Valentine's Day

Last year Wade took Madison in a limo to a fancy french restaurant. It was the nicest Valentine's day she'd ever had. Their second Valentine's day as a couple was fast approaching and she wanted to do something really special. Valentine's day is usually focused on women and she thought it would be really nice to focus this day on Wade.

Madison was a foley artist. She was 5 feet and 6 inches. She liked wearing six inch heels to push her height to 6 feet, but she usually only wore 3 inch heels outside of work. At work she had to wear sneakers. Foley recording often required a lot of movement, some of which was awkward. Madison's weight was always within 10 pounds of 145. She had light red hair, that sometimes looked strawberry blond. Her hair went a little passed her shoulders. Her hair was all the same length. Madison had pale skin that came from her Irish grandparents.

Wade was an architect. They had lived together in Wade's house for a little over a year. It was perfect because her lease was coming to an end just when their relationship started to get serious.

Wade was really honest with her, and told her about his interest in ponyplay. Madison had seen The Secretary so she had some idea of what it was when he told her. She had never done any BDSM, which had made it intimidating for Wade to discuss with her. As their relationship blossomed she learned more about it. She subscribed to a Yahoo Group for a website called SirJeff's PonyGirls. She also found some websites with ponyboys, and decided they seemed fun to play with.

She decided that for Valentine's day she would be his ponygirl. On New Years day she started looking for tack shops. They lived together in Lakeville Massachusetts. The closest tack shop she could find was in Springfield. The shop's website said that customers could come in for private fittings. She was nervous to call the store. She had read some stories about women being abducted, but she knew they were fiction. She also hadn't spent much time naked around strangers, and this stranger would be fitting her into pony tack! As she contemplated it she realized she had to act soon or she would lose her nerve. She dialed the number in her cellphone.

After ringing twice a man's voice said, "Tony's Tack Shop, how may I help you." Madison blushed, this was it. As she tried to think of what to say the man asked, "Hello?"

"Hi, I'm calling to schedule a private fitting." Her emotions were suddenly overwhelmed with a feeling of vulnerability.

"Okay, we're available most nights. Is there a specific date you had in mind?"

Wade was going to be on a business trip in a week, it was the perfect time. "How about the 10th?"

"We can take you on the 10th. How does 7PM sound?"

She wondered if he meant to use the word take. "That works, that will give me enough time to eat and drive to your shop."

"These usually take two hours. Will you have enough time?"

"Yes." If he was worried about her time than it seemed unlikely he'd abduct her, that was a relief.

"Great, what's your name?"

"Umm", she hesitated. Saying her name would really make it a more public action. Even if he had caller ID, which he probably did, she could be using anybody's phone. She took a deep breath and let it out slowly, "I'm Madison."

"Okay Madison, I'll see you next Tuesday at 7." The phone disconnected, he had hung up. She was blushing again as she realized that this man, who she didn't know, knew she wanted to be tacked up as a ponygirl, and would see her before the fitting. In fact, maybe he would be the one to fit her for the tack! It was probably a small shop, would she be fitted by a man?

This had her really worked up. Wade was in his office getting some work done. It was almost lunch time. Since it was a holiday they would certainly have time for a nooner! She walked in and he was using a computer aided drafting program. She was bare-foot, and the rug had muffled her steps. She walked behind him and started massaging his broad shoulders. He felt a little tense, he definitely needed a break! His shoulders relaxed as she massaged them. He was still working when she finished massaging his shoulders. The desk was wide enough for her to duck under, which is exactly what she did. She decided it would be best to get straight to the point. She unzipped his pants and pushed aside his boxers. He was still pretty soft, but clearly she had made some impact. She pulled his cock out and caressed it for a moment. She than put her lips to the top of his cock and kissed. There was a slight taste of urine on it.

She opened her mouth and took him in as deeply as she could without gagging. His penis swelled, soon reaching it's full-size. She bobbed up and down on it while holding the bottom of his cock with her right hand. After a few strokes she would take him out of her mouth and lick him like a popsicle. She blew on his penis and than took it in her mouth again. She repeated this for a few minutes until he finally put his hand on her head. This was as close to BDSM as they ever got. He would hold her head by the hair. He pushed her mouth up and down, but never so far as to gag her. She still held onto his shaft with her hands, excited that she'd really gotten his interest. She knew she'd be getting fucked soon. Between the phone call and the thought of Wade inside her she was getting really wet. When Wade neared an orgasm he pulled her head off his cock, pulled her up and around to kiss him.

She loved that he'd kiss her after she had given him a blowjob. While there wasn't much pre-cum in her mouth, it was enough to turn off some of her former boyfriends. Wade was so hot. She pushed his chair out a bit and lifted her dress.

She was quickly on him. He felt great. He was the perfect size for her. She used to have a dildo that was slightly smaller. Their relationship had rendered it worthless. As she rode him, his cock slamming against her g-spot, he unzipped her dress. He pulled it off her arms. Her breasts were only a size B-cup. She was a little embarrassed by how small they were, but Wade seemed to love them. She wasn't wearing a bra, it's not like she had anything to sag. He took her left breast into his mouth. It was slightly smaller than her right breast. His mouth was so hot. His tongue went around her nipple. Than he sucked on the nipple hard just as he slammed into her. It was too much, she wanted to hold off the orgasm but she couldn't. She leaned forward so her clitoris would rub against him as she started to tremor in orgasm. Her vagina tightened on his cock, but he was still going.

When her orgasm finally ebbed he stood up holding her. He walked with her still impaled to the closest wall and leaned her against it. He unbuckled his shorts and pulled them down. He didn't mind having sex clothed, but when he was going to cum he didn't like clothing around his crotch. After his shorts fell he pulled her dress up and off. He was ready. He starting thrusting using his hands to lift her after each thrust. His pace was a little faster than hers. His breathing was getting heavy. He started kissing at her neck. It felt great. Finally he started to cum. She was close to a second orgasm and clamped down on him as much as she could. She could feel him exploding inside of her. As the last of his cum spurt into her she started to cum. He kissed her on the mouth. He loved to kiss her just after he came. He looked deeply into her eyes.

As they both began to get their breathe back he backed up. He had gone limp and simply fell out. She could feel his cum drip out with him. He placed her on the ground and said, "Thanks, I needed a break."

She smiled and said, "You're welcome. I'm glad you needed a break because I needed that. I've been planning something for Valentine's day, and it got me really worked up."

"I see, should I ask what your planning."

"You can, but you won't get anything out of me, except to say that you better keep that night open for what I'm planning."

****

It seemed like time went very slowly waiting for the fitting. Like most work days, she was wearing blue jeans. She was also wearing a purple turtleneck. Sometimes the materials she worked with to make sounds were messy. On the day of the fitting they were nearing the end of a project and some of the recordings had been rejected by the studio they were doing contract work for. The day was a hectic blur of re-recording based on the studio's comments. It was good that they day was busy, because it gave her a break from thinking about ponyplay. She even had to work a little late. She went straight to the tack shop, she didn't have time to eat. Fortunately, the Massachusetts' Turnpike had fairly light traffic.

She still had a healthy amount of paranoia. She left two letters at home for Wade in case she was abducted giving all the details of where she was. He would be home in a couple of days. The first letter was on the kitchen counter. She hid the second letter under his pillow, just in case she was abducted and forced to reveal the location of a note. She also had her smartphone on her, so it might further help track her. She didn't think she had to worry, but it was good to be protected.

When she arrived there were only two cars in the parking lot. She locked her car. She slipped her keys into her right pocket. She always kept her phone in her left pocket and her keys in the right pocket so that the keys wouldn't scratch the phone's screen.

There was a display window next to the door. You couldn't actually see inside the store from the outside. The display blocked the entire window.

When she opened the door she instantly smelled leather. There was a man sitting at a high-end sewing machine that could handle leather. He was working on with some leather that was died pink. The wall on her left had a counter and cash register. The rest of the room had various articles on displays. Some of the items were on mannequins. The left wall was covered with professional photos of ponygirls and ponyboys. The photos were clearly a brag sheet for the custom work the store sold.

When the door closed behind her it caused a bell to ring and he finally looked over. He had short curly black hair and a mustache. He was clearly Italian. "Are you Madison?"

She blushed. Of course he would be expecting her, he was probably the man he talked to. "Yes she said", as she forced a smile.

He stood up and walked over with his hand outstretched to shake hers. He was a little shorter than her, maybe five foot two. He was muscular too. Some hair was at the top of his shirt. He reminded her of Mario from the Nintendo!

They shook hands and he said "I'm Tony."

She blushed a little again realizing he was the owner. "Nice to meet you. What should I do now," she said trying to sound brave.

"I need you to sign a consent form. We need you to be naked to get the correct sizes and this covers us from lawsuits."

He gave her a paper that was in a stack on the checkout counter. She started to read it. It said:

I hereby consent to the activities that occur within a fitting at Tony's Tack Shop. For the fitting I agree to be nude in order to insure a proper fit. I agree to wear bondage similar to what I might later buy. The store will not take any photography of without also signing a separate consent form. I agree to allow at least one employee see me naked during the fitting...

There was a lot more, but she got the idea. Tony handed her a pen and she signed and dated the form.

He smiled and said, "follow me, I'll show you where to get ready."

As she followed him through a door in the back she patted her left pocket to be sure her phone was there. The room they entered was smaller, about the size of a bedroom. It looked more like a stable though. The floor had a mixture of wood chips and hay. The walls where all dark brown wood. Under the wood chips there was concrete. There were a few wooden chairs. A large set of cabinets covered the far wall.

In the center of the room was a sawhorse that had been modified by padding the top with a large cushion. The feet of the sawhorse were secured to the floor with steel plates. There were metal rings on the legs.

Tony said, "leave your clothes here," pointing to a chair. He went back out the door and closed it behind him.

This was it. She needed to get undressed to be fitted. She could still back out. She untied her shoes and took them off, neatly placing them on the chair. She put her socks in her shoes. When she held the bottom of her shirt she hesitated because she had no bra on. After a pause she took it off and folded it, stacking it neatly on her shoes. Then she pulled off her jeans with her panties. After folding her jeans she stood there for a minute waiting for somebody to arrive.

The door opened and Tony came in. She blushed, she had been expecting a woman, but it seemed pretty obvious he was the only one who worked here.

"Ready?" he asked.

She nodded, knowing that Wade was worth whatever minor humiliation she would have. Tony kept his eyes on her face. While she wasn't gorgeous she appreciated it. Despite her average looks she did at times meet men who couldn't get their eyes off her breasts.

Tony opened a cupboard and took out a notebook and four cuffs. He put the notebook down and said, "lets begin."

She took a deep breathe and nodded. He started by putting a cuff on each wrist. The cuffs had numbers on them indicating her wrist size. As he wrote the sizes down he said, "You'd be surprised how many people have different sized wrists!"

Tony repeated the process with ankle cuffs. Madison found it a little weird to have him bending in front of her naked body to put on the cuffs for her ankles.

After he wrote down the ankle sizes, Tony took her left hand and led her to the sawhorse. He said, "I need you to lie down." Tony waved his hand over the horse indicating how she should lie on it.

She bent nervously, laying her torso on the cushioned horse. Tony took her left wrist and attached the cuff to a leg. She hadn't expected this. As she thought about her situation he quickly secured her other wrist. She nervously waited to see what would happen next.

Tony moved behind her and attached her ankle cuffs to the horse. Clearly there was no escaping now. She tried staying calm, remembering the precautions she had taken.

Tony was making some sounds in the cabinets. They were directly behind her, so she couldn't tell what he was doing.

"I always like to get the worst part over first," he said. "I'll start by fitting you for a tail."

She felt his hand touch her vagina. He slowly inserted a finger. She realized that she was wet, which surprised her because of how nervous she was. His finger pulled out and than she felt some cold metal press inside. The metal moved around getting some of her juices on it. He than pulled it out and parted her cheeks. She unconsciously clenched her rectum.

"Relax," he said. "This is the smallest size."

She tried to relax, but it was no use. This was too far beyond her comfort zone. She felt it press at her anus. It pushed through and popped into place. It didn't hurt, and she eventually relaxed. He pulled it easily out and she heard him set it down. Again, she felt cold metal at her vaginal entrance. He pushed it in, repeating the process. It did feel bigger, but small compared to Wade. When he pressed it against her anus she was able to relax. It went in easily.

He pulled it out of her. The third plug was still smaller than Wade. She doubted that it was big enough to make her cum. Again, she was relaxed as he pushed it into her anus. He slowed as the widest part reached her sphincter. It hurt as it pushed through. She cried out briefly as she winced from the pain.

"Are you okay?"

She took a deep breathe and said, "yes." She felt like it filled her. It was comfortable once it was in.

"This one is your current size. Over time you can develop to take larger sizes. I have a training kit you can buy."

She wondered if she'd ever be able to take Wade's size. The training kit sounded good, but she didn't have the concentration to think.

When she was ready he pulled it out. It was almost as painful to take out. It was clear that it could only be taken out by pulling it out.

"This is good," he said relieved, "you're my size."

She wasn't sure what he meant, but she didn't care. She was trying to recover from the pain.

There was a sound of some kind of liquid. He was probably cleaning his hands. Than he felt his hands again at her anus. He felt something thrust in. It was about the same size as the plug, but the shape was different. He grabbed her hips and held on as the new object thrust in and out.

"What are you doing?" she asked.

"Sorry, I need to get my concentration back so I can finish your fitting."

She was shocked. He was fucking her. He was taking her anal virginity.

"Stop," she said. "I didn't agree to this."

He sighed, "Yes you did, didn't you read all of the consent form? It says I can have any sex with you except vaginal sex. That is reserved only for those your owner consents. Also, as it stipulates, I have a condom on and I was found clean of STDs last week."

She hadn't read it all, how stupid. This was similar to situations she had read about. What else did it say, she wondered. "Please stop-" he cut her off with a slap on her ass.

"Hush, the fitting is easier if you aren't gagged."

Her face flushed red with humiliation. He continued to thrust for awhile, and then paused. He moved his hands to fondle Madison's tiny breasts. Her nipples were erect.

His right hand moved to her clitoris, which was hard. He began to rub it.

She had been raped once by a friend who was drunk. It had felt good, but it was horrible. She hadn't consented. He was so drunk he didn't even cum.

The rape had been after a college party. She was friends with the host, so she had stayed after to help clean. She fell asleep on his couch and woke up to find him on top of her. He had lifted her skirt and was pushing her thong aside. Madison had told him no. She struggled to get him off her but he was too heavy. She liked him, but she didn't want to have sex. She'd only been with a few men. He didn't have a condom. She was dry, which made it hurt when he entered her.

Consent is sexy. Wade always respected her right to say no. When she said no, Wade never argued. Sometimes his acceptance was so sweet it turned her on and she changed her mind!

This was different from rape. She actually had consented. While it was humiliating, it felt good. Tony was actually trying to get her to cum. As she warmed up to it he began thrusting again. It felt great. It wasn't Wade, but it was so different from anything else. She felt it building up. She began to shake. As she came he thrust faster. As her orgasm crested he thrust deeply and began to cum. His breathe was ragged as he made three deep thrusts.

He pulled out of her. Madison listened as he cleaned up. She could her him washing something. When he returned to her he again thrust a plug into her vagina. He than inserted it into her anus.

"It fits better now," he said. "Do you want your tail to match your hair of should it be horse hair?"

She struggled to think about what he was asking and put aside what had just happened. "I want it to match my hair."

She felt her hair pulled back and than heard the sound of scissors. He had just cut her hair! It was probably shorter than a pony tail now.

She felt like she was going to cry. She was in an emotional stage of shock. She took deep breaths to relax herself.

He walked in front of her and began touching her neck. She noticed a collar in Tony's hand just as he put it on her. When he stepped away she asked, "do you fuck all your customers?"

"Just the ones that turn me on."

She blushed. "What if I wasn't your size?"