if you like. I was born a boy, growing up without parents around, just me and my sister I found I only understood and fitted in with girls. I shared the same interests; I fancied other boys, makeup, fashion, feeling more comfortable in her clothes and underwear, which she caught me wearing her best lingerie when young. Rather than her getting angry and ridiculing me, she supported me, helped me with sizing clothes, makeup, discussed other boys and favourite film stars, but also helped me to love my body.

"I got drugs to stop the testosterone and grow breasts. I live as a woman, but I just can't lose that last thing. I do just love both mine and other men's cocks. I saved some money along the way for some light surgery to help and tweak things to become what I wanted physically. But it seems I am still not confident enough to enjoy what I now want, a one to one committed relationship."

"Do you want to see me in all my glory" Anita continued, wanting to up the stakes, as she flicked with her phone and showed Bob the screen. The first photo was stunning; she was naked wearing full black suspenders, see-through Vee plunging knickers, black see-through low cut bra, no glasses, with a come hither look.

He flicked across a few more, some with penis tucked in or just poking out various panties, the last one with her led on her back, with Anita looking down through her breasts, between her legs high in the air; dick loosely flopped to one side and anus on full display.

Bob found himself turned on and his penis stiffening to rock hard as he flicked through her album of erotic photos but was surprised to realise Anita was stroking his hard-on through his shorts.

"You like what you see?" Anita quizzed, asking for validation of her own body.

"Do you need to ask? I think you are feeling the result, Those are stunning photos, thanks." Bob said as he handed back the phone, "So what are the plans for tomorrow? I'm free."

Anita smiled, gave the head of his dick one last soft squeeze, and withdrew her hand. "Well, part of my plan to be more confident is to do more outdoor stuff, so I had looked at surfing lessons; I've never swum in the sea, let alone surfed in it. I checked out the surf schools this afternoon, but was too nervous to book anything; the one I liked said they had availability from 11 am tomorrow. They do the suit hire, boards, and lessons all in."

Bob smiled and turned to her, "Right that is a date then, I can swing by your place at 9, we can both have breakfast then have surf lessons together. I've only body boarded but not full surfing, so you can't back out and I can be there for support. Come on Anita," Bob clapped his hands lightly in a mock football chant, "Anita surf those waves."

"Oh, that would be lovely," Squealed Anita in delight, wrapping her arms around Bob in a hug, kissing him on the cheek.

Anita was glad she had spent such a nice evening and now she wanted his desire and love, like all the others, just for a few hours, after all, he will soon go back to his wife and it wouldn't mean anything except some meaningless fun.

"Today has been emotional, so I am glad you were here to chat with me, it's been lovely spending time with my daddy and tomorrow would just be divine. I assume you are going to walk me home and then you'll know where to find me?"

"Obviously, I can't have a daughter of mine walking these streets at this time of night," he joked, as they rose off their barstools, he wrapped his arm around her waist and they walked on.

Anita's holiday apartment was on the other side of town to Bob's. Once there, Anita invited Bob in for a cup of tea or coffee, which he accepted, guessing it means the same today as it did when he was younger.

Bob wasn't sure why he had gone this far. He tried convincing himself that it was just for a cup of tea, but he knew if Anita put herself on a plate for him, he would take her. But he didn't know why, was it his desire for some forbidden fruit, or just an available vessel, or to help her, repair her loss in a protective embrace, or just a late midlife crisis. He just didn't know, except he did lust after her and wanted carnal knowledge of her body.