Chapter 1

How It Started

Emily was a recent widow about 40, trim figure with still firm, handful-sized breasts, and medium length wavy dark blond hair. Having no job skills beyond the mothering of two now grown children, her financial situation wasn’t good. To supplement the small life insurance proceeds, she decided to develop her 4-bedroom home into a bed and breakfast. Located within walking distance of the business district, she promoted to business travelers, promising personal service and home style lodging at a reasonable price. This worked well and word-of-mouth soon brought a goodly number of one-time and repeat guests.

Brad was one of her earliest guests and spent Wednesday and Thursday nights every other week while visiting his company’s home office. He was married and in his mid-30s. With his regular presence, he and Emily soon became good friends and she looked forward to the companionship. As a shy person with only average beauty and bust size, she had dated very little and married her high school sweetheart. Her low self-confidence held her back from dating now, so this male attention was welcome but made her realize how much she missed even the vanilla sex she’d had in her marriage. She had fleeting thoughts about Brad, but he was married!

One Wednesday evening, Brad arrived with an announcement, “Tomorrow is the occasion of the first anniversary of your business. I want to treat the celebration so be dressed up for a nice dinner when I return.”

They walked to her favorite restaurant and Brad bought champagne on the way back. Never much of a drinker, Emily got pretty tipsy as she snuggled up with her host in front of the fire he laid in. It had been a favorite romantic thing to do with her late husband. Her lowered inhibitions let her reveal her reminiscence. “I loved to do this with my husband,” she murmured. Brad bent his head down and gave a long kiss. Her smoldering horniness and need for affection triggered a strong response. Brad skillfully built her arousal and took her to bed. Having an attractive naked man between her legs for the first time in too long was almost more than she could stand. After her climax, Brad held her as the tears flowed and then gave her even more loving. Two successive couplings had never happened in her marriage and she was amazed and thrilled. Brad reassured her that he only had sex with his wife so she was delighted to enjoy him bareback since her tubes were tied. From then on she especially looked forward to the visits of this sexy younger man.

Brad guided her sexual awakening, leading her into things she had never before experienced. He encouraged her learning from the internet. She worked with him to improve her appearance and poise. Finally, knowing that his widely spaced visits could not keep up with her emerging sexual desires, he proposed a solution. To help satisfy her growing sexual needs, as well as increase the revenue from her guests, he suggested that she offer “premium services” to regular visitors that she felt were attractive and trustworthy.

Condoms would be required and the time spent in their room would be limited. The regular room charge would be doubled. Though Emily’s body was worth far more, she could justify this amount compared to the rates of the hotels in the area. She should not hide the income since tax evasion was penalized far more harshly than charging for sex. Brad would be her business advisor in exchange for free pussy. Emily would tease him about those terms for a long time and was always happy to pay the “bill”.

After a couple of sexual dry spells between Brad’s visits, this option became more attractive to Emily. Finally, she selected a guest and made the scripted and rehearsed suggestion.

Frank was a guest who had enjoyed Emily’s lodging on a number of occasions. He was a decade older, divorced, and a gentleman. When he checked in again she decided to brave it out. “Frank, I’m now offering a special premium service that I call ‘Bedwarming’. At a selected time I will turn back your covers and get under them for one-half hour. I will be without clothes for maximum heat transfer and you may join in to check on progress in almost any way you wish.” She blushed as she reached the end of her pitch, very nervous as to how it would be taken.

Her client had a broad smile as he nodded, “I’d like that very much. How about nine tonight?”

Her heart skipped a beat as she blurted, “I’ll see you then!” and slipped away, leaving Frank to enjoy the unintended double entendre.

At nine sharp she was in his room. The older man watched intently as her robe was dropped to reveal the best body he had seen naked in quite a while. She displayed all her charms as she got under the covers and he slipped his robe off to join her. She saw the hairiest male body of her limited experience and his equipment looked formidable too.

He felt her shiver and gently said, “You can’t be cold so are you nervous?” She nodded. “You’ve not done this before have you?” Another nod. “I want you to know you are the most attractive and the best bargain of any woman I’ve paid for.”

Emily blurted out, “How many is that?”

“Truthfully, you are the first!” That made them both laugh.

Per her coaching she reached for his genitals and was not surprised to find them ready for intercourse. She was surprised to feel an uncircumcised penis. She so wanted to look at it but stroked gently. “I’d like you to touch me,” she suggested and his big hands explored her, building her arousal greater than her anxiety. When she was ready, she rolled on her back and Frank got the wordless invitation.

It was the biggest vagina-filler she’d encountered. Feeling how tight she was let Frank know to take his time. He’d handled this before and was soon snugly buried in her and moving slowly. He stayed deep and rubbed his pubic bone against her clit. “Oh, that feels VERY good,” she said between deep breaths. The quickness with which the waves of pleasure rolled through her body surprised her and pleased him. He let his own pleasure go and she felt the hot pulsing in her stretched sheath.

He stayed hard, like Brad had done but not her husband. She murmured, “More?” and he gave her a deep and skillful kiss. The second pleasure peak took longer and when they were done he remarked that she’d not kept good track of time. Emily noted that fifty minutes had elapsed but she’d not regretted a single one. Nor the omission of a condom. She must be more careful about both from now on.

In her own bed she had a lot to think about. There was the marveling that although the basic act was the same, the times with each man were quite different. Their shapes, actions, and even smell made them unique. Would this be true for other clients? Would they be as pleasurable as Frank and Brad?

Later that night she emailed Brad with the news. She had been both scared and excited that first time but quickly began to enjoy the new cocks between her legs. From then on it was more a problem of limiting her availability than finding opportunities. Brad’s visits were the frosting on the cake as he was the only one who could fuck her bareback so she could enjoy the benefits of male juice in her pussy.

After retiring, Frank moved to her city and asked her out to dinner. Surprised, but flattered, she accepted. During their mealtime conversation, Emily asked what prompted his call.