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."
"Very good, now to make the arrangements. First thing is payment; I have a special deal for virgins. I will guarantee you will lose your virginity with this deal. It is called 'Super Virgin Contract,' do you want to hear about it?"
"Sure, well, I guess," Mandy was flustered but determined.
"For one fee I will arrange that Rick or Tom meet with you and take your virginity under the guidelines we work out. But, if you fail to meet your escort he will track you down and not give up until he has deflowered you. This contract has a clause that states he can take your body by any means he deems necessary to accomplish your goal and you can't file charges against him or me," the madam sat back waiting for a response.
Pondering the situation Mandy thought about what she was doing. It was scary that by signing her name she would lose her virginity. Of course, that is why she came into the service in the first place. She took a deep breath and scrawled her name to the paper that would change her life. Then quietly she asked, "What's next?"
"Well honey you hand me the money and we arrange your date and before you know it you are a woman of the world," Sarah smiled at the soon to be ex-virgin. Mandy gave the madam her Email address and the times she was available for a date. Not being a socialite she had lots of open times. Sarah showed Mandy out and returned to her desk.
There was a strange spring in Mandy's step as she headed back to work. At the same time her stomach was in knots but her pussy was suddenly very wet. What had she done? She hoped she wouldn't live to regret this decision. She couldn't wait to get home to check her Email messages.
Rick walked into the escort service office to have his biweekly meeting with Sarah. Serious business was conducted at these meetings as Rick would advise Sarah if a client was being inappropriate or if they should see an escort with different tastes. Sometimes, she would refer a new client his way instead of calling or emailing him.
The receptionist let Rick into Sarah's office that day and she had already stripped down to bra and panties. This was Rick's favorite part of these meetings as generally he was required to service his boss. Walking right up to her he kissed her with raw passion. To Rick this wasn't work as he really liked, maybe even loved, Sarah and was also a nymphomaniac who really got off on making a woman cum.
He was 50 years old with black hair and blue eyes on his 195 pound six foot tall muscular frame. Sarah almost liked being serviced by her boys more than collecting her fees and percentages. Rick's hands mauled Sarah's ass as they collapsed to the sofa. His mistress reached down and squeezed his eight inch erection as he slipped off her black lace bra.
Feverishly he sucked on her cantaloupe sized tits which had the largest dark brown areolas and Milk Dud nipples he had ever seen. They undressed each other with a fury as Sarah rolled her prostitute on to his back and slid his cock into her flaming cunt. Rick couldn't believe the energy of this 65 year old sex goddess as she always left him drained.
As Rick was being rewarded by the madam for a great fuck by being allowed to kiss her ass she reached to the table beside the couch and grabbed Mandy's file. She cooed to him, "I have a hot one for you. She has a really nice big ass and large soft boobies like you love and what's more she is a 35 year old virgin. She is yours if you want her. Here is the file on our unconquered lady."
Rick sat up and looked at the paperwork and thought Mandy might be fun to make love too. When he got to the pictures he licked his lips as Sarah was right she was just the perfect plumpness he loved to fondle. Sarah caressed his stomach as he asked, "So did you make a video of her visit?"
"Of course, I did sugar, here it is," Sarah pressed the remote control and Mandy's figure filled the television screen. Rick watched the video intently as Sarah went down on his cock. Rick was glad he had 12 hours until his next appointment as the older lady was draining him. He thought Mandy was sincere and sweet.
But, his worry was that she would try and back out. He saw the contract in the file so he knew one way or another he would get to pop her cherry. He was shocked when he heard Mandy say that she had never even had a tampon or dildo inside of her cunt. Seeing Mandy in her granny panties and plain white bra was too much for him and he shot a big load of spunk into Sarah's throat.
"Oh gawd, she is great; so innocent and so sexy! Can I do her tomorrow night? Oh you better see if anyone is available for enforcement of the contract as she looks a bit too nervous to me." Sarah looked at Mandy's calendar and told him it looked good to her but; of course, she would confirm it with the girl.
Then looking at Tom's schedule she told him that she would just schedule his rendezvous early enough that Tom could make sure that things were off to a good start before he met his lady. Tom's role was simple he would be nearby and help convince the girl that she had to make love with Rick or else. Of course, this was only needed with scared virgins.
Rick kissed Sarah on the cheek and left the details to her. Sarah Robinson whipped an Email out to Mandy reading, in part:
"Rick will be over at 8:00 tomorrow evening if that meets with your approval. May I suggest candles in your living room and bedroom and that you wear your sexiest dress or blouse and skirt. These things will put you in the mood. Also, you should have a bowl of fruit such as strawberries on your bedside table." Rick saw your picture and is really looking forward to your sweet date."
Time seemed to creep by all day long for Sandy. When the clock struck 6:00 she raced out of work and straight home to her computer. Opening her Email there it was a message from Mrs. Robinson. She smiled as she read it. She was surprised and relieved that it was so soon. She figured it would be four or five days.
She felt her muscles tighten and her heart beat faster. Taking a deep breath she answered the madam, "I will be here anxiously awaiting his arrival and will do as you ask with the fruit and such. Thanks in advance for everything."
Before she hit send she realized how much like a business note it sounded. She clicked send and now her only problem was making it through the next 25 hours or so. She had the most restless night of sleep she could ever remember. At work she had trouble keeping her mind on what she was doing. She kept envisioning the three pictures of Rick.
Excitedly she scampered home. Digging in the cabinet she found the candles and carefully placed them around the rooms and lit them. Dutifully she washed off the cherries and strawberries and sliced up some cantaloupe. She put the fruit bowl along with a can of whipped cream and a couple of smaller bowls and spoons on her nightstand.
There was still over an hour to wait. She realized that Sarah had suggested she do the candles and stuff to keep her busy but, she had flown around her place much too fast. Now, her nerves were getting the best of her. How could she let a strange man see her nude much less have sex with her?
She nibbled on some chips and paced the floor. Her brain was spinning and she was getting a stress induced headache. She wanted and needed to have sex but there must be another way. Maybe there was a friend after all. Mark was always nice and caring. No that wouldn't work because he'd tell Joe and Joe would tell his girlfriend and then the whole town would know that she had been a virgin until she was35.
Time slowly ticked away as Mandy thought about the whole situation. She was snapped out of her deep thoughts by a knock at her door. She was frozen in place. It must be him, it must be her hooker. She was in full panic mode now and thought she would piss in her pants. She couldn't move. He knocked again a bit harder.
Tom was out on the street and saw her silhouette run to the back of the house as Rick emerged from the door. Mandy was relieved as she heard footsteps walk away and ran to the phone and ordered a pizza from 'Virgino's' just around the corner. They would have it to her in 10 minutes as they already had a sausage pizza cooking.
Rick walked up to his coworker and Tom told him, "She is in there I saw her run away to the back of the house."
"I know I could smell the candles that she is burning. Looks like another virgin with cold feet. So, what do we do about her?" They discussed their options including forgetting it for tonight and confronting her on her way home from work the next day. Rick was afraid he wouldn't have anything left for that evening's appointment if they did that.
Still thinking the guys were just chatting when a pizza delivery boy rounded the corner. Perfect opening they both thought and nodded to each other. Tom walked up to the guy and paid him for the meal as Rick walked toward the house. Tom knocked on the door and yelled out that he had a pizza while Rick hid himself just out of sight.
The door opened and Tom's jaw dropped and he wished that whoever she was were his client. He walked into the door way and asked her for the ten bucks. As she went to get her purse Tom went to the middle of the living room and as she handed him the money Rick sacheted in right behind him closing the door.
"What the hell is going on here?" Mandy asked half knowing the answer as her heart was pounding through her chest and every muscle in her body had tensed. She looked for somewhere to hide but Tom had blocked her path to the back of the house and Rick was between her and the front door.
"Well Mandy Frederickson it seems I am your date for the evening and I am present to show you a nice evening as my employer promised you in the contract you signed," Rick tried to sound sweeter than the words he spoke and even smiled at her. He took a couple of steps closer to her sexy body.
"Who the hell is he?" she blurted out feeling like she could cry. She wondered what she had gotten herself into. There was no doubt she was at their mercy as they both stood about six feet tall and weighed around two hundred pounds.
"Well, Mandy Frederickson my name is Tom and I am just here to help my buddy Rick to convince you to fulfill your signed contract with Oak Street Secrets. I won't watch or even touch you if you keep your end of the bargain." Tom folded his arms across his chest waiting for the next move.
"You can't hold me to that contract It is a contract for an illegal activity and therefore unenforceable," Mandy was proud that she had thought of this. She even kind of smirked at Rick. Rick quickly grabbed her wrist and twisted it behind her spine.
"Mrs. Robinson has her own way of seeing to contract enforcement and you don't want to deal with her I can assure you of that. Now where's your bedroom?" Tom moved aside as Mandy meekly pointed to her bedroom. Tom had a seat in her living room and turned on the television pretty confident of Rick's success and eating Mandy's pizza.
Rick knew he had to accomplish two things very quickly. First he had to convince Mandy that he wasn't the devil. And secondly, he had to convince Tom that he had her 'eating out of the palm of his hand' by, at least, getting his hand inside of her clothes with in the next 15 to 20 minutes so Tom could go on his own date.
As Rick gently pushed Mandy onto the bed she couldn't believe that there was actually a man in her room alone with her. Rick shoved the door shut causing the woman to shudder. Then he grabbed both of her shoulders and pushed her back on the bed landing on top of his plump prize.
Mandy gasped half in fright and half in sexual excitement. Her 'date' roughly grabbed her face between his strong hands and almost violently kissed her. His tongue probed her mouth. He was so forceful that she couldn't help but open wide and let his tongue dance with hers. To her surprise she was kissing back even as she was trying, in vain, to push him away. She felt her body being a traitor to her as Rick spoke softly.
"Mandy you are so beautiful and sexy. I am so lucky to be with you tonight and I really want it to be a special evening for you if you'll give me a chance," he cooed as he ran his fingertips over her forehead and down to her ear and to her neck. Mandy shuddered involuntarily at his touch. He rolled halfway off of her caressing her side.