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.
