Extra Shift

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This was way beyond what he had hoped for. Her pussy felt amazing wrapped around his cock and once again he was determined to enjoy every second. Benny reached up and took her nipples between his fingers and gently squeezed and pulled them sending more jolts down to her pussy. 'God, he's a good lover. He knows which of my buttons to push and what's more he doesn't seem to mind my small chest.'

As she continued to ride her pussy along his length Benny pulled himself up and took her right nipple into his mouth to suck hard on it, alternating gently biting it between his teeth. The jolts running from her nipples intensified until she had to hold still and at the top of her voice gave an anguished groan at the same time as her pussy grasped his cock tightly.

Benny had never felt a pussy quite like this and he thanked his lucky star to have been sat in Theresa's side of the dining area -- or more specifically overhearing her dilemma that gave him a way to engineer the current situation. If he never had sex with another woman again, today would live long in his memory. As he had already come, Benny was able to last a good long time while Theresa continued to ride him through another two of her orgasms before he eventually let his second lot of come soak her insides once more.

As with their previous coupling, Benny wanted a cuddle and the two lay in each other's arms. He cleared his throat and asked "Do you need to get back home tonight? Why don't you spend the night, I don't like to think of you on your own at this time of night."

She stoked his face affectionately and replied "No, the kids are at my Mum's and so it would be nice to spend the night. That way you have time to give me a potted history that brought you to this point." They spent the next half hour or so going through Benny's life to date which Theresa appreciated the way he didn't hold back at admitting his own short comings but by the same measure he didn't let them hold him back. All the while they were talking he never let go of her once, even when he was waving his hands to gesticulate, with another man that could have felt quite clingy and yet with Benny the nature of the touches made it seem like affection.

As the story wound up Theresa's hand brushed against his cock, and it inflated again from her attention. Once more she took it in her hand and began to massage it ever so gently. "Mmmmm, nice" she commented "Is there anything you wanted to do that we haven't yet?"

There was but he wasn't about to say it and so his reply was "I've loved every second plus I did say we would only do what you were comfortable with."

"That doesn't answer my question" came Theresa's immediate response "I can tell from your expression that you're holding back on something. Blurt it out."

Benny winced and said, "I don't think this is the time or place." He could tell from her expression that she wasn't taking that as answer and a few heartbeats of that stare made him say "There is something, but I don't want to spoil the mood. It feels nice just laying here with you in my arms and the feeling is way more than I had expectations of."

"I'm pleased to hear that. Genuinely pleased" was her initial response but she pressed on "Now spit it out."

Benny huffed and shrugged before he eventually added "I've always wanted to try anal but never had an enjoyable time and as it's painful for the woman I'd rather steer clear of it if it's all the same with you.

'It is indeed painful, or at least it was with my husband' was the thought rattling around Theresa's head. Nodding her head Theresa said "It can be painful, but I suspect that will be the last thing on your mind somehow. The question is do you have any lubricant?"

Benny shook his head saying, "No lubricant, only petroleum jelly that I sometimes need to apply to my eczema when it starts in certain environments."

Theresa smiled and said "That will do. I want to demonstrate just how much I appreciate your generosity."

Benny tried shaking his head as he said, "There is no need, you've showed that appreciation in many forms already."

Theresa pushed him and said, "Stop arguing and go get the jelly." Secretly he was excited at the prospect, and she thought 'His cock says he likes the idea.' Benny returned a minute of so later with the jar which she took, twisted the lid off and scooped up a generous portion before twisting and starting to apply to her anus. 'The trick is to relax' she had learnt, long ago. Her ex-husband had insisted on fucking her butt every now and again -- whether she wanted to or not. Here's Benny wanting to but trying to put me off. He's overflowing with brownie points right now.' With the application done she said, "Lie down on your back as you were before."

Benny showed his eagerness to comply, and she found it quite endearing, it was nice to find a man who cared more for her needs than his own. When Benny was in place she crouched over the head of his cock, reaching down she was able to steer the head until it engaged with her sphere. 'Relax, relax' she repeated in her head as she took the head in. She gave a brief gasp and held still, and Benny's face immediately showed concern which prompted her to say, "I'm okay really, it just takes a bit to get used to working the muscles in an opposite direction to what they usually do."

Benny reached up to support her hands which was another brownie point for him. Over the course of the next fifteen minutes Theresa worked his entire length into her sphincter and eventually settled into his lap. Benny couldn't help himself and said, "I'll say it again, what a truly amazing woman you are. That feels phenomenal."

Theresa smiled the broadest smile he had witnessed as she began to work her tight ring of muscles along his length, the speed of her progress getting quicker with each rise and fall. Benny had the presence of mind to reach his left hand to play with her right nipple while his right hand reached down for her clit which he massaged in tune with her rise along his cock. The lady held still at one point as her climax hit with much wriggling and leg twitching. After she had calmed down Theresa wriggled around so that she faced away from him, but this afforded her the opportunity to look over her shoulder so that she could study his expression.

The way she looked over her shoulder at him, a look of pure smouldering delight, did for him as he gripped her hips tight so that his cock was fully embedded inside her ass and he let go of his come, baptising her bowels with his come. Theresa was reluctant to let his cock go but eventually she did slide to one side and cuddled up against her lover. She twirled his chest hair in her fingers and looked up at his very satisfied expression, her natural reaction was to smile although she also said "Thank you. You've managed to banish some bad memories of anal sex. I hope it felt as good for you as it did me."

Benny tightened his hold on her shoulder, he was almost tempted to say that if he had his way, he would ensure she never had to endure anything unpleasant ever again, but he merely said "Yes, it was very special indeed and you were the one who did all the running and so if it was pleasant then you deserve the lion's share of the credit." Theresa quickly drifted off to sleep, the feeling of being held close by someone so caring was the catalyst.

Benny reached over to his phone, pulled up his banking app and transferred the same amount from his account to Theresa's. After the sacrifices she had just risked trying to please him he wanted to do something nice for her as well as her kids. He also drifted off to a contented sleep until he felt her wriggle slightly but then felt a shove against his chest rousing him. Once she saw him awake, she pointed her finger at his chest again and said, "I thought there was some mistake when I got another message from my bank confirming a second transfer to my account, especially as it was the same amount but then the message on the payment said 'something for you this time.' We agreed just the one payment."

Benny shrugged and replied "All I meant was that I wanted you to be able to buy something nice for you. Last night was far beyond what I could have wished for, and I'd like to have bought you a gift, but I don't know enough about you yet that the gift would demonstrate just how special you are. You're not mad at me, are you?"

Theresa pulled a frustrated face and replied, "A little bit" after a short pause she smiled and said, "But only a little."

Benny smirked back and wriggled down the bed and moved her around so that he was curled up between her legs. He said, "Maybe this will go to demonstrate just how special" and proceeded to demonstrate once again how much he enjoyed languishing her pussy with a suitable amount of reverence. They curled up in each other's arms and eventually Theresa woke up with sunlight showing through the curtains. At some point she had wriggled round, and she found Benny spooned behind her with his arm draped over her holding her close, the gesture made her smile to herself -- it spoke volumes while saying nothing -- and she hunkered down to enjoy the sensations while her lover gently breathed against her shoulder.

Benny did wake up slowly and when he sensed her move, he apologised "Sorry I didn't mean to pin you under my arm."

Theresa rolled over and tenderly ran her hand down his cheek as she said "Don't apologise. It felt nice to be spooned as the morning peeped through the curtains. As I said last night it's been sometime, and I liked it."

Benny's heart leaped at the words, 'I think I'm falling in love with her' were his exact thoughts. He should have been startled by the realisation but instead it gave him a warm glow deep in his chest.

Theresa reached her hands down and took hold of his cock once more and felt that he was once again fulling eric. "Mmmm, a girl could get used to this reaction, especially after last night." She wriggled around so that she was on her back, and she opened her legs as wide as the space would allow as she said, "Come stick that lovely cock where it belongs."

If Benny were the type to pinch himself, now would be one of those times and quickly scrambled up to kneel between her lovely shapely legs. He slipped inside her in one natural movement and started to thrust his hips in a slow and deliberate pace until Theresa corrected him "Nice as that was last night, I need something more urgent this morning. Now fuck me and make it good." Benny certainly wasn't the type to ignore a lady's needs and grasped her ankles to place them at his ears while his hands grasped her hips and he started to hammer away at her pussy at an alarming rate. Theresa really enjoyed the change of pace; she came easily soon after the pace change and she was quickly hurtling to another when she felt the tell-tale signs of Benny's thrusting being off. He held on to her hips one last time and did another of those bellows as he emptied his come inside her. For the second time in less than 12 hours he had managed to make her orgasm as he himself came deep inside her pussy.

The two enjoyed yet another cuddle until Theresa went and put her lips around his cock reinvigorating it once more. She scrambled on to her knees and looked over her shoulder at him as she said, "Get that jelly again, I need to feel that lovely cock in my back door once more." This time she allowed Benny to apply the jelly to her backdoor and his cock to see how thorough he would be and yes, he passed the test by using way more than was needed. If anything, today's anal adventure was over way before they would both have preferred but there was something mesmerising for Benny watching the way her butt cheeks rippled and shook with each thrust.

It was during their habitual post coital cuddle that Theresa asked "If you have no plans today, can we meet again later before my shift. It won't require any further cash though you've been generous enough already."

Benny smirked as he replied "If I gave you every penny I have, it still wouldn't come close to demonstrating how much your words are music to my ears. Yes, I'd love to spend longer getting to know what makes you tick however I have to insist that your kids need come first and you spend some time with them. I'm here all day and so we can either stay here or we can head off somewhere. You say what works for you."

Another slew brownie points. She replied, "I need to head back home to change my clothes, but I'll happily come back here, and we can just sit here shooting the breeze" her expression changed to one of mischief as she added "Or we could always think up some new fun games to play. I will head back home for when the kids get home from school although they know they'll be heading to my Mum's while I'm on my shift tonight. Maybe I can pull an extra shift again tonight" with which she winked at him.

"Mmmm, I like the way you think" was his reply. She got dressed and promised to be back within the hour. She would have been back sooner, but she wanted to get her hands on some anal lubricant for later on. The kids would be at school, but she called in on her mother to check they were alright. As it turned out they didn't head anywhere and ended up sitting and talking for a while but then inevitably ended up back in bed for more fun and games until she had to leave to attend to her kids.

The following day was a repeat with one exception. Theresa was walking along the path to his boat when she thought she could overhear a conversation. It was obviously Benny's voice, but it appeared one sided, so she guessed he was on the phone. "Yeah, I'm all good at this end my friend in fact I'd go as far as to say I'm better than good. I think I may have very well found the one buddy." A short pause followed by "Yeah, she's amazing and beautiful in equal measure and I think I've finally found the one. Who would have thought, dear old Benny falling in love?" The last sentence stopped her in her tracks as she weighed up its implications.

Was it her he was talking about, but then who else could it have been? She admonished herself for having the slightest doubts -- this is precisely what she wanted when he had fucked her the first time. Men like Benny rarely came along in a girl's life and here was a man who cared about her feeling's way beyond any man that she had met in the past. As she climbed the steps to the deck, she was still debating how to handle this latest step until Benny popped his head through the hatch and then scrambled up to help her aboard saying "That's perfect timing. I was just talking about you to an old friend of mine".

He took her in his arms and kissed her passionately before she replied, "All nice comments I hope."

Benny smirked as he added "All glowing terms." They didn't go anywhere again that day, instead they adjourned to the bedroom where Benny made slow passionate love to her until he paused half way through "I hope this doesn't freak you out, but I mentioned to my friend that I think I've fallen in love. I've never met another quite like you." It could possibly backfire on him, but he figured the best things are worth the risk.

Theresa's response was to tighten her thighs on his hips, pull his face down to hers and kiss him long and hard. When she eventually pulled up for air she smiled broadly and said "Glad to hear it, I too have fallen in love. You are such a considerate lover but how does this fit in with you moving around." She was afraid what his answer would be but before they went any further the elephant in the room needed to be addressed.

Benny remained still, still buried in her clutching pussy and stared into her deep green eyes and smiled "something tells me my travelling days are behind me. I've found what I'm looking for even if I wasn't looking for it at the time." That's when the tears started for both, and they just lay there wrapped in each other's arms with Benny's erect cock buried inside her.

The coming weeks found them both buying amazing amounts of lubricant as they cemented their relationship, and it was some months before his boat moved again and then only as far as the nearest boatyard where he could put it up for sale. He had found the destination he wasn't looking for.

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  • COMMENTS
10 Comments
Cal59Cal59about 1 year ago

This was fine the way it is in the category it’s in, thanks for your work

WriteTyperWriteTyperover 1 year agoAuthor

Very useful feedback for future use. Thank you.

AnonymousAnonymousover 1 year ago

I would have loved him to gift her the money as a huge tip, and then invite her out afterwards. Don't make the transaction part of the deal. She might still feel obligated at first, but love isn't about the money. Just my preference.

With regard to whether or not sex belongs in this category, it does absolutely!

Some falling action about him integrating into her family would be nice too.

Overall, I liked it. Thank you for sharing.

WriteTyperWriteTyperover 1 year agoAuthor

Thank you for the feedback although I'm not sure I agree with you Anon. Given that the site is called 'Literotica' I read the category 'Non-Erotic' as that being the area for non-sex stories but would be interested to hear others opinions.

oldtwitoldtwitover 1 year ago

That’s a nice safe enjoyable story maybe just to nice a couple

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