Suitcase Shambles

This is a story about a divorcee whose ex had crushed her confidence, and how her friend helped her in ways she'd never have expected.

The story covers some mild reluctance and exhibitionism, a casual sex encounter and a lesbian experience. Because of the mixed themes, I think erotic coupling is the best category.

While it is long, there are multiple encounters to keep you interested.

A special thanks to RF-Fast for helping to proofread and ensuring the story is in good shape.

Suitcase shambles

"We should just do it!" Kimberly encouraged me.

"I don't know Kim. You know I can't afford it."

"I'll pay."

"You know I don't want your money!"

"You told me many times you don't want charity. But this isn't charity. If anything, you'll be doing me a favour."

This would be good. Kim was a force of nature and we'd been talking about my boss sending me to a conference on Thursday. He'd suggested, as I couldn't fly back until Friday morning, that I take the Friday off and make a weekend of it. She jumped on that, suggesting she come along, and we'd have a mini break together.

It sounded nice, but after my divorce a year ago, I'd been living with my stepdaughter virtually hand to mouth. No spare money for anything but the necessities. My ex had to pay court ordered maintenance and child support, but he'd been a dick about it. At first, he'd not pay until I'd hunt him down and virtually beg him for the money. When I told Kimberly about it, she insisted I get my lawyers on it and after that, he'd hidden behind his lawyer, trying to delay and renegotiate. In the meantime, my earnings barely kept my head above water.

Kimberly had offered me money, even calling it a loan that I could pay back if and when I was able to. To her, the money was nothing following her last divorce. She'd been married 3 times and the last guy had been very wealthy. Add to that, he was handsome, charming, and charismatic. The only downside was it turned out he was gay and left her for another man. Weirdly, they were still friends, and she even got on with his new boyfriend. But I suppose a 7 digit pay out with the divorce eases the pain considerably.

After 3 marriages, she'd decided not to look for number 4 and was content to date younger men. A lot of younger men, from what she told me.

"How am I doing you a favour?"

"I've not had a holiday since my last divorce. Obviously, I can afford it, but I've no desire to go anywhere alone, and you know my rules about the men I date."

Because of her wealth, she felt she was a target for gold diggers. So, she made it clear to anyone she dated frequently that she was happy to pay for meals and such, but that was it. She'd not pay student loans, car payments or credit cards.

"So, why would you pay for me?"

"Because you always refuse any offers when I want to give you money. So, I know you're not trying to get into my panties before getting into my wallet." She said the last rather suggestively, and I had to laugh.

"I think you're safe on that account. What are you suggesting?"

"Your boss is already paying for you to stay overnight, so I'll rearrange your return flight until Sunday evening. Then I'll book us a room to share for Friday and Saturday nights. We can hang out and catch some rays by the pool. Visit the shops and do some window shopping. Maybe hang out at the hotel bar and see who tries to pick us up."

I shook my head at that, as she'd been pushing me to date again. When I pointed out I couldn't afford it, she just pointed at my bust and said that was all I needed to get free drinks. My step daughter might be ok with that sort of thing, but I'd always wanted to pay my way. Too easy to feel beholden and end up doing things I wasn't comfortable with.

To be fair, I had great boobs. 36D on my 5' 7" toned frame looked a little large, but not over the top. At 33, they haven't sagged, and I've kept myself in shape, meaning I look good naked. Not that anyone but me has seen me like that in several years. Unlike Kimberley, she'd gone out within days of her husband leaving and had a guy in her bed in no time.

Hardly surprising, she was gorgeous, even if she was a little elfin. Barely scraping 5' 0", very slight and slender with an enhanced bust, courtesy of her last ex, before he changed his mind on his sexuality. Her 'C' bust looked large on her, and she had no problem dressing to show them off.

To some extent, she and my step daughter shared that trait. My 18-year-old step daughter Madison had only moved with me when she turned 16 and became too much of a handful for her birth mother. I got the impression her mother's new boyfriend had shown a little too much interest in Madison. From how she dressed and acted, I could imagine it wasn't all one sided.

However, she and I got on surprisingly well. Potentially, because she was the near duplicate of me. The same height and build, except that she only had 'B' boobs. Something she was annoyed about, and I'd got Kimberly to talk her out of getting a boob job shortly after her 18th birthday.

I still remember the time when one of her boyfriends came up behind me in the kitchen and groped my bum whilst asking when I'd changed my hair colour. He was so embarrassed when he discovered it wasn't Madison. She was furious briefly when she found out, then nearly wet herself as she laughed at his cringing embarrassment.

"What about Madison? I'm not comfortable leaving her alone." Not that she couldn't look after herself, but the temptation to throw a party whilst I was away would be too much.

"I'm sure she'll happily spend a couple of nights with a friend. Especially if you bring her something nice back with you."

Kimberley was right. Madison jumped at the chance and offered several friends she could stay with. I chose Emily, as she was the most sensible of her friends and her parents were friends of mine.

On the Thursday morning of our trip. I struggled to get Madison moving at 6 am as we needed to drop her off at her friends and Kimberly was to drive us to the airport. She grumbled and groaned as I hurried her out to the car and put our suitcases in the back. I remember being surprised that her case was identical to mine. It was only a 5 minute drive to drop her off at her friends. And I was pleased to see both Emily's parents greet Madison at the door with her case in hand.

On the plane, despite the early hour, Kimberly had a glass of wine. She was already in a holiday mood whilst I had the full day at the conference before I could let my hair down. In truth, I was a little worried about the weekend with her. She was my best friend and incredibly supportive during the breakdown of my marriage and divorce.

But she had a forceful personality, and I was used to her getting her way. She'd made several jokes about getting me laid, and I couldn't use the excuse that I needed to get home for Madison. Like I'd done previously when we went out.

It was too early to check into the hotel, so we left our cases at reception. Kimberly said she was going to scout out the hotel and local shops, whilst I took the courtesy bus to the convention centre for my conference.

The conference was busy and long, and I missed out on lunch as I'd got a call from my boss about something from one of my more difficult clients. During the afternoon break, I called the office to check everything was ok and my boss thanked me for helping. Hinting that I should charge something nice to my room for my efforts. I was fairly sure my boss was sweet on me, but knew it was too soon and inappropriate to ask me out.

Back at the hotel, I found Kimberly had already checked in and had our bags sent to the room. Using the key card, I let myself into our room seeing the twin queen-size beds. She was sitting on the balcony with a bottle of chilled white wine open and a glass full in front of her. I slipped off my jacket and tossed it on the bed. Then picked up her glass and downed it in one.

"God! I needed that." I said.

"Looks like it." She replied and refilled her glass and a second for me. "Ready to let your hair down?"

"Something like that. But I missed lunch and my afternoon coffee."

I sat and took in the view. The sun was close to setting, and it was warm, with a slight breeze. High in the hotel, the traffic noise was very slight, and it was remarkably peaceful. The hotel was one of the few tall buildings in the area and I could see out into the arid countryside a few miles away.

Kimberly told me about the hotel facilities and nearby shopping areas as we finished our wine. She took a quick shower, and I headed into our room and unbuttoned my blouse and lifted my case onto my bed. I was about to open it when Kimberly stepped out of the bathroom with her wet hair in a towel, and another around her waist.

I was a little shocked, as we'd seen each other in our underwear a couple of times whilst clothes shopping. But we'd never seen more, and I stared at her fake boobs like I'd never seen them before.

"What?" she asked, adjusting the towel on her head. I blinked and looked away, a little embarrassed.

"Nothing." I replied.

"Good, aren't they?" She asked and cupped her breasts and gave them a squeeze. "They look real, don't they?"

I had to admit they did. If I didn't know, I could have thought they were natural, even if they were a little big for her frame.

"Here..." she said and took one of my hands and placed it on her breast.

I was so surprised that it took a moment before I tried to pull my hand away. But Kimberly held it in place. She may be small, but was surprisingly strong.

"It feels like the real thing, doesn't it? Helps when you can afford one of the country's leading plastic surgeons."

Trying to get over the fact I was touching another woman's breast for the first time. I gave it a little squeeze and agreed it felt like the real thing. Kimberly surprised me again, as she reached out and touched one of my breasts through my bra. She gave it a squeeze once, then repeated the move on her other breast with her other hand.

"Yep, when my ex talked me into it, I was hesitant. But now I love them."

"Shame he didn't get the enjoyment out of them himself. Changing teams like that."

"I don't know. He seemed to love them when I got them done. Loved it when I'd wrap them around his dick. Of course, if he hadn't changed teams, he'd have loved to have seen us do this."

She gave my boob another little squeeze, then tweaked my stiffening nipple.

"Oh!" I exclaimed, then laughed a little nervously as I pulled my hand off her breast.

"Yeah, what guys don't like the idea of a couple of hot chicks 'lezzing' out?"

I struggled to open my case and when I managed to, I flung the lid open. Then froze in horror. The first thing I saw was a vibrator.

"What's this? It looks like you're really planning to let your hair down." She snatched it up and brandished it.

"That's not mine."

"Yeah, right!" She replied sarcastically.

"I don't own one, and I've never used one, ever."

"Really? I didn't think there was a woman under 80 who hasn't at least used one once."

"This is Madison's case." I pulled out a yellow, clingy Lycra dress.

Low cut with a short skirt, the sort of thing that couldn't be worn with underwear. Whilst I'd seen her wearing it and she looked amazing, I didn't approve. But Madison shared her willingness to dress provocatively with Kimberly.

"I'd love to have seen her face when she found she had your clothes. A bit of a sea change from what she'd expected to wear." She took the dress from me and held it up against me.

"I couldn't wear that!" I objected.

"What you mean is you'd not want to. You and Maddie have the same build, except for your big boobs, and the material is certainly stretchy enough to cope. So, you could wear it."

"What am I going to do? I've only got the clothes I'm wearing?"

"As I see it, the options are..." She held up one thumb. "First, you could cut short our brief break. Which would be a disappointment to both of us." She held up a finger. "Or you could try to make the clothes you're wearing last all the way through Sunday. Which is going to be tricky and limit what we can get up to."

She put the dress to one side and added another finger. "Or you could try to squeeze into some of Maddie's clothes."

She had a point. I spotted a cheesecloth peasant blouse, which I knew was big and baggy. I also saw a denim mini skirt that was shorter than I'd normally wear, but it wasn't indecent. A grin spread over Kimberly's face, and she held up a third finger.

"Or you could just go nude."

I laughed at the absurdity. "I'm sure you could hang out in the room and even sunbathe on the balcony in the nude. In fact, I might join you. I'm sure the hotel staff wouldn't mind delivering room service to the room of two hot naked women."

"I don't think so. Any other options?" I asked, and she held up her last finger.

"You could let me buy you some stuff. Even if it's just enough to get you through the weekend."

I sighed. Under normal circumstances. I'd have said no automatically.

"We'll see. I can wear what I've got on for tonight, at least."

After my shower, I walked out of the bathroom in just my underwear. After seeing Kimberly topless, it seemed reasonable. I found she'd spread out the contents of Madison's case on my bed. We might not be blood relations, but we shared our passion for an excessive amount of shoes.

There were skinny, cropped t-shirts and short shorts, but a set of lingerie caught my eye. Whilst most of the underwear was tiny, these were quality and expensive looking. Full cover, but sheer and lacy.

"I wonder where she got those?" I asked Kimberly.

"And how she paid for them. I've got several sets like that and you're taking over 200 a set."

"Really?" My mind jumped to worry over how she'd got them. Instantly thinking about drugs or prostitution.

"They must have been a gift from a gentleman friend. I told you I've seen her a couple of times with men in their 40s."

I'd asked Madison about that, and she reassured me she liked older men sometimes, and it wasn't a sugar daddy arrangement. Which didn't help my worries much.

"I'm slightly more confused about why she'd packed a vibrator. Between Emily, her two brothers and her parents, she'd not have much privacy to use it."

"Perhaps Emily and Maddie are closer than you think?" Kimberly said, and I blinked, not understanding.

Then I realised what she'd said, and my mind baulked at it. Not that I had any issues with same-sex relationships, but I just knew my stepdaughter loved sex with men. The idea she'd do things with another girl was just too big a thing to accept.

"Still, you'd think she could last a few days without it."

"Not everyone has such a low sex drive as you."

"I've not..., never mind." I started, but stopped myself. She had a point, I had to admit.

We went to eat and ended up in the bar, but just after 9 pm, I yawned and told Kimberly I was off to bed. The early start had caught up with me.

"I'm going to stay a little longer. See what the pickings are. You never know, I might be able to find somebody worthy of sharing my bed tonight."

"Really?" I was never sure when Kimberly was joking or not. "You'd bring someone back to our room?"

"You have three options if I do." She held up her thumb. "Stick your headphones in and keep your eyes shut." She added a finger. "Or you could watch and learn from an expert." Another finger. "Or you just join us. I'd not mind." She laughed, and I heard the alcohol in her voice.

She was a little louder than usual, then her eyes lit up. "Or I could find two guys. That way, you could have one after I'd finished with him. Or perhaps both." I blushed as I saw the barman had overheard and was grinning at us.

Back in our room, I changed for bed. Normally I'd sleep naked, but sharing a room meant I felt I needed to wear something. Slipping into a pair of my stepdaughters' panties felt weirdly exciting. A sort of taboo, I thought, and I was surprised to find the skimpy underwear oddly comfortable. With my philandering sociopath of an ex-husband, my choice of underwear had become simply utilitarian and cheap.

It was more of a struggle to pull on one of her t-shirts as it was skin tight and barely reached down to the bottom of my ribs. When I looked at myself in the bathroom mirror. I had to grin and hope this wasn't one of Madison's favourite shirts, as I'd definitely leave 'bump' stretched into the cotton.

Actually, looking at myself like that, I realised both Madison and Kimberly had a point. At only 33, I was too young to give up on finding a decent man. And in skimpy underwear with my tits stretching out the t-shirt, showing both my nipples and areola clearly, I doubt if I'd have any trouble finding one. At least if they saw me like this and not my usual frumpy attire.

I sighed and turned off the bathroom light and crawled into bed. I'd have to talk to Madison when I got home to double check if she'd be ok with me dating. And then I'd make sure she and Kimberly signed off on any guy I dated. My own judgement had failed me last time, so I'd let them vet the guys I'd date.

About 30 minutes later, Kimberly walked into the room to find me sitting up in bed reading my kindle Paperwhite. She entered the bathroom and left the door open so we could talk.

"No luck then?" I asked.

"No, too many middle-aged men who were probably at your conference. Most were not even trying to hide that they were married when they tried to hit on me." I heard her peeing and then the flush.

"Better luck next time." I commiserate with her.

"Hopefully, but in truth, I was hoping for something. It's been a couple of weeks since I had one of my special friends over."

"Weeks. Try the best part of two years." I replied.

The bathroom light went off, and she walked out of the bathroom naked, with her clothes in her arms. She turned on the small light at the desk and sat.

"And we all know you could change that fact like that..." She snapped her fingers at me.

"I know, and I promise when we get home, I will do something about it."

"Really?" She turned to face me.

"Yeah, I think it's time. But I'll need a wing-man or is it a wing-woman? It's been a long time since I dated."

"Don't worry, I'll look out for you."

She applied moisturiser to her face and neck, and I stared at her nude body. I can see her buttocks and back, and her chest in the mirror as she rubs in the cream. Suddenly I got a memory of the time she told me about her college days. She and a friend had let half a dozen guys wank off over their tits. It sent a shiver down my spine. Not that I'd ever tried that, but seeing her spread the cream over her face made me wonder what it would have been like.

"Tomorrow, I think we should hit the pool early."

"You think it will be busy?" I asked.

"Not really, but it got really too hot by noon to enjoy it comfortably, so we can come up here and clean up, maybe have a siesta. Then we can hit the shops. There is a nice mall within walking distance with a great AC."

A few minutes later, she crawled into bed.

"Does the light from the kindle bother you?" I asked.

"No. It's not that. It's..." I waited for her to go on and I was about to ask what the matter was when she continued. "I wasn't joking about hoping for some action tonight. Do you think Maddie would mind if I borrowed her vibrator?"

"Seriously?" I asked, half shocked and half amused.

"Is it too much?"

"Hell, it's your holiday as much as mine."

"Where is it?"

"I popped it in the desk drawer. Didn't want the cleaners to find it."

She jumped from bed and opened the drawer, then giggled.

"What?" I asked.

"It's just you popped it in the drawer next to the Gideon bible. One gives salvation and the other pleasure. I think I know which I want tonight." She turned and looked at me. "Would you prefer I did it in the bathroom? The bed would be more comfortable..."