She sat back down on the bed and Debbie began to give her a back massage to loosen her up. Penelope could feel the heave of the older woman’s developed breasts against her back every now and then and she felt slightly ashamed of her own body. Perhaps sensing this, Debbie began to gently kiss her neck.
Penelope turned around and allowed Debbie to kiss her lips, to put her tongue on her tiny pink nipples. She felt Debbie’s hands sliding down to her bony hips and she tensed up.
Ignoring this, Debbie attempted to probe her vagina. Penelope did not shave, but her pussy was almost hairless, covered only in a few wisps of light blonde hair. Debbie put one of her fingers in her mouth, covering it in slippery saliva, and tried to insert it into Penelope’s tight pussy.
“Wait!” Penelope shrieked.
Perplexed, Debbie drew back.
“I’m sorry,” Penelope said. Tears began to stream down her face. “I’m a virgin, Miss. Brown. I’ve never had anything inside me before.”
Debbie smiled gently, lifted Penelope’s face towards hers, and kissed away her tears.
“You are a beautiful girl,” Debbie smiled. “I won’t break anything, I promise. Here, I’ll show you.” Debbie got up and went to the bathroom. She returned with a small mirror, she instructed Penelope to hold it angled towards her vagina. Debbie spread Penelope’s pussy lips, revealing a very small hole surrounded by tissue.
“That’s your hymen, sweetie. See how there is a small hole? Typically, you can fit a finger through there without breaking it, but since you are so small I won’t risk that when you aren’t ready.”
“Okay,” Penelope trembled.
“Why don’t you play with yourself for me, Penelope?” Debbie asked. “Do you know how?”
“I rub against my pillow sometimes, Miss Brown, but I’m not really sure what to do,” Penelope confessed.
Debbie explained the basic female anatomy to her, and showed her how to rub her clitoris and stroke the lips of her pussy. Penelope watched herself in the mirror as her tiny labia deepened in color and grew engorged. She watched as fluid dripped out between them. Her clitoris was growing; it was huge for her small size and peeking out from under its hood like a small penis.
Penelope blushed deeply.
“It’s weird,” she said. “It doesn’t look like normal.”
“You are just fine,” Debbie reassured her.
Penelope continued rubbing on her clitoris, and as it became erect it grew to the size of the end of a pinky finger.
“Lucky girl,” Debbie told her.
Penelope could not reply. She was out of breath and struggling to remain in control of herself as she watched her clitoris grow into a little penis before her eyes. She was horribly embarrassed. This was part of the reason that she had never lost her virginity, why she didn’t like to masturbate. She felt like a freak.
“Jerk it off,” Debbie commanded.
Penelope faltered.
Debbie repeated her command, moving Penelope’s fingers into position. Penelope began stroking her big clit, rubbing up and down on it like a tiny cock.
“It feels so good,” she exclaimed between heavy pants. Suddenly, her movements became spastic and she knocked over the mirror as she squirted out a stream of hot, thick cum all over the bedspread.
Debbie didn’t pause to let Penelope catch her breath before she took the girl’s clitoris into her mouth and began sucking furiously.
Penelope may not have lost her virginity, but she came at least a dozen times that night.
Chapter 10, Busted
When Debbie got to Hilton Head, she found the resort deserted. Despite the inviting weather and the shining sun, the parking lot was almost empty, as if a hurricane had come through and drove off all the tourists. Debbie walked to the front office with a pit in her stomach.
Inside the hotel was no different. The entry hall was vacant, and Debbie had to ring the bell several times before she could get a concierge to come up front and greet her.
“What happened to the big weekend event?” Debbie asked him. “Is it starting tomorrow? I was hired to cater a huge party, and I don’t see anyone here.”
The concierge waved her into a back office to speak with a manager. The manager informed her that there had been a last minute cancellation.
“We are so sorry for your trouble, and wish we could have informed you ahead of time. We got a call at the very last minute telling us that the event was off. They provided full payment for all of the services, and so we are more than happy to reimburse you for your troubles. Feel free to stay tonight, we have several empty rooms that have already been paid for.”
Debbie declined and headed back to D.C. with a feeling of resignation.
Someone must have tipped the ‘Bama Boys off, and there was really only one suspect. She was going to have to pay another visit to the horse farm.
PART THREE
Chapter 11, Just Waiting, Hands are Free
When Debbie arrived at the Whitehead’s private ranch, she found Madison tending to her prized stallion. She was combing its mane, applying ointment to its hooves, and cleaning up his appearance.
Madison informed Debbie that she had every intention of cooperating, but her stallion was show bound and she had a lot to do to get him ready for competition. Horses required a lot of maintenance.
“Would it be fine if we meet tonight, over dinner?” Madison requested. “I know somewhere very private.”
Debbie agreed and returned to her hotel to wait for a call from the young Miss Whitehead.
While she waited, Debbie masturbated casually. She thought about all the fine women she had been with during this mission. It was impossible to pick which encounter she liked best. They were all so enjoyable in their own unique way.
Debbie stroked herself lightly over her panties and imagined a big orgy with all the women she had met getting down and dirty. It might be a little much for poor Penelope, though. Thinking about the meek young girl getting totally turned out got Debbie feeling really hot, and she got off and then fell into a shallow sleep.
At 6:00 PM she got a text message requesting she make an appearance at a restaurant called Mercury in two hours.
Debbie went to the bathroom to get ready. She drew herself a piping hot bubble bath, wrapped her hair, and slid into the tub with relish. After soaking for twenty minutes, the bubbles had all but dissolved and Debbie set to work shaving her long legs. When she was done with this task, she drained the tub and turned on the shower. She always liked to rinse off after she had a bath to make sure there was no residue stuck to her skin.
In the shower, Debbie washed her hair and scrubbed her body until her skin shone. The shower had a handheld attachment, and Debbie thought it might be best to get off one more time before she met Madison. She let the warm water stream, aiming it at her clit. She gave in to her voluptuous feelings, rubbing her breasts with one hand and holding the shower attachment with the other. After she came, she turned off the water and toweled herself dry.
She blew dry her long red locks, and then put on a slinky black dress with an open back, high cut black underwear that accentuated her butt cheeks, and strappy black sandals. She applied dark red lipstick, eyeliner and mascara. When she was satisfied with how she looked, she called a cab and headed over to Mercury.
The restaurant had a very private feel. Thick curtains covered the large glass window panes that enclosed the restaurant, making it impossible for a passerby to see what was going on inside. She stepped in the restaurant, and noticed it was dimly lit, with the tables spread very far apart from one another.
Madison was sitting at the bar. She was in a body hugging red dress made out of some sort of stretchy fiber. It had a cut out at the cleavage area, allowing any passerby an eyeful of titties. Her long brown hair was in a French braid and she wore a brilliant gold necklace. Her makeup was impeccable.
She waved Debbie over to her, and they retired to a small table in the rear corner of the restaurant. Madison was d
rinking a Cosmo, and after Debbie placed her drink order, the two poured over the menu. They placed their order and made small talk as they waited to their dinner to arrive. There was no point to getting in a heated conversation only to be interrupted by a waiter delivering a dish.
Once their meal arrived and the waiter was out of earshot, Madison spoke.
“Look, Debbie. I know you think that I ratted you out to my father, but I would never do that. I don’t care about politics, anyway. I love the money and the lifestyle, but I am a down-to-earth, horse loving country girl at heart. I mean, look at me,” she said, pinching the fat just above her butt. “If I wanted to be a part of that lifestyle, I would need to lose fifteen pounds, at least. … Or just get lipo!” Madison let out a pretty peal of laughter at that.
Debbie waved her hand for Madison to get to the point. The girl’s figure was fine by her but she had no time for someone who was fishing for compliments.
“So, how did the ‘Bama Boys know I was going to show up at their resort?” Debbie asked Madison.
A guilty look shot across Madison’s face.
“To be honest, Debbie, my mother had a tracking device planted on you. She has also had several spies sent out to monitor your movements. You may have thought you weren’t being followed, but I assure you - her employees are good.”
Debbie shook her head in disbelief. So, she had at least one tracking device in her! But, to be followed like that? She thought it impossible. She had been trained better than that.
“That means your parents know I am meeting with you here now,” Debbie said nervously. “There aren’t any snipers with their sights aimed on me or armed thugs waiting to jump me when I leave the restaurant, are there?”
Madison shook her head.
“I can’t tell you more,” she said. “You need to visit my mother. Things may not be as you think.”
Debbie let out a long sigh. “Enough with all this intrigue,” she thought. “And enough with all this travel!”
Madison told Debbie that her mother’s mansion was in Huntsville, only a short drive from Fort Payne.
“I recommend you spend the night here, and then set out tomorrow morning,” Madison advised. “Now, let’s enjoy our meal!”
Madison dug into her pasta carbonara, but Debbie had lost much of her appetite. She nibbled on her salmon but focused more on her drink. When the waiter came back to collect the plates, Debbie’s was only half-eaten. She declined a dessert, and the waiter returned with a vodka tonic for her and a slice of chocolate cheesecake for Madison.
As they exited the hotel, Debbie was feeling the liquor and exhaustion get to her. When Madison suggested she forgo the cab and drive back to the ranch with her, Debbie agreed.
“No horses though,” Debbie said. “I’m not into that.”
Madison agreed. On the car ride back she told Debbie that she had been thinking about what she had told her the last time they met.
“All that stuff about finding a good lover that appreciates me. You are right. I have a deep bond with my stallion, but it isn’t the same as being with someone who can talk to me, provide for me, and fall asleep in bed with me,” she told Debbie.
Debbie put a hand on top of hers and smiled.
Chapter 12, Big Girl, Big Fun
Madison’s bedroom was decorated in what Debbie would have described as a rather immature style. Her bed had a fluffy pink comforter and a white lace canopy with pink ribbon trim. There were stuffed horses and horse figurines everywhere.
Debbie sat down on the bed and watched Madison undress. She took her clothes off, but kept on her gold necklace and heels.
“Do you really like my body?” she asked as she exposed her voluptuous breasts.
“You are truly blessed to have such ample assets,” Debbie answered honestly. “Not to mention you healed quite nicely from that beating I gave you last time.”
“I get scraped up and scratched all the time riding horses,” Madison told her. “Besides, you don’t think I have had my fair share of bruises with a stallion for a lover?”
Debbie supposed that must be true.
“I liked being tied up and beaten,” Madison told her. “But I do have a show coming up, and I want to be in peak condition. Let’s keep it more gentle this time?”
Debbie agreed.
“I want to lick your pussy,” Madison told her.
Debbie removed her underwear and let Madison go to work. Madison got on her knees at the foot of the bed and started eating Debbie’s pussy like it was the most delicious piece of chocolate cheesecake she had ever had. She ate hungrily and sloppily, spittle and juices dripping down her face and landing on her giant tits. Debbie enjoyed watching Madison’s bosom shake like jello with each move of her head, and she loved the feeling of Madison’s hungry mouth on her genitals.
After Debbie got off, she had Madison lay down on the bed.
“I’m going to show you something,” she told Madison. “It may not be a horse cock, but it’s the next best thing,” she laughed as she shoved her first deep into Madison’s gaping pussy.
Madison squealed in delight, she wasn’t squeamish at all. She let Debbie pound her hard and fast with her fist, going in deep. Madison’s pussy seemed endless. “That horse really did a number on her,” Debbie thought, opening and closing her fist inside the girl.
Debbie’s arm was covered in a thick cream, but Madison still seemed some way from climax.
“Does it feel good?” Debbie asked her.
“It feels great. So full, fuck me harder,” Madison cried.
Debbie complied, and she rolled Madison over onto her side, and stuck three fingers in her ass.
Madison moaned in approval. This is what she needed, to get pounded from both ends.
Debbie stuck a fourth finger in Madison’s ass, and with the next pump of her hand she slipped in her thumb. Now she was double-fisting Madison, with one hand in her pussy and one in her ass. She alternated powerful thrusts, feeling herself deep in Madison’s stomach.
Madison’s eyes were wide open and had a glazed, dreamy look. She had lost herself in the penetration and in the stinking smell of dirty sex — pussy cream and fecal matter. She showed no evidence of being embarrassed about what a dirty slut she was, she just screamed for more.
Finally, when Debbie thought she couldn’t take it anymore and was going to collapse from sheer exhaustion, Madison came. Her cum was heavy and sticky, and a cream white in color.
“You really cleaned me out good,” Madison noted, and then fell into a deep sleep.
Debbie collapsed next to her and the two slept for several hours in the dirty sheets.
The next morning, Debbie woke up and took a long, hot shower. She cleaned Madison’s residue from herself, washing until she felt fresh and smelled great. Madison gave her a ride to her hotel room, where she collected her belongings and set out for Huntsville.
Chapter 13, Show Down
Debbie pulled up to a gigantic mansion. It was just one of many in the wealthy development, but it was by far the biggest. The garden was well-manicured, and Debbie saw two groundskeepers tending to the plants.
She walked up the marble steps to a heavy oak door. She knocked politely, and when that elicited no response she tried the doorbell. Still no answer. Debbie tried the door knob, and the door was unlocked.
“Hello,” Debbie called, as she cracked open the door. “Is anyone there?”
Her voice echoed through the giant entryway.
Debbie climbed up the grand staircase in front of her, and was greeted with a hall of doors. She stopped at each one, putting her ear to the door to see if she heard anything. When she got towards the end of the hall she saw there was a set of double doors that were open.
She entered the doors and into the master bedroom. A bathrobe was laid out on the bed and she heard the sound of running water.
“Hello?” she called again.
Still no answer.
Debbie crept into the bathroom. It was b
eautiful, finished in green granite. She saw the figure of a woman in the large, steamy shower. The lady was humming a tune to herself.
“Hello? Is that you Mrs. Whitehead?” Debbie asked.
The humming stopped, and she heard the squeak of the shower being turned off. The glass door opened, and steam billowed out. Mrs. Whitehead came along with it.
Debbie’s jaw dropped when she saw Mrs. Whitehead’s body. It looked nothing like what she expected for a woman going on seventy. There was no wrinkles or sags, no loose skin to be found. If she hadn’t known better, Debbie would have guessed she was closer to thirty.
“Well, don’t just stand there,” Mrs. Whitehead said. “Hand me a towel please.”
Debbie did as she had been instructed, and she watched as Mrs. Whitehead toweled off slowly and seductively.
“Please, call me Patricia,” she told Debbie, shaking the water from her hair.
“Fine with me,” Debbie told her.
“My, aren’t you the fox,” Patricia teased her. “With that beautiful red hair. A real classic beauty, you are.”
Debbie thanked her, but she was not about to let her guard down. Patricia had known she was coming, Debbie wondered why she wasn’t more prepared to greet her.
“You will have to excuse me,” Patricia told her. “Madison told me you were coming, but I didn’t expect you to be here so early. You made great time.”
“I drive fast,” Debbie replied tersely. “But you probably know that already if you have a tracking device in me.”
“Yes, you will have to forgive me for that. You see, my husband suspected that Harriet would get involved in the governor’s campaign long before you became involved. She is Miss Melton’s lover, after all. My men have been following you for some time. We know you are her top spy. When you were out in Rodeo Drive enjoying sushi with that pretty young thing Natasha, your server slipped a small nano-device in your drinks. You didn’t think that Harriet was the only one who possessed that sort of technology, did you?” Patricia laughed. “You see, my company PHM Technology manufactures all sorts of products that you would be familiar with in your career as a spy.”
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