Giving in to Reg
Copyright© 2026 by SLUTWIFESARAH
Chapter 1
True Story Sex Story: Chapter 1 - Sarah, whilst away in Dubai with her husband attracts an older man, Reg. He comes on to her, encouraged by her husband. Sarah hates him, he's a pig, almost misogynistic and so full f himself, almost everything she despised. Yet Reg somehow wins her over and Sarah gives in, letting Reg take her with his massive cock. Then a rollercoaster of sexual, gratification and new horizons begins.
Caution: This True Story Sex Story contains strong sexual content, including Mult Coercion Drunk/Drugged Reluctant Lesbian True Story Sharing Slut Wife Wife Watching Interracial Black Male Black Female White Couple Anal Sex Cream Pie Double Penetration First Massage Oral Sex
Ted and Sarah Simmons were on a kind of a combined work and holiday trip in Dubai. Ted had a work assignment there, which he hadn’t really wanted to take as he had recently been away from home for an extended period. However the company involved really wanted him, as he was the Director of his company and therefore the top man, so to persuade him they had offered to fly him and his wife out, first class, and provide them with a private suite with an enclosed sun terrace. After looking at the task it was clear that it was really beneath him and as such he would probably only need a couple of hours each day for maybe half the week they would be out there so he agreed and of course Sarah was glad of some sunshine away from the cold UK winter and an excuse to shop tax free.
As Ted had suspected the job was a breeze and he was pretty much through with work by lunch for the first two days. Evenings they ate in the hotel and enjoyed drinks in the bar. It was clear that most of the patrons were older than the mid thirties couple and Sarah got more than one glance of the mature business men staying at the hotel, one in particular was called Reg. Reg was in his late fifties, and was a typical wheeler, dealer cockney, brash and bold, dripping in tacky gold jewellery and generally addressed all women as “sweetheart” much to Sarah’s dislike.
However, despite her obvious cold shoulder he always used to be on hers, or hers and Ted’s shoulders, metaphorically speaking. Everytime Sarah was at the bar or pool ordering a drink she generally heard the dulcet tones of reg saying, “that’s on me sweetheart.” Each time he met the couple Reg insisted on shaking Ted’s hand and kissing Sarah on the cheek, whilst surreptitiously letting his hands wander over her back and even buttocks. One evening after Sarah had retreated to their suite Ted and Reg had a few drinks. Sarah had asked Ted to deal with his behaviour.
Ted had full intentions of doing just that but a couple of things Reg said to him made him hold off. “You know Ted, your Sarah reminds me of my late wife. She is so beautiful, kind, funny and charming. You’re lucky to have her.” Reg said, as he ordered two more expensive malt scotches. As Ted thanked him Reg, now, like Ted, a little drunk said, “ere! If you ever get bored with her or need her, ya know! Looking after! I’d be happy to step into the breach for ya my old son!” Reg’s comments struck a nerve. Ted had often fantasised about Sarah having sex with another man. They had even imagined and talked about it during sex role playing a few different variations, although it had generally been someone famous apart from the one time when it was the creepy landlord they had when they were dating and renting a place. Ted recalled how they had both really gotten off about Sarah having to suck the old man’s cock when they couldn’t afford the rent and how she loved it as it was so huge.
“Thanks! I’ll bear that in mind Reg.” Ted responded as Reg ordered two more drinks. “Christ! I gotta take a leak!” Ted said realising he and Reg were probably in for a long session.
“Me too, now you mention it!” Reg blurted out as he slid off his stool a little worse for wear and followed Ted to the restroom. Both of them were feeling the effects of the alcohol and whilst standing peeing at adjacent urinals, reg was swaying so much he staggered backwards. That was when Ted caught a glimpse of Reg’s cock. He had a full hand wrapped around the shaft as he held it to pee and there were at least two inches poking out, plus a big mushroom shaped head. Images based on pure lust fired up in Ted’s head of Reg’s huge cock, smashing Sarah’s pussy. He thought quickly and decided to try and connect the two of them. As they sat back at the bar Ted decided to take the plunge and asked Reg if he would really fuck Sarah given a chance. Once Reg confirmed it Ted decided to roll the dice and confessed it was something he and Sarah had role played but something he really wanted, although Sarah had, on several occasions, drawn the line at fantasy only. Then Ted said, “You know Reg, if you had a bit of a personality change around Sarah, be nice, complementary and not so brash. “She would be a lot less hostile if you do. Who knows, with a bit of encouragement from me and a few drinks she might let you fuck her.” Ted said with a chuckle as they bid each other goodnight.
As Reg lay in bed Ted’s parting words kept him awake and his cock throbbing wondering if he had been serious. He’d certainly heard about couples who were into swinging, maybe they were and Ted was sounding him out. Either way he had nothing to lose and the thought of bedding a hot beauty like Sarah was enough to make any man play nice. He decided he would do just that, after all his success in business had mostly been down to his ability to charm people.
The following morning Ted was up and in the gym early. When he returned to his room he woke Sarah and she asked him how his evening had gone and if he had sorted Reg out. Ted assured he had, knowing he had to keep his fingers crossed on the outcome of last evening’s slightly drunken conversation. Sarah was about to ask him exactly what was said when there was a knock at the door. Ted opened the door to see a member of room service staff standing there. She had her hands on a room service trolley and in a happy tone said, “room service sir.” Ted looked surprised as he, as far as he knew, they hadn’t ordered breakfast but he stood aside and motioned her in. As she pushed the trolley into the room she said,” breakfast sir, compliments of Mr White in the penthouse.” Sarah and Ted looked at each other, slightly bemused as the lady left the trolley on the edge of the room and left whilst saying, “no need to sign sir. Mr White has taken care of everything.
Once the door was closed Ted and Sarah stood by the trolley, there were bagels, smoked salmon, fruit, coffee as well as flowers and an envelope with ‘Sarah’ written on it. Sarah opened the envelope and pulled out a sheet of hotel stationary. On it was written, [ Hi Ted and Sarah, well mainly Sarah. Ted explained how my behaviour has upset and annoyed you. Please be assured I will endeavour to do better. You are two wonderful people. Please accept breakfast on me. Hopefully we can make a fresh start. I am actually a nice guy and hopefully you will give me a chance. Regards Reg]. “Wow! Don’t know what you said baby but it certainly had an effect.” Sarah said to Ted, sounding shocked but also pleased.
“Seems so baby. So what do you think? Be nice to him or not?” Ted asked.
“Well! Let’s enjoy breakfast and see what he is like when I see him next. I’ll decide then OK baby?”
Totally your choice!” Ted responded as he started to pour out the coffee.
Ted returned from work a little after lunchtime and asked Sarah what she wanted for lunch. “I’ve eaten baby!” She quickly responded. As Ted looked at her with surprise she went on,” I bumped into Reg in the gym. He was totally charming. Anyway we were on adjacent workout bikes and chatted. He was charming and funny. He asked after you and I told him you might be back late, which was annoying as I would be starving after working out. So he suggested he treat me to lunch. Hope you don’t mind. I was famished.”
“Ted had to try hard to hide his delight as he simply asked, “oh! How was it?”
Sarah smiled and replied, “it was lovely. All the staff know him so well he gets very good treatment.”
“So! He’s off the hook for his previous transgressions is he? Ted asked.
As she answered, “I think so.” Ted felt a definite twitch in his cock.
Ted and Sarah decided to relax by the pool during the afternoon, Ted got a snack from the pool restaurant and as he sat and ate it he texted Reg. Just a simple thumbs up sign after letting Reg know that he and Sarah were by the pool. When he finished eating Ted joined his wife at the pool. After a few drinks, during which Ted kept his eyes peeled, scanning the area he saw Reg. Reg had clearly spotted them and was heading straight for them. As he approached Ted quickly told Sarah Reg was inbound and she sat up, just as Reg got to them. “Afternoon! It’s a nice one isn’t it?” Reg called out as he worked hard not to admire Sarah’s firm D cup tits, nestled in her bikini top. Just the thought of feeling them was making his massive cock throb.
Once the couple had greeted them Reg said, I’m glad I caught you. I’ve been let down by a golf buddy and tee times are hard to get. Shame to waste it.” Ted looked anxiously between Reg and Sarah and was about to say it wouldn’t really be fair on Sarah, given he had already left her for a day, when Reg said, “I mean both of you. I can easily swing a three ball instead of a pair. I wouldn’t want to leave Sarah out of it.”
Sarah chimed up, I’m up for it. Although I don’t play that often and I’m not that good compared to Ted.
“Well! I’m rubbish so you will be in good company.” Reg responded with a laugh.
An hour later the three of them were on the first tee, Reg having sorted two buggies, one for him and one for the couple. However, as the game unfolded it seemed Reg was as bad as Sarah, or he was deliberately hitting his ball that way so more often than not it was Reg and Sarah sharing a buggy, with Reg letting Sarah drive, whilst he admired her long, tanned athletic legs. Sarah was having such a good time she didn’t even react negatively when at the end of the round Reg patted one of her bare thighs as he said, “that was fun. You played really well. Far from being put out, Ted was delighted with how things seemed to be moving, although he still wasn’t sure how he was going to get Sarah to have sex with Reg.
Following the game of golf they returned to the hotel and Reg insisted that he buy the couple dinner for making his day so much fun. After agreeing Ted and Sarah went to shower and change, agreeing to meet in the bar at 8PM. After showering the couple lay on their bed in the cool room and Ted decided to probe Sarah’s mindset regarding Reg saying to her,” you seemed to get on pretty well with Reg today babe.”
Sarah replied, “yes. He’s pretty funny and actually quite sweet when you get to know him. Although he is a bit of a crafty old sod. He patted my thigh at the end of the round and I swear he was actually feeling it. I also caught him eyeing up my ass a couple of times.”
“Really? Want me to have another word?” Ted asked.
Nah! It’s ok. It was harmless. It didn’t bother me really. Does it bother you?” Sarah responded.
“No babe. You know I love it everytime another man thinks my wife is hot, which he clearly does and you really are by the way.” Ted replied as he leant over and started kissing Sarah.
As one of Ted’s hands cupped one of Sarah’s firm D cup tits she knew where things were headed and knew they didn’t have time as they would have to shower again. “Hey! Later babe. We don’t have time for this, we have to meet Reg.” She quickly said to her husband.
Ted knew she was right so he stopped and quickly said, “you’re right, as usual. What are you wearing tonight? Hope it’s something that will show off your sexy legs. Maybe Reg will cop another sneaky feel!”
“Oh. You want him to do you?” Sarah asked.
Ted paused and looked into his wife’s eyes before saying. “As I said babe. I think it’s hot when a man comes on to my wife. Maybe you should flirt with him. Now that would really turn me on for later!”
Sarah looked at Ted in silence for a moment before saying, “come on. Let’s get ready. As she dressed Sarah chose a spaghetti strap dress that came mid thigh. As she did she wondered if Ted was serious and also if his comment had influenced her choice. She also wondered if he had been serious about her flirting with Reg. Those thoughts were still in her mind as they entered the bar and were greeted by a smiling Reg who said,” Sarah, may I say you look particularly lovely this evening?”
Sarah smiled and replied, “you may and thank you Reg.”
Reg quickly said,” let’s sit. I took the liberty of ordering you the hotel’s signature cocktail, but I also ordered you a glass of bubbly in case you don’t like cocktails.”
Sarah smiled and said,” very considerate and kind of you Reg. Well I suppose I will have to drink both.” During the meal Reg seemed very attentive and Ted noticed that he would often touch Sarah’s elbow or shoulder. He also noticed that Sarah didn’t object. Far from it and on a couple of occasions she actually put her hand on Reg’s thigh when she laughed at one of his comments. At the end of the evening Sarah even initiated a goodnight hug with Reg and gave him a kiss on the cheek. Once back in their room Ted wasted no time in kissing Sarah and lifting her dress off, running his hands and mouth all over her firm body which ultimately led to them having passionate sex.
After their fucking Sarah asked Ted,” wow baby what got you so riled up. My little flirt with Reg?”
Yes babe. It was hot to see you do it, especially the kiss?” Ted replied.
“Really? Well I wonder how aroused you would have been if I told you he squeezed my ass when we hugged?”
“And you let him?” Ted asked.
“Well you wanted me to flirt. I didn’t want to disappoint my hubby! “ Sarah replied.
“I did. Maybe tomorrow you can tease him a bit more. The thought of that really gets me riled up.” Ted said suggestively. As he spoke Sarah could see her husband’s cock swelling and stiffening, despite the fact they had just had sex. She didn’t respond but thoughts lingered in her head as she kissed her husband goodnight and went to sleep. The following morning Ted didn’t need to go to work and he asked Sarah if she wanted to join him in the gym. She explained to him that her back and shoulders were feeling a little sore after the round of golf so she was just going to do some yoga stretches in the room. Down in the gym Ted bumped into Reg and explained that Sarah had a sore back.
“Oh! That’s a relief. Obviously it’s not good for her but I thought I might have offended her last night when I risked a little feel of her bottom after she was pretty touchy feely herself last night.” Reg said.
“Not at all. She was rampant last night! You should try to go a bit further.” Ted responded.
“Really. Like how much further?” Reg asked.
“Well if it was up to me all the way but she has never done that and not sure she would.” Ted replied.
Reg took a breath and said,” I have an idea! I have a private doctor friend who gives me a form of Viagra. Custom dose in liquid form I use. He also has a little special thing for ladies, like a super aphrodisiac, I have given it to a couple of women I bedded and it really got them going. It is totally legal and it doesn’t knock them out, just kind of lowers their inhibitions and makes them really horny, so they are fully aware of what they are doing. Maybe we could slip her a bit of that?”
Although Ted knew it was a little underhand he rationalised it with the fact that Sarah would still know what she was doing and he would be there to put a stop to things if it became unsafe or if she began to object to what was happening. After he agreed with Reg’s proposal the pair came up with a plan to get Sarah naked in Reg’s penthouse and also how and when to administer the potion to her. It all started later that day when room service arrived at their room door with a bottle of champagne on ice and two glasses. It had a card with it on which was written, [Hi Sarah, sorry to hear you’re feeling stiff and sore. Hope this helps you relax. Reg. ]
“Oh wow! That’s so sweet of him isn’t it?” Sarah said to Ted as he popped the cork on the bottle. Sarah re-read the card, not noticing that Ted poured clear liquid from a tiny vial into the glass of champagne that he passed to her. After several sips Sarah decided to call Reg and thank him personally.
“It’s my pleasure. I would also like it if you both joined me for dinner. I sometimes get a bit fed up with my own company and you and Ted are great fun. Please say you will.” Reg said to Sarah.
Ted had his back to Sarah and smiled when he heard her say, “That would be wonderful Reg. What time?”
After hanging up Sarah said to her husband, “Reg is so kind. He wants to treat us to dinner again babe. Eight o’clock in the bar. What shall I wear?” Ted felt his cock twitch as he walked over and stood beside Sarah as she looked into the wardrobe. Ted paused for a moment before pulling out a hanger with a low back black dress on it.
“Really?” Asked Sarah. I have to go braless with that dress baby?
Ted looked at her and responded. “Well go pantieless as well baby. It will be exciting to know you are naked under the dress when Reg admires you.”
To his surprise and joy Sarah just looked at him and replied, “Ok you naughty boy. You got it and I suppose flirting is required?”
Ted simply nodded and tapped his glass against Sarah’s before they both drained them.
As Reg caught sight of Ted and Sarah walking into the hotel bar his cock throbbed. It was all he could do to keep his jaw from dropping at the sight of Sarah. Instead his lips curled into a smile as his eyes focussed on her firm breasts swaying freely beneath the thin fabric of her dress. He admired her long tanned legs, legs he was planning to have wrapped around his waist that evening and when she arrived, giving him a hug and a kiss on the cheek his hand found the bare, warm and soft flesh of her exposed back. As they hugged he could do nothing to prevent his huge cock stiffening a little and press against Sarah’s leg. “Oh! Err, good evening Reg!” Sarah said clearly, feeling Reg’s cock against her.
The three of them sat as Reg said, “I ordered champagne for all of us.
“Ooooh lovely! Although at this rate I’ll be a bit squiffy before we have eaten.” Sarah said as she drank the cold fizzy liquid, totally unaware that it was laced with something intended to get her feeling different than just squiffy.
After drinks they dined and the meal was excellent. When the server asked about any after dinner drinks Reg suddenly said, “You know what Ted. I just got sent a fine bottle of scotch from my supplier to try. You have very good taste. I would value your opinion. We can go to my penthouse and sample it. I can get anything you want sent up to Sarah. How about it?
Before Ted had a chance to answer Sarah said, “oh wow. I’d love to see your penthouse Reg.”
Ten minutes later they were all in Reg’s penthouse drinking and chatting when Reg suddenly asked Sarah how her back and shoulders were. When she confirmed that they were a little stiff he offered up, “just as well for you I’m qualified in sports massage. Here let me have a feel.” Before Sarah could say anything Reg was standing behind her, his fingers firmly tracing along the top and back of her shoulders. At first she felt uncomfortable but then Reg pressed his fingers into her shoulders in such a way it seemed to bring instant relaxation and relief.
“Ohhhhhh! Mmmmm! That feels good Reg. “Sarah purred, as she rolled her head from side to side.
“Yeah. You’ve got a lot of pinched nerves in there, probably in your back. Head into the bedroom with Ted. Strip off and get on the bed. Take a couple of bath towels with you. One to lay on and one to cover your modesty. I’ll get my oil.” Reg said very matter of factly.
Before Sarah had a chance to answer Ted jumped up and said, “oh thanks Reg. That would be great. Head in babe and I’ll get some towels.”
When Ted joined Sarah in the bedroom she was already naked and sitting on the edge of the super king sized bed. She stood and Ted laid down one of the towels he had brought and before Sarah lay on it she looked at her husband and said, “are you ok with this baby? What if he tries something?”
Ted smiled and replied,”It’s fine. I’m right here with you. If he does try something will you let him? Go on! At least let him see you naked as a little treat for him!”
Sarah felt a little tingle of arousal go through her body and she wasn’t sure why. Reg! No way! She thought. But to her surprise she said nothing as she lay on the bed totally exposed. As Reg entered the room and caught sight of a naked Sarah and a smiling Ted, who was giving Reg a thumbs up sign he said, “oh lovely, you’re all ready for me. Ted could see that in preparation Reg had stripped off and just had a towel wrapped around his waist, a towel that was already tenting slightly due to the fact Reg was already getting hard.
Reg was carrying a tray with a metal bowl on it on a metal stand under which was a candle. As soon as he put it on the night stand the vapour of the heated oil hit her nostrils and sent a wave of relaxation through her body. She took a deep breath, let out a long sigh and relaxed as her body went limp. Reg lifted the oil tray and poured some oil onto a cupped palm before replacing it then slowly drizzled the oil onto Sarah’s back, between her shoulder blades. “Hhhmmmm!” Sarah moaned as the warm oil was slowly spread over her back. Reg then began massaging Sarah’s shoulders and back. The noises she was making made it pretty clear to both Ted and Reg that she was enjoying it. Sarah began to feel in a mild state of delirium as Reg’s expert hands eased and soothed her body. The combination of the alcohol, the smell of the oil, Reg’s touch and the potion she wasn’t aware she had drunk were making her feel almost euphoric. So much so she didn’t even flinch when Reg’s hands went beyond her lower back and began massaging her firm buttocks.
Ted’s heart was in his mouth when he saw Reg’s hands slide off Sarah’s buttocks and stroke the inside of her thighs. Then his cock throbbed when he noticed a deliberate opening of Sarah’s legs as she parted them just enough to give an unobstructed view of her pussy. Reg also noticed Sarah’s reaction and knew everything was going to plan. Reg dipped his fingers into the warm oil then gently slid them over Sarah’s soft pussy lips. There was a slight tensing of her body and a little gasp, barely audible, but her legs stayed open and she didn’t move even when Reg slid one of his oiled up fingers into the slit of her pussy lips.
Reg teased Sarah’s pussy for a couple of minutes and with there being no objection he slid his middle finger deep into her opening. “Uuuuuuuuhhhhh. Hmmmm! Ted baby. He’s touching me. He’s touching my pussy. Aren’t you going to stop him?” Sarah softly moaned, her voice quivering as she turned her head and looked at her husband, who was sat beside the bed.
Ted smiled and shook his head before saying. “It’s ok baby. Tell him to stop if you want him to and he will.”
Sarah closed her eyes and softly said, “I! I can’t baby. I don’t want him to. It feels really nice. I’m sorry!” As she buried her face in the soft bedding and mumbled “Ohhhhhh! God! Sooooooo nice. Mmmmmmmnnnn!”