Bob, Sue and Anita's Romance Pt. 01

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

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?" Anita said from the doorway. Looking up, Bob gasped when he saw that she had changed.

She stood there provocatively framed in the doorway, her glasses were now gone, she wore 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 in a vee to her penis, which was only just tucked in what little material there was at the base of the vee. She also sported 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 above her head, clasping her hands together, revealing that excluding her hair, there was not a single hair on the rest of her body. She slowly rotated, exaggerating her hip as her weight shifted from one foot to the other, that Bob could now see were in 4 inch high shiny black heeled shoes. Her knickers were open at the rear, with two straps coming from each hip at the waist, down, around each cheek, cupping them, to disappear in between her legs to her crotch, showing off her beautifully exposed rounded rear.

Bob let out a low whistle. She looked over her shoulders "Daddy likes?"

"Daddy sure does," answered Bob, trying not to drool; his penis was bursting at his short's zip.

Anita smiled and rotated to face him and stepped across the room to him as if she were on a fashion catwalk. 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 felt her breath on his now stiffened, throbbing member.

Bob looked down and watched her put her hand on his shaft hard at the base. He felt her lips, cool and damp as they landed on the skin at the end of 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. He watched and felt her suck, lap, and lubricate his dick with her warm spittle, running her mouth up and down it, in time with her thumb and forefinger masturbating him.

He watched 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.

Feeling the familiar twinge in his balls and shaft, he needed to warn her. "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 want to have more of you," stated Bob, knowing that at this late hour, 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 both 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 catwalk.

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 shaft 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 flower-like star-shaped 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 starflower below.

"Mmmm nice," she said as she wiggled her bum as an invitation.

Bob gently circled his finger around her ring, dribbling some more lube in the little crater. Slowly, he dipped his one finger in.

"It's ok to go deeper, nice." 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 flower 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 withdrew his fingers slowly, dropped some more lube on his condom, and laid his cock's head at her 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, guiding and pushing slightly down into her with his finger, until his head squeezed, entering slowly, then to vanish as it popped in.

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

Bob slowly pushed in deeper. Boy, she 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 exotic, forbidden fruit. He now knew why people raved about anal sex; her peachy arse was a massive turn on 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.

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 strap-on." Hoping he could last and maybe manage a second shot, it disappointed her not having him cum in her mouth.

"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 squealed. "That is so much better, I want to see you fuck and enjoy 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, removed her bra to release her bouncing pert breasts, led on her back, raised her stocking-clad legs 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.

She transfixed Bob. 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 lying on her belly to one side, he also found it a massive erotic turn on, being attached to Anita.

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

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.

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 leaned on her upturned thigh with one hand and his other hand softly held her lubed limp warm sausage between his thumb and forefinger and began to stroke her, gently rolling it, "Oooh yes daddy," Anita approved.

It turned Bob on, as he excited this beautiful young woman's cock, causing it to throb into stiffer life, slowly reaching for the sky. He increased both his hold on it and the length of his stroke of his hand along its length. He stroked her in time with the plunges of his shaft into her. Anita was now grunting rhythmically with each thrust, "Umph, umph, umph." Her mouth open, and her eyes begging him to drive deeper and harder inside her.

Bob could feel that familiar sensation in his balls and shaft, indicating 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 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 around 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 shaft tip and she yelped in pleasure "Wooooooohh," as another huge rope of cum looped in the air. With his thumb and forefinger, he squeezed the last drop of cum out of Anita and released his hold on her deflating rod.

This was too much for Bob, feeling pressure surging from his balls, watching her breasts bounce, seeing her orgasmic delight proven by her released cum all on her stomach and breasts was too much, he released his own volcano into her, driving his member deep into her and feeling its release and it was his turn to vocalise his pleasure "Yeeeeahhhhhhhhhaaa."

Bob pressed his shaft into her as long as possible, then as his spent rod deflated, 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.

Just as he was about to 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, leaning forward and French kissed her, tasting his own cum whilst at the same time disgusted with himself, not believing he was enjoying this, as it went against every red-blooded male cell in his body. Now not bothering about his long-lost taboos, he lapped her cum up from her breasts and stomach.

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 3 am.

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 promised to see her in the morning. He almost ran across town back to his apartment. He later managed to convinced his wife he had met up with some young lads on a stag weekend, 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, if you like it enough?

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymous3 months ago

This encounter felt so similar to many of my own hunni. So many men whose sexual potential is squandered in the monotony of a marraige that has lost all spark finally getting round to trying things they wished they had long ago x you do write well I am glad I read it. It is much better than my own efforts can't wait to read more. NaughtyAmy xxx

ptscuriousptscuriousover 2 years ago

Meeting a Woman such as Anita and ending up in bed with her has been a dream of mine for many years, I realise that it will never happen, however reading your story helps to fuel my fantasy and I look forward to reading more chapters.

Well written.

Virginiais4LoversVirginiais4Loversabout 3 years ago

While I’m doing my best not to judge “Bob, Sue, and Anita’s Romance Pt. 1” against Vicky and Alex, I need to shake off my recency bias. The stellar writing of “Victoria’s Secrets” and “Victoria & Alex Pt. 1” have me yearning for that same level of storytelling that made those so wonderfully memorable for me, and a true joy to see a trans-lady and her love, and allow me to lose myself, if but for a little while, in their lives, and their love-making.

As for the story, above, this is certainly a perfect-world situation for both Anita and Bob. Not having any real knowledge of one another, their connection seems to be almost instantaneous, bordering on the contrived. Certainly and seemingly good for Anita, as a lot of these real-world chance meetings can go off the rails so quickly and put her in danger (so I’ve heard). She demonstrates a surprising amount of trust and faith in Bob, even given her “live-in-the-moment” persona. She’s rewarded, either by luck, chance, or grace, by someone who has never revealed or displayed any tendencies towards trans-women, that the reader is aware of.

I don’t want to necessarily “poo-poo” it, because, overall, it was a fair attempt at trying to make the connection between themselves, to the reader. Again, the level and intricacy given in the set-up of Vicky and Alex is coloring my judgement, here. Establishing a bit more chemistry between Bob and Anita would’ve helped me appreciate their connection more. I would finally add that I don’t really connect with the term “sausage” in referring to the penis...seems rather frat boyish/machismo language. Those tried and true words that make erotica so great would’ve been better utilized...just my humble opinion.

Knowing that this was one of your earlier efforts, and to be fair to you, Nelly, I’d say you did well with Anita and Bob. As I submit this, I’ll be giving Pt. 2 my attention, next. Like many who have commented, I look forward to seeing where Sue fits into the picture, and how you develop each of their characters....:)

As always, I appreciate the effort and time you give, to allow readers like me, the opportunity to enjoy erotica in its written form. There are some absolutely gorgeous trans-ladies that I follow on Instagram and Tumblr. Being able to experience their beauty through the eyes of someone telling their stories of passion, love, aspirations, and sexuality takes on a completely different level for me...one that I savor.

AnonymousAnonymousover 3 years ago
Loved it!

Definitely want more!!

AnonymousAnonymousover 3 years ago
Great start

Waiting for future chapters

Show More
Share this Story

Similar Stories

Is She Smiling at Me? Pt. 01 Picked up by a girl at a bar, I get more then I expected.in Transgender & Crossdressers
Lily An accident leads to a very pleasant surprise.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
Something Better Unexpected love is the best cure for a broken heart.in Transgender & Crossdressers
More Stories