Mandy had grown up in a small Midwestern city and was a shy girl. She had some close friends but had put aside the idea of dating in her early teens. Something about the complications of dating didn't appeal to her. It seemed like a lot of work for a few moments of pleasure. Besides, she told herself, too many of the guys she knew were pure unadulterated jerks. Those that weren't, she reasoned, would never go out with her.
For years and years she was able to put any thoughts of sex in the back of her mind and didn't worry about it much. Her self esteem was not great as she didn't feel attractive. Guys would ogle her body and even lick their lips. Mandy figured that they were laughing at her figure.
The reality was that Mandy was a larger and taller lady with attributes that lots of guys appreciated. True enough, if a guy liked a stick figure type than Mandy wasn't for them. But, if he wanted a curvaceous lady weighing about 190 pounds standing 5' 10" with perfect DD cup boobs then Mandy would be ideal.
Of course, Maggie thought her boobs sagged terribly and that no one would appreciate her size 16-18 body. Her lack of a positive self image might explain why at age 35 she was still a virgin. She hadn't even had a tampon or even a vibrator inside of her yet. She tried to bring herself off by masturbating but it never seemed as glorious as everyone seemed to imply it was.
Recently she was beginning to wonder about sex again. Maybe she should take the plunge, but how? She didn't want to date someone she knew as she didn't want her friends and acquaintances finding out she was a virgin and she worried about being 'sexually clumsy' around him. But, even more she was just too damn shy for the whole meeting and greeting and getting to know you scene.
So instead she bought herself a vibrator and hoped it would be some kind of substitute for the real thing. She rubbed it against her clitoris and it was pleasant enough. Her cunt muscles clinched and twitched but nothing mind blowing. She was hesitant to shove it up her pussy and therefore didn't.
Now thoughts of sex filled her waking hours. She went to internet sex sites and chatted with some nice people. But, she was not getting anywhere. If anything she was only getting more horny and more frustrated. This all explains why she was on her way to 124 Oak Street that morning a couple of months ago.
She was sitting alone at a restaurant sipping on a cup of coffee before work when she heard two ladies in the next booth talk about a male escort service. One of the ladies was telling the other how great it was since her husband had lost interest. Evidently the second lady had a similar problem as soon Mandy could hear the first gal giving out the escort service's phone number and a code word so that they knew that you wanted sex not just an escort. Luckily between the waiter saying the first lady's last name and the other lady repeating her first name Mandy had a name for a reference if she needed. Summoning up all of her courage that afternoon Mandy call 555-3825 and an answering machine picked up. Mandy almost hung up but gasping and then inhaling deeply she just gave her name and cell phone and said, "Secrets."
Pressing the off button on her cell phone Mandy was in a state of panic trying to catch her breath. What had she done? What kind of woman would use an escort service and have sex with some kind of gigolo? Obviously there must be a lot of women to use them or they wouldn't be in business she finally rationalized to herself.
Walking down Oak Street she couldn't believe how nice the neighborhood was. It was filled with high class homes and small shops. Then she saw the address above the door. This couldn't be right she thought as it was a children's bookstore. Reluctantly she walked inside and nervously asked the clerk if she knew where "Oak Street Secrets" was.
A kindly gentle smile came to the clerk as she asked if Mandy had an appointment and then showed her the stairs to the second level. Mandy was greeted by an 18 year old girl who told her to have a seat in the plush lobby and that Mrs. Robinson would be with her in a minute. Part of Mandy wanted to flee.
The door to the inner office opened and Mandy's jaw dropped as out walked a very demure 65 year old lady. Again, she wondered had she misunderstood what this business did. Sweetly Mrs. Robinson beckoned her to follow her inside of her office. In a grandmotherly tone the older lady spoke, "I hope I don't offend you if I get right to the point. I assume that you are here because you want sex with one of my boys."
"Ah, yes; I guess so," Mandy shyly replied startled by the blunt matter of fact way her hostess spoke. She hoped Mrs. Robinson didn't notice that she was trembling.
"No need to be nervous honey; don't worry just tell me what brings you here and what you have in mind and Miss Sarah will find you a guy that will give you an experience that you will never forget. You'll get wet every time you think back on it," Sarah Robinson proclaimed proudly. She smiled at the girl reassuringly.
As her hostess poured Mandy a cup of coffee the virgin began describing her life and finally quietly admitted she was still a virgin. Sarah reassured her that they dealt with a lot of virgins some ten years older than Mandy was. Sarah pulled out a checklist and went over what Sarah thought her sexual likes and dislikes were.
Sexual tastes were, of course, much harder to figure out from a virgin but Sarah had been doing this since Lyndon Johnson was President in her mid-20's. She almost always pegged a gal correctly. Then she asked Mandy what she wanted her stud to look like and what kind of personality type she preferred.
Nervously Mandy told the madam that she wanted a tall guy since she was tall herself. Of course, she wanted someone in great physical shape preferably a more mature guy 15-20 years older than her, but the most important thing was that he be a great talker as he would probably have to lead the conversation. The next thing Sarah did shocked Mandy as she didn't think of this possibility.
"Sweetie I need you to remove your clothes down to your bra and panties. I know one of my boys is perfect for you but I need to see your body type to get the exact right match. After all, you are spending a lot of money and I want you to be happy so you will come back again," Mrs. Robinson spoke softly.
Maybe this was a mistake Mandy thought as she stood up to leave. Inhaling deeply she was struck by the thought if she didn't do it now she would never lose her cherry. Almost panicking she stripped down for the madam. Sarah strolled over and looked up and down all of her client's body. She briefly touched Mandy's bra cup to see how much padding it had. Sarah thought it was too bad that Mandy wasn't there for a woman as she would service the lady herself.
Handing Mandy back her clothes Sarah returned to her desk and looked over some files. She then selected five thin folders out of her drawer. Laying the folders in front of the customer she calmly stated, several of my boys would love to get to know you. The top three are probably the best ones for you but it is your choice. Pick two and then we will see which one will be available first."
Mandy scanned the contents of the folders which had three pictures of each gentleman along with a description. One picture was a frontal view of the man fully dressed and the other were of the guys in tight bikini underwear with front and back poses. After a couple of minutes she looked up and with a raspy voice said, "I guess I like Rick and Tom the best."
