Bob, Sue And Anita’s Holiday Romance - 1 free porn video

Bob sat on a stool by a shallow table window cill, high up, to one side of the `L’ shaped inside bar. He was tucked just around the corner of the short side of the `L’, looking through a hatch like window, which was dropped away and would be raised again after closing time.

Bob had chosen this cheap beach side pop up bar as it gave a great view across the beach and this stool position gave him a clear view across to the groups of millennials partying on the veranda below, so whilst out of the noise, hustle and bustle he could still crowd watch whilst also quietly sip a beer, check emails, texts and Face book on his old smart phone.

Bob was enjoying crowd watching, 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, 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 to squeeze into the even more isolated spot in the corner, against the wall on his left, at the end of the short leg of the `L’.

Bob looked round to smile, she was a nice thin build, wore a nice close fitting black Tee 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 really look up at the scene, just looked down and scrolled through her phone screen.

She appeared to be in her early twenties, her pert breasts trying to burst their way out of her tight Tee shirt, they weren’t overly large but nice.

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 really pert pair of buttocks and lovely athletic legs.

After a short while, Bob heard a stifled sob to his left, he glanced and noticed it was the woman sat in the corner. At first he chose to ignore it, as she obviously didn’t want contact. But by the third stifled bubble sob, he thought he should, she was obviously upset.

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 sentence. Now older, greying to white, after thirty years of marriage there was no longer any pressure to perform, or even try to obtain results. Plus people don’t feel threatened by an older person; he felt he could get away with more now when older than when in his teenage years.

She now had her head on her hands, talking quietly to herself, in a quiet whisper that Bob couldn’t hear, her tone was obviously anger towards herself. He did catch 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.

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 over hanging fringe.

She wore glasses that were the type you expect teachers or scientists in makeup adverts to wear; all she needed was a white lab coat. They were propped up on a lovely button nose, with nose and cheeks speckled with freckles that confirmed she was a genuine red head.

Her fiery look changed and relaxed as soon as she caught sight of him, so Bob took that softening change in her 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 obviously mad about his best mate Mr. Liverpool shirt and not his girl friend?” Bob persevered.

She blurted out a stifled laugh, brushed her fringe back and looked down to the veranda, 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 lovely, a really pretty twenty-something.

“He’s down there on the right, girl in a yellow top seems to be with him, but he is touching his mate at every opportunity, obviously 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” he joked,” no that’s the ex”. Bob hoped to lighten the conversation.

“No honestly, she suffers migraines something terrible, she will now suffer for two to 3 days. So I am kicking my heels for a few days.” He paused.

“So, do you want to talk about the bad news?” Bob pressed.

Anita looked back at Bob and smiled “As it’s you and you may be able to do me a deal on a patio” her eyes sparkled.

Bob laughed; she blushed and went on to explain...

“My latest failure of a long line of failures, I thought this was it after several months and I actually 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, I kicked her out of the holiday flat yesterday. That was a text basically dumping me and assassinating me with all my traits and bad habits.”

“She?” blurted Bob, 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 one actually sat next to him having a conversation.

“Well I am Bi-sexual, I love both and a few in-between” she smiled then whispered “but I do love a good stiff cock” giving Bob a wry smile.

Now it was Bob’s turn to blush. But it did stir his own dick, with just the thought of it.

“Ha ha ha, I am getting better at this” she blurted & smiled, leaving Bob with a quizzical look.

Bob had nearly finished his drink, draining it he said “would you like 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, managed to get the bartenders 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 feeling a little better about herself.

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 even with the bar fairy lights on they were 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 be looking for a shoulder to cry on when she catches Mr. & Mr. ravaging each other later?

Or what about her, just coming off the beach, carrying her dog, the athletic blond, with her camel toe crotch showing through her gym joggers? 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.

“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 little 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, 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, she liked being with a father figure that she never had and he enjoyed her attention.

They shared a common sense of humour despite their 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 on once she saw him blush.

She had a lovely thin hour glass 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.

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 own sarcastic jokes, often at other people’s expense.

”Now come on Anita, any one of these clubbers would love a pretty, gorgeous thing like you to be their girl friend, 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 leant 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 was 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 after a short pause, 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, 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, whist 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 leant in and pecked him on the cheek.

The warm limp short sausage continued to grow and filled with blood, he was soon able to 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 liked holding it knowing 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.”

Bob went on, “So for an old fart, what is the right term, you know? Are you gay, lesbian, transgender or cross dresser, I have noticed those aren’t just socks stuffed down there” as he nodded to her breasts.

Anita smiled “shemale is one but I like sissy boy, as it sums me up. I was born a boy, growing up without parents around, just me and my sister I found I only fitted in with girls. I loved their interests; I fancied other boys, the feel of 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 but also helped me to love my body. I managed to get some drugs to stop the testosterone and grow breasts, but I just can’t lose that last thing.

I do just love both mine and other men’s cocks. I have managed to save some money along the way for some light surgery to help and tweak things to become what I wanted physically, but mentally it seems I am still not confident enough to really enjoy what I now want now, a one to one committed relationship.”

“Do you want to see me in all my glory” Anita continued, 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 own 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 results, 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.

I checked out the surf schools this afternoon, but was too nervous to book anything; the one I liked said they had availability from 11am 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.

”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 stools, he wrapped his arm around her waist and they walked on.

Anita’s holiday apartment was 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.

Anita let him in and showed him around the nice holiday apartment, with one bedroom reasonably sized with bathroom and kitchenette in the lounge, where she left him and disappeared.

Bob filled & turned on the kettle, busying himself finding cups, milk and tea bags.

“So what do you think?” Bob heard Anita’s voice from the doorway, he looked up and gasped. She had changed.

Stood there provocatively framed in the doorway, glasses gone, in black lace stockings that accentuated her leg length as they sat high up, almost to her crotch, with self-holding tops, hip high black see-through knickers that dove down in a vee to her penis, which was only just tucked in what little material there was at the base of the vee.

She wore a black see-through bra, which gave her quite a cleavage, revealing nice pert nipples through the pattern.

“Ahem” Bob cleared his throat, as his penis throbbed into life, then to give him time to take it all in “give us a twirl baby doll” (a term he would never use with his wife Sue).

She stepped into the lounge, raised her arms up above her head clasping her hands together, revealing her shaved armpits, in fact excluding her hair, there was not a single hair on the rest of her body as she slowly rotated, exaggerating her hip as her weight shifted from one foot to the other, that Bob could now see were in 4” high shiny black heeled shoes.

Her knickers were open at the rear, with two straps coming from each hip at the waist, down, round each cheek, cupping them, to then disappear in between her legs to her crotch, showing off her beautifully exposed rounded rear.

Bob let out a low whistle, as he admired her lovely round peach bum, her hair was flatly draped across her shoulders flowing down and cut into an arrow, pointing down the small of her back to the split in between her cheeks; the purple highlights mirrored that shape.

She looked over her shoulders “Daddy likes?”

“Daddy sure does” Answered Bob, trying not to drool; his penis was bursting at his shorts zip.

Anita smiled and rotated to face him and stepped across the room to him, as if she were on a fashion cat walk. Her arms dropped and her hands reached out to undo his belt, waist button then zip, pulling his shorts as wide as possible, reached in, she held his penis loosely with one hand and pushed his boxers and shorts down enough to release his throbbing member from its confines.

“Daddy has been so good to his sugar baby doll, she wants to reward him” she whispered as her lips touched his and softly kissed him. Her hand softly stroked his dick, once released from the kiss; she dropped downwards until Bob could feel her breath on his now stiffened throbbing member.

Her hand held his shaft hard at the base between thumb and forefinger. He felt her lips cool and damp as they landed on the skin at the end his stiff shaft, wrapping her mouth around his spade end, gradually sinking her mouth down his shaft, he could feel her tongue warmly licking him inside her mouth.

Bob gasped, not having had a blow job since long before Sue, this was unbelievable.

She sucked, lapping and lubricating his dick with her warm spittle, running her mouth up and down it, in time with her thumb and forefinger masturbating him.

He looked down to see her head bobbing up and down, on his now wet stiff rod; he laid his hands on her head, enjoying it. She sped up with her free hand lightly stroking his balls.

“I can feel I’m going to cum Anita if you continue but I don’t want to waste it. After all that drink I’ll barely make one shot, I need more of you” stated Bob, knowing that this late, as tipsy drunk as he was, if he came, it would be game over and there was more for them both to enjoy, he didn’t want just a late night blow job or hand shandy, he wanted to be inside her, to ride her, for her to enjoy him and his manhood.

She pulled clear, stood up fully, now slightly higher on her heels and wrapped her hand around his dick hard. “Come with me big boy” as she led him out, through the hall, to the bedroom using his dick as a lead, holding on tight, walking that cat walk...

Bob could have come then, but was trying hard to think of anything to quell the steaming volcano in his balls...

The bedroom was tidier than when she first showed it to him, she sat on the bed, picked up a condom that was already there, opened it, hung it on the skin clad tip of his erect pole and using her mouth unrolled it on his stiff shaft.

Bob thought he could die now and be happy; this was beyond his kinkiest dreams.

Anita picked up a bottle and poured some gel from it onto the stiffly erect fully filled condom “as it is your first time, don’t be afraid to use lots of lube, first use your fingers lubed up to loosen me up”.

She rolled over, face down, beautiful buttocks up in the air, legs straight but spread apart. Her feet still in her high heeled shoes planted wide apart on the floor, pulling her cheeks apart with her hands to expose her ring that was now calling to Bob.

Bob, took the bottle, poured some gel into her cheek crevice and with his fingers guided it to her tight start ring below.

“Mmmm nice,” she said as she wiggled her bum in invitation.

Bob gently circled his finger around her ring, keeping the gel lubricating, slowly he dipped his one finger in, dribbling some more lube in the little crater as he rotated it.

“It’s ok; go deeper, nicely done, go to the knuckle...” Anita almost begged.

Bob probed his finger deeper, starting to cycle it slowly in and out, taking Anita’s gasps and humming as approval. He then pressed a second towards the rim, Anita’s crater’s muscle star twitched and relaxed, allowing him to enter a second finger without too much effort and copied the rotation and pumping.

“Mmmmmm that’s nice, so nice, now try it with your magic wand, daddy I want your magic wand inside me”

Bob pulled his fingers slowly out, dropped some more lube on his condom and laid his cock’s head at her target star’s opening that was calling him to enter. As he saw her muscle star relax he pushed, but no luck, so he used some support from his hand, guiding and pushing slightly down into her with his finger, until his head squeeze to slowly enter, then to disappear suddenly as it popped in.

Anita gasped “Ahhh, fill me daddy, deeper in Daddy, your baby doll needs you”.

Bob slowly pushed deeper in, boy this was tight, wrapped around him like a tight glove several sizes too small. Anita also pushed back, still gasping.

Bob tried to be as gentle as possible, not knowing whether he was doing right or wrong, for him it was excitingly erotic, like he was eating forbidden fruit, he now knew why people raved about anal sex; her arse was a massive turn on, just so peachy beneath him as he watched himself sliding in and out. Her underwear just added to the delicacy, it was getting easier and he was getting into his stride.

Certainly the gentle writhing of her beneath him made him think she was enjoying it as much as he was.

“Oh, it’s been so long since I’ve had a nice stiff cock inside me” Anita said “it’s so much better than a cold strapon”. Hoping he could last and maybe manage a second shot, disappointed that she missed having his cum shoot in her mouth.

“I’m glad you are enjoying it, this is unbelievable” answered Bob “but I want to see you enjoy it, can we do it with you on your back, so we’re face to face?”

“Ohhhh yeessss” Anita gasped “that is so much better, I want to see you enjoy me, the same way you please me”.

Bob pulled out slowly and once free, realised how snug he was inside her, immediately wanting to dive back in.

Anita rolled over with a huge grin on her face, raised her stocking-clad legs up above her and with an arm under each knee pulled them back, so her feet, with her heels, were either side of her head, exposing her star clad cave as an inviting target for him to enter again, looking up she asked for more lube.

Bob was transfixed, she was stunning, and her black high heels were a real turn on with the black underwear.

Although he was unaccustomed to seeing another half-inflated flaccid member beneath him laid on her belly to one side, he found it also a massive erotic turn on as it was attached to Anita.

He poured some more lube on both him and her star winking cavity, but also onto her half flaccid warm sausage, leant in close engaging the tip of his stiff rod to her relaxing cavity and pushed. This time he just popped straight in, Anita gasped and kept her mouth open, her eyes on him in approval.

As he continued to slide in deeper she nodded in approval, her mouth open gasping.

Bob slid in and out, initially slow and long, then increasing his tempo “oh, oh, oh, please, harder” Anita pleaded with her eyes locked on him, nodding in approval.

Bob was still stood on the floor, leaning into her cheeks with his thrusts, “oh, yes, oh, yeah, do me, fuck me.” Anita continued.

Bob leant on her upturned thigh with one hand and the other softly held her lubed limp warm sausage between his thumb and forefinger and repeated to stroke her, gently rolling it “oooh yes daddy” Anita approved.

As she throbbed into stiffer life, slowly reaching for the sky, Bob found that exciting this beautiful young woman’s cock a massive erotic turn on. He increased both his hold on it and the length of his stroke of his hand along its short’ish 4 inch length. He stroked her in time with pulsating his own dick into her Anita was now grunting rhythmically with each thrust “umph, umph, umph”, mouth open, eyes begging him to drive deeper and harder.

Bob could feel that sensation in his own balls and stiff rod that he was right on the edge of coming, he raised the tempo again now bouncing off her arse with a resounding slap. He sped up his wanking of Anita to double time on her now fully erect member in his tight grip. After years of practice bob knew that this would feel great for her.

Anita’s eyes were almost rolling round the back of her head in ecstasy, mouth open “yeah, yeah, yeah, fuck me daddy.”

Then just as Bob thought that was his limit, he felt her love tunnel muscles grip him tighter, Anita squealed “Fuuuuuuuuck Yeeeeeeesss” as a huge narrow rope of cum spurt from Anita’s own tip and she gave a yelp of pleasure “wooooooohh”, as another huge rope of cum looped in the air.

This was too much for Bob, feeling that familiar pressure surging from his balls, seeing her orgasmic delight and her released cum all on her was too much, he released his own volcano into his condom, driving his member deep into her and feeling its release, holding it into Anita as she continued squealing in pleasure “yeeeeahhhhhhhhhaaa”.

Bob pressed his shaft into her as long as possible, then as his spent rod deflated he, with his thumb and forefinger squeezed the last drip of cum out of Anita then released his hold on her deflating rod. He held the base end of his condom and withdrew, ecstatic that he had given Anita such a climactic orgasm, looking down at her beaming grinning face, with her belly and bra spattered with her own cum.

Just as he was about to just peel the condom off, Anita’s sat up, her hands came over and slipped it off for him, not losing a drop, inverted it and squeezed his cum out, running her fingers from the teat to open-end pouring it into her open mouth, licking her lips grinning.

Bob was aghast but also massively turned on, leant forward and French kissed her, tasting his own cum whilst at the same time disgusted with himself, not believing he was actually enjoying this, as it went against every red-blooded male cell in his body.

Anita wrapped her free legs behind him and pulled him over onto her, causing them to fall onto the bed, the pair of them kissing and laughing.

They hugged, both all sticky and sweaty, Bob exhausted drifted off to sleep whilst still stroking the small of Anita’s back.

Bob woke later, in the dark, now with a duvet thrown over them both and Anita wrapped around him, he checked his watch – Fuck 3am.

He jumped up, waking up Anita, “sorry Anita love I have to go, there is only so much I can explain to the wife”, he grabbed his gear, returned to kiss her and promise to see her in the morning and almost ran across town back to his apartment.

He managed to convince his wife he had met up with some lads on a stag do, that got him into a foam club party, so he could explain the later hour and the shower with his clothes on, washing away any cum stains.

To Be Continued *******

-->