Jenny and John Ch. 03

"Well it seems there is a clear winner." Jenny announced holding the condoms up for John to see, each with a substantial amount of clear liquid. The order was clear. Outfit 3 won followed by outfit 2. To John's surprise, condom 3 had almost double the precum as condom 1.

Jenny admiring the condoms said, "John this is very impressive, this has helped me make up my mind on an outfit. But now there is one more part." Jenny let her voice trail off as she retrieved something from behind John. Jenny procured a martini class that she set on the table as she continued to explain, "Now John, what I haven't told you is that dinner tonight is a date with my friend Mark." John looked stunned but was unable to protest through his gag.

"You have two options for how the night will go." Jenny said in a slow methodical manner, building suspense. "You can either join Mark and I as my sub or you can stay home as I go on the date alone. Understand that if you come with me, I'll choose your outfit and you'll speak only when spoken to." As Jenny explained this to John she had untied each condom and poured the accumulated precum from each into the martini glass. Holding the glass up in front of her, swirling the precum, Jenny continued, "If you'd like to come along with me on my date then you'll drink the precum when you're uncuffed. If you don't drink or you don't finish the glass within a minute you'll be staying home in the cage. Say nothing, simply drink or don't, the choice is yours."

Jenny, still dressed in her third outfit, moved behind John and removed his ball gag and uncuffed him. John's mind raced "I don't want Jenny going on a date with some guy without me! But that is so much precum to drink. Who is this guy? What did she mean 'she'll dress me?' How could I let her go? I just want to be with her. I want her to show me off as her sub."

As the cuffs were undone John's mind quieted. Without consciously making up his mind, he dove for the glass. John began drinking it as quickly as he could but soon found his mouth full. Thankfully this was not the bitter flavored cum but the more sweet, mostly salty precum. John convinced himself to power through, ultimately downing three mouthfuls of precum.

Jenny's soothing voice called to John, "Very good, I'm so happy you made that choice." Jenny ran her fingers through John's hair as she praised him. John beamed in the glow of making Jenny happy, "Thank you, Mistress."

Jenny commanded John to remain knelt where he was as she went to change back into her robe. Jenny went on to explain to John that it was just about lunch time and since it is a meal at home John could get dressed if he wished and they would eat.

John put the provided gym shorts back on but opted to remain shirtless. The two then proceeded up from the dungeon to the kitchen. There they had a simple lunch of cold cut sandwiches and some fresh fruit.

As they sat and ate John recalled that the rules are relaxed at this time and decided to press his luck with a question. "Mistress, who is Mark?" Jenny with a slight grin replied, "I'm so glad you asked. Mark and I have been long time friends, often with benefits." John looked down slightly as he muttered, "I see."

Jenny, looking to reassure John continued, "John, I am a woman who knows what I like, as I am sure you have gathered. Just because I enjoy Mark's cock does not mean I don't enjoy my time with you. We have had a lot of fun over the last day, wouldn't you say so?" John looked back up and nodded, "Yes, Mistress. You have brought me more pleasure in the last day than all of my previous girlfriend's combined."

Jenny, saw her next move, "And of all these experiences, what stands out the most?" John thought for a moment, "Mistress, the pegging and the Sybian ride."

Jenny had him. She knew now that with the right push John would do anything she said. "Interesting you didn't say fucking me yesterday. See, we can have even more fun than regular vanilla sex. Even now that you know you were helping me to get ready for a date you admit that it was one of your favorite experiences. Just because on occasion I need my pussy stretched by a nice thick cock doesn't mean that you and I will have any less fun."

John thought for a moment, "She is right. I loved helping her pick out a sexy outfit even if it was for a date with another guy. While fucking her was great she is right, I named other experiences as the highlights. I guess she is right, there is no harm in her doing this if we enjoy other activities."

Jenny had John caught in her web. He was now convinced, "Yes, Mistress. You're right, I guess we are enjoying other things besides vanilla sex." John sounded sure in his statement but not confident.

Jenny saw that John just needed one last push, "How about a deal John? If you are a good boy for me on my date tonight, I'll let you feel my pussy again."

Immediately John cheerfully replied, "Yes Mistress. I would love that. I promise I will not only behave myself, but I will do my best to be a pleasure to be around during your date."

Jenny smiled, cooling John's nerves, "Wonderful. Now it's an early dinner since we'll have a late night so let's get ready."

John cleared the plates as Jenny retrieved outfit three and John's buttplug from the dungeon. Jenny led John up to her room to two side by side make up stands within Jenny's walk in closet. Not thinking much of it, John removed his shorts, reinsterted the buttplug and sat at one when instructed by Jenny.

Jenny explained that she would lay out some clothes for John to wear but that he would patiently wait for Jenny to get dressed and do her makeup first.

Jenny donned outfit three again as John looked on. Again he started to leak from his cage, though this time it was not nearly as much without the anal stimulation.

Once Jenny was dressed again she began her makeup. This was a time intensive process that John observed. While not sexually aroused by the application of the makeup John was more than happy observing Jenny as she applied it.

As Jenny put the finishing touches on, she turned to John and asked, "How does it look?" Jenny looked stunning. She has applied a full face of makeup from foundation and blush to eye makeup to lipstick.

Her lips wore a glossy red lipstick that looked like it's only purpose was to be smeared over the shaft of a cock. Jenny had light pink eyeshadow to match her skirt and jacket as well as precisely drawn winged eyeliner. With a hint of blush and false lashes applied she looked like perfection.

"Mistress, you are the most beautiful person on the face of this planet." Jenny beamed, "That's a good answer." chuckling as she replied.

Jenny's face turned more serious but not cold as she said, "Now John, it is time to get you dressed." Jenny brought over some folded clothes as John thought it was odd that she would have men's clothes.

Jenny laid out a pair of khaki pants as well as a light blue button up blouse. Then on top of the pile Jenny set a white lace bralette and pantie set. John's face dropped, speechless he turned to Jenny.

Warmly, cupping her hand on John's cheek, Jenny said, "John I've had such a good time turning you into my little slut that I've decided I want you to dress a little more feminine for me. We are going to start slow with an outfit that most people would simply ignore if they didn't look twice."

John was nervous, he'd never worn women's clothes before let alone in public. As John's initial shock disappeared Jenny asked, "What do you think? Will you be a good boy for me and wear this outfit?"

John put together the words in his head before responding, "Yes, Mistress, I will. I want to be good for you, I've just never worn anything like this before. Going in public makes me a bit nervous."

Jenny, noting that John was nervous to go in public but had no objection to actually wearing the clothes, was quite pleased. Jenny reached in and hugged John. "I'll be right there with you. I won't let anything happen to you."

John's whole body relaxed in the embrace as Jenny's soothing voice offered support. As the two parted John took a deep breath, "Ok, Mistress. I'm ready to get dressed."

Jenny smiled as she picked up the panties. She helped John step into them and ensured the fabric was snug around his cage. Jenny then grabbed the bralette and had John turn so that she could help secure the clasp in the back.

Jenny was very pleased with how the lace thong panties were swallowed up by John's ass. As the clasp secured John picked up the blouse from the table as he put it on he noticed the material was far softer than any men's button down shirt.

John found that the sleeves were rather loose as is often the style for women's sleeves but opted not to complain. John was rather surprised at how much he struggled with the buttons being on the opposite side as he carefully secured the shirt.

Jenny stepped in as John was doing the last of the buttons, "Not that one. Leave the top two undone." John complied even though he would never choose to wear a shirt that way.

John then slipped on the pants and found that they were quite fitted. They hugged his ass and thighs quite tightly but had a very slight taper down toward the bottom. He noted that they stopped just above his ankle but again decided not to complain.

As John realized there were no pockets on these pants he was handed a thin white leather belt. Clearly a women's belt he found it quite easy to pass through the belt loops. To top off the outfit Jenny handed John a pair of women's white flats.

John hesitated, "But Mistress, people will surely notice these." Jenny, with a kind look in her eye said, "But isn't that risk worth it to be my good boy tonight?"

John's cock twitched at 'good boy.' He wanted nothing more than to please Jenny. Without further question he put in the flats.

Jenny praised John's bravery as she guided him to the makeup table. As Jenny sat him down she explained, "Now, I am going to do your makeup but it will be very subtle, so sit still and be quiet."

Internally John protested but did not want to disobey Jenny. John sat silently as Jenny applied very light makeup all over John's face. Jenny also plucked John's eyebrows, shaping them to be more feminine.

As Jenny finished she spun john around to look at himself in the mirror. Surprisingly, he found that he didn't look all that much different. He looked almost as if a filter had been applied.

John examined closer, finding that a layer of very light foundation had been applied, almost unnoticeable except that it covered some minor blemishes on his face. Jenny had applied mascara to John's eyelashes but again, they simply appeared longer and fuller, not necessarily feminine. Jenny had decided not to push it with eyeliner or eyeshadow this time leaving a more natural look. Finally John saw that he had clear gloss applied to his lips. Quite subtle, his lips simply had an extra shimmer rather than any color to them.

Ultimately, John found nothing to object to. He certainly would not have put makeup on himself but if it were to please his Mistress he was not upset with how it came out.

Jenny cheerfully exclaimed, "Oh John! You look so pretty!" Despite John being caught off guard by the choice of 'pretty' he was nevertheless happy to receive praise from Jenny.

"Ok, we certainly took our time getting ready but I think it's time to go now." John was shocked, they had spent the whole afternoon getting ready and it was quickly approaching dinner time.

Jenny in her heels and John in his flats made their way to the garage to get in Jenny's Porsche. The restaurant was not far and conversation mostly included Jenny's discussion of how much he has enjoyed training John's ass.

As they pulled up to the restaurant the valet took Jenny's car and ushered her and John into the restaurant. The interior was dimly lit but very obviously fancy. "Jenny Clarke, party of 3." Jenny pleasantly replied when asked for the name on the reservation.

As the two were led to their table Jenny took John's hand but was sure to keep a step ahead of him. John couldn't help but chuckle as Jenny so effortlessly asserted her natural dominance.

Jenny and John sat for a few minutes reviewing the menu as they waited for Mark. "Anything catching your eye John?" Jenny asked. If John didn't know any better he would never have assumed Jenny was a domme from that statement. John, with a lowered voice replied, "Yes, Mistress, the salmon looks very good."

As the two chatted about their choice, Jenny felt a hand on her shoulder. "Mark! It's so good to see you! How are you?" Jenny exclaimed.

Mark was a well dressed, quite tall, black man. John guessed he was about 6'2" and if he was being honest, John couldn't help but notice that he was very handsome. Dressed in tailored jeans with a white button down and a sport coat Mark looked very nice. He has short hair and a full beard that were well manicured.

"I'm well Jenny, it's so good to see you too!" Mark replied as Jenny stood so they could share a hug. Mark snuck a kiss on Jenny's cheek that John was not overly fond of but chose to ignore in favor of being a 'good boy.' "And who is this?" Mark said, moving toward John. John stood to greet Mark as he was pulled in for a hug. To John's surprise he too received a kiss on the cheek.

"That's John, my new boyfriend." Jenny explained. Boyfriend. John's stomach did a flip. The hesitance John felt from the clothes and the makeup immediately left him. All he could think about was 'boyfriend.'

"Well John, it's very nice to meet you." Mark said as he slid in the booth next to Jenny. The three of them discussed what they would order for some time until the waiter came over.

"Are we ready to order?" The waiter asked looking at the three sat in the booth. They all nodded in unison. "Well then, let's start with the lovely lady. What will it be?" Jenny ordered the house salad and before the waiter could take the next order the continued, "and he'll have the salmon." Indicating to the waiter it was John's order.

John couldn't help but feel submissive in that moment but he loved it. Jenny, this elegant woman taking care of him while on her date. Mark ordered his food as John was enthralled by this feeling of submission. Then the conversation returned.

"So Jenny, John is your new boyfriend? Is he submissive? I know how you love your boy toys." Mark chuckled. John was taken aback at such a forward question.

Mark put his arm around Jenny as she responded. "Oh yes, I'm still breaking him in but we are having a lot of fun." Jenny replied, her attention exclusively on Mark.

"Well John, you'll have a lot of fun with her if you just do as she says. I promise." Mark stated with a knowing inflection. Returning his attention to Jenny he continued, "So is he caged yet?" Mark asked.

Jenny eagerly replied, "Oh yes, he's caged and plugged right now. He's also wearing makeup and crossdressing right now." John was shocked at how forward Jenny was. She was stating this at normal volume with no care as to who might hear.

"I thought he was rather pretty. I totally see it now. You've always got good taste in fashion and makeup." Mark commented. John couldn't help but wonder if he was intentionally phrasing these questions to make John wonder how many subs Jenny has before him.

From there the conversation shifted to small talk until the food came out. The trio ate rather quickly, no doubt in anticipation of the rest of the night.

As the plates were cleared and Jenny paid the bill she turned to Mark and asked, "So did you drive here and you'll follow me home or what?" John paused slightly as they walked out, the plug still massaging his prostate with each step. Although the plug was not the cause for the hesitancy. John wasn't surprised that Jenny meant a date that continued back home but this is when the reality set in.

With Jenny now holding Mark's hand and John trailing behind them, Mark said, "I Ubered here, so if I can grab a ride with you that'd be great."

Jenny excitedly agreed as the three piled in Jenny's car for the short drive home. In the car Jenny explained to Mark that John has done very well in his training so far. Jenny went into far greater detail now that they had some privacy, emphasizing how John helped pick the outfit for their date tonight.

"Well I think he did a great job. You look so sexy Jenny, it's almost too bad I'll be on the floor so quick." Mark said, speaking directly to Jenny but in an almost teasing tone that was certainly meant for John.

As they arrived at Jenny's they entered through the garage and immediately Jenny commanded, "John, shoes, blouse, pants off, folded, then kneel." John wanted to hesitate at getting naked in front of another man but he was in such a state of submission that he complied without objection.

Jenny clipped a leash to John's cage and to his surprise, Jenny handed the leash to Mark. John felt a wave of humiliation pass over him but despite the embarrassment he began to leak. As Jenny went to get a glass of wine, Mark called out, "Hey Jenny, get a load of this. He's leaking as I'm holding the leash." The two laughed as Jenny returned.

Mark now bent down on one knee, extending an arm to examine John's cage. John's submission took over as he passively let another man move his panties to the side and fondle his caged cock. "Man, this thing must be tiny. I like the pink though." Mark remarked as he stood up again.

"Shall we?" Jenny said, beckoning Mark to follow. Jenny led Mark who in turn led John by leash up to Jenny's room. With Mark and Jenny fully clothed and John naked, Jenny took the leash from Mark.

Jenny led John to the lounge chair indicating that he should sit. As John sat, Jenny procured 2 previously hidden cuffs. Without resistance, she attached them to John's wrists and connected them to the anchors on the side of the chair. Jenny topped off the predicament with a ball gag fastened securely in John's mouth.

Jenny was quite proud of the sight, a sissy boy tied up in panties and a bra cuffed to a chair and gagged. As John sat in the chair he had a full view of the room. Jenny moved back to Mark and placed her hands on his rather muscular chest as she said, "Now with that taken care of, we can have some fun."

Mark leaned in, taking Jenny by the waist, planting a deep passionate kiss on her lips. John knew he should protest but couldn't help feeling like this is exactly where he belonged. In fact he enjoyed this, it felt comforting, almost like he was watching one of his favorite Blacked' videos but it was live.

As Jenny and Mark continued to kiss they slid their jackets off one another, nonchalantly discarding them. Jenny's full torso was now on display through her sheer top. John loved the view of Jenny in her heels leaning up to kiss Mark as she wore her tight, shirt skirt, knee high stockings and a very revealing top.

As Jenny and Mark continued to make out, Jenny began unbuttoning his shirt. Once Mark's shirt was off John saw just how muscular he was. Jenny again placed a hand on Mark's chest, lightly tracing her fingertips over his muscles.

Jenny couldn't take it anymore, she dropped to her knees and practically ripped Mark's pants down to his ankles. Hanging there, firm and heavy, was Mark's 10 inch cock. Jenny took a moment, grabbing toward the top and slowly moving her hand down the shaft. It was almost as thick as a beer can with a taper toward the head.

John couldn't help but stare at Mark's cock as Jenny had her hand around the base. John was also drawn to Mark's balls. Perhaps the largest pair he'd ever seen, hanging there right next to Jenny's face. "You like what you see?" Mark called over to John.

Mindlessly, John simply nodded. John loved the scene taking place before him. He loved seeing Jenny in such lust for cock, he loved her sexy outfit and surprisingly, he loved seeing the big, black cock. John let these thoughts wash over him as he was in a sort of trance by the scene as a whole.