Howard is Ours Ch. 02

Howard was excited. Peeking out the front window, holding the curtains to cover the fact he was wearing a dress, he watched as his friend, and bi lover, drove away with his wife. Something fantastic had just happened to him, and he couldn't wait to see where it would lead.

Howard had been a closet cross-dresser and even more closeted bi-sexual for a long time. He had met John several years ago, and since then the two had become friends as well as play-partners and lovers. While it had been difficult to arrange playdates, Howard giggled with glee that all that would change given recent events.

Earlier in the day John came to visit. This was not their usual playdate where they would both get dressed in their feminine attire and enjoy a few hours of sexual enjoyment. This time it was just a casual get together to have a beer and chat. The chat, though, revolved mostly around when they could plan another getaway. This had been interrupted by Grace, Howard's wife, who had returned home early.

Well, much to Howard's immediate dismay, Grace announced that she was fully aware of the affair the two men were having, and their predilection towards wearing women's clothes in the process. What was an even bigger surprise to Howard was the fact that she condoned the behavior and was happy that he had someone to share his desires with.

It was no secret to Howard that he was not able to satisfy his wife sexually, and as a result, they didn't have sex to any great extent. Howard received his relief with John and learned that Grace was seeing her girlfriend for her relief.

Well, as much of a roller coaster of emotions Howard went through in that revelation, he was further surprised that Grace wanted to be fucked by John, which the pair did while Howard watched from a chair wearing lingerie supplied by his wife.

Howard thought, "Phew, this has been an incredible day", as he turned from the window, the car gone from his sight.

Grace and John were on their way to John's house so Grace could meet John's wife, Kristina.

Howard was acutely aware that his wife and John would be having sex again when they returned to John's house. He was also certain that John's wife, Kristina, would be participating in that very same adventure. Funny enough, this knowledge didn't bother him as much as one would think. He knew that not only was his secret life and lover revealed to his wife, but she had also fully accepted it. She had even commented on knowing about him for a long time and was just waiting for the right opportunity to discuss it. This made him feel extremely happy and relieved. He was finally going to be able to live the fantasies he so cherished.

There was just one thing; they had left him alone at home with certain expectations. Alone while they were off having fun sparked a small resentment. He had enjoyed the part of being forced to watch, and to clean up afterwards. He enjoyed them peeing on him in the bath. He wanted more of that, and while he logically knew that would happen, he was still alone.

His hands roamed over the silky dress Grace told him to wear, and it felt luxurious. Brushing over his crotch, he felt the wetness of his panties, the stickiness of his cum and John's saliva from the blowjob John gave him before they left. He realized that John wasn't going to leave him by the wayside. John was as shocked as Howard at Grace's revelation, and he just needed time to think. Howard brought himself out of the small worry-fest that had taken hold.

Deep down Howard had a submissive personality and enjoyed it when John ordered him around during their playdates. John took on the personal of Mistress Erica, the dominant role in their relationship, and Howard thoroughly enjoyed every minute. Howard realized this is just another order from Mistress Erica; he might not understand it all yet, but he will.

Howard went to sit in his favorite recliner. The feeling of the silky dress on his thighs made him shiver with delight. He was happy. After years of keeping his crossdressing and bisexuality hidden from his wife, she now knew and accepted everything, even some of the kinkier activities that he liked to partake in. She had even loaned him the lingerie and dress he was currently wearing.

He marveled at his luck; not only was he able to share clothes with his lover, John, but his wife's clothes also fit him quite well. This was, of course, something that he already knew of his wife's sizes, but he had always steered clear of trying her clothes on for fear of getting caught.

Relaxing and thinking about the tasks they left him to do, his mind drifted back to the day when he first met John, several years earlier.

Howard was nervous, more so than he had been in years. He had just pulled into the hotel parking lot and was about to head up to a room where another man was waiting to meet him. The two had chatted for a few weeks online and set up this meeting after deciding they shared a common interest and wanted to take it to the next level and meet in person. That common interest revolved around their mutual interest in dressing in women's clothes, and a desire to sexually experiment with another man.

His name was John, and from the pictures, was good looking enough, and while not passable as a woman, still looked good when dressed up. John was further along in the cross-dressing world than Howard; he had accessories like a wig and breast forms that Howard had not been able to safely acquire. Howard had already had a close encounter when his wife stumbled across his hidden bag of clothes in the garage. He had been able to claim they belonged to his ex-wife, but Grace made him discard of the bag of clothes.

Over time, Howard had built up a new, smaller stash from short visits to thrift and second-hand stores; this time finding a better hiding spot that was less likely to attract attention. His meagre stash was now inside the knapsack he was carrying.

He slowly walked into the hotel. Glancing around he had the distinct thought that anyone he made eye-contact with would immediately know why he was there and judge him for it. At the time, he didn't realize that no one gave him a second look.

The elevator door closed leaving him alone in the small compartment; he let out a sigh of relief as he double checked the room number on his phone. A few minutes later he found himself standing in front of the door. What Howard didn't know was John had been anxiously waiting for him and had been pacing the room for the past fifteen minutes, checking the peephole each time he passed the door. John was now staring at the man and debated opening the door before he could knock.

The pair seemed to act at the same time; John pulled the door open as Howard's knuckles touched it for the first time.

Howard looked upon the woman that stood before him and was briefly confused. He hadn't expected a woman to answer the door, but then as his eyes focused on her face, he realized it was John all dressed up. The door closed behind Howard as the two moved into the room. The bang of the door startled them, but after the brief jump scare, they both broke out laughing, their anxiety lessening.

The two men introduced themselves and talked for a short time. The room had only an office chair and a side chair for them to sit on other than the bed. Howard took the side chair and John sat at the desk. Howard had already known that John, when dressed, preferred to be called Erica, and was doing so. Soon the pair had relaxed, and Erica said, "I would love to meet Michelle."

"Oh, yea, sure." Howard seemed to get a bit flustered again. Nervously he said, "I don't have a lot of clothes with me, in fact, I don't have a lot of clothes at all."

"No worries, I can see that we are similar in size, and you are welcome to whatever you want to try from my bag." Erica pointed to a small suitcase, open on a stand near the bathroom.

"I have some lingerie, but I wouldn't mind trying a dress if you have one. I really don't get to dress up very often, and certainly not for very long."

Erica was pleased to see that after taking a dress from the suitcase, Howard lay it on the bed and began to undress in front of her. She had been wondering if Howard would have preferred to go into the bathroom and return as Michelle. As exciting it would be to see the finished product all at once, watching the transformation was equally exciting. Howard didn't hesitate to get completely naked before pulling a pair of pink bikini panties and a matching bra from his bag.

With his feet in place, he slowly slid the panties up his legs and stopped when Erica moved to sit on the bed in front of him. Watching the woman, Howard saw her eyes were fixed on his now hard cock. She reached up and touched it, briefly caressing him. Howard worried things might prematurely explode and was about to say something when Erica let him go. She cooed and said, "I love it; but I want to see you dressed." He continued to pull the panties up and moved to the bra and dress. He fumbled a bit with the bra and mumbled "I don't get much practice putting it on." Then he added, "or taking one off for that matter." The pair laughed. Erica commented, "It's not a problem baby, we're here to have fun and enjoy each other".

Erica stood in front of the now fully dressed Michelle. "Very Pretty" she offered, "I'm pleased to meet you, Michelle."

Howard felt relieved that despite not having breast forms, or a wig, or shoes, or anything else, Erica still accepted him as Michelle. When her hand touched Howard's shoulder, the pair drew together into their first kiss.

Uncertainty seemed to wash away as their hands began to explore and caress each other.

With brief pauses for air, they kissed for a very long time.

Michelle made the next move and slid her hand between them to embrace Erica's hard cock through her dress. Michelle knew the move was welcomed when she felt Erica's tongue probing at her lips.

Eventually they collapsed on the bed, and Erica said, "I want to taste you." To which Michelle replied with the same words. Squirming about, the pair moved into a 69 position. Each lifting the other's dress. Erica quickly had Michelle's cock out through the side of her panties, but it seemed that Michelle was having a bit of difficulty as Erica was wearing pantyhose.

Reaching down, Erica took hold of her own hose, and ripped them open at the crotch. Then, she slid her cock out of the leg opening as she had done with Michelle. "Wow" was all that Michelle said before taking the other woman's cock into her mouth.

While it wasn't the first cock that either of them had sucked, they were no where near experienced. That mutual state of inexperience seemed to make the moment even more powerful for them.

With the excitement, anticipation, and fear, of this moment, neither woman lasted long. Michelle was the first to explode, but Erica wasn't far behind. Howard recalled wondering what he should do at that moment, but when he realized that Erica had swallowed, he did the same.

Sadly, the aftereffects of guilt invaded each of them quickly after ejaculating; they seemed to struggle over each other to get up and get back into their male personas.

By the time they were redressed and ready to leave, John said, "I want to do this again." Howard agreed. They hesitantly moved in and kissed again, not the same passionate kiss as before, but a kiss, nonetheless. Barely more than an hour had passed since he arrived when Howard found himself back in his car and ready to go home. John had stayed behind; he had a lot more to pack up, and the pair thought it best not to depart together.

Over the years, Howard and John managed to get together more frequently and enjoyed much of the same pleasures with the guilt lessening each time. Howard loved the dynamic that was growing between them and looked for ways to try and meet more often.

He snapped back to the preset when his phone chimed, announcing a new message. It was from John. For years they had been hiding their conversations in emails, apparently not as well as they thought they were. Now, John had openly texted him with, "Michelle, prepare yourself and come over to my place as soon as possible."

Without hesitation, and a lot of exuberance, Howard responded, "Yes Mistress".

He jumped from the chair and raced to the garage to get retrieve his hidden clothes and toys. He had to prepare himself, and then gather everything as he was instructed earlier before driving over to John's place.

Running on autopilot, his mind drifted back to that special day. Excitedly, he stood in yet another hotel room, this time wearing a red dress over a matching set of black bra and panties with black thigh-highs. John had supplied all of the clothes Howard was wearing and even brought an extra pair of inserts which felt strange against his skin for the first time. He was also wearing high-heeled shoes that made him wobble a bit, making it hard for Erica who was applying lipstick to his lips.

The excitement wasn't just from the fact that he was fully dressed, there was more to come, and it was something he had wanted for a very long time.

"Michelle", said Erica as she put the lipstick down on the counter, "you are dressed but are you ready?"

"Yes." She said with a tremble that came from excitement or fear, she really didn't know which.

"Then let's start.", Erica took control of the situation and with the two women facing each other, she began.

"Michelle, why are you here today?"

"I offer myself to you, Mistress Erica, and ask that you take me as your submissive."

"Knowing what it means to be a submissive, is this what you honestly want?"

"It is, Mistress."

"Kneel Michelle." Placing her hands on the kneeling woman's head, Erica continued, "please respond accordingly. Do you Michelle freely offer yourself to be my submissive?"

"I freely offer myself as your submissive."

"Will you accept, respect, and follow, my commands?"

"I will accept, respect, and follow, your commands."

"Do you freely give your body to my service?"

"I freely give my body to your service."

"I accept you, Michelle, as my submissive. Now stand."

Howard, as Michelle, stood in front of Mistress Erica smiling. Mistress took a cup from the counter and handed it to him, saying, "Michelle, take and drink of my essence".

Michelle took the cup and drank the contents without hesitation, knowing full well that the cup contained a cocktail of Mistress Erica's cum and pee. Michelle finished the cup before handing it back.

"Welcome Baby Girl. Now let's move to the next step."

Michelle knew everything that was going to happen to her that day. They had exchanged many emails and Erica was happy to share the details. The last thing Erica wanted was for the day to go bust because they started something they weren't comfortable with.

Erica sat on the bed, and Howard knew exactly what to do. Walking over to the bed, Michelle lay face down over Erica's lap. There was no pause or preamble, the moment Michelle was over Erica's knee, the first smack came down upon her ass. The second wasn't far behind, and after the third, Erica lifted Michelle's dress and planted two more slaps on her panty-covered ass.

Satisfied with her work, Erica said, "Have you prepared yourself?"

"Yes Mistress, I have, just as you told me to." Said Michelle, still bent over Erica's legs. Rubbing her hand over Michelle's ass and slid the panties to the side. She picked up a lubed butt plug from the nightstand and rubbed it over Michelle's hole; slowly working it into place. When it was fully inserted, she pulled the panties back over and told her to stand up.

They stood and embraced, kissing her passionately. Michelle was wobbly from the spanking and getting accustomed to moving about with a butt plug inserted.

Helping her over to the table and chairs, they sat down, which Michelle did slowly. Erica suggested they take a short break and let the plug do its job.

The pair drank the coffee they had brought with them, and talked a bit about what was going to be expected of Michelle as a submissive.

"I'll take this opportunity to remind you that as my submissive, I expect you to greet me whenever we are together by kneeling and kissing my crotch. It doesn't matter if you or I are dressed at the time. You will then strip, and if you are not wearing any lingerie, put some on before returning to a kneeling position and taking my cock into your mouth."

"Yes Mistress, I understand" said Michelle happily.

Over the course of the next twenty minutes or so, they talked about how Erica would happily accept any deliveries on behalf of Michelle. It had become easy for the pair to purchase women's clothes online, but with Howard's wife scrutinizing anything that came, Michelle would direct the shipment to Erica's place where she would receive and store them. John was still in a somewhat confined relationship as well, but his wife knew about his cross-dressing even though she didn't like it.

When Erica finally stood up, Michelle knew it was time and stood as well. The pair went over to the bed where Erica pulled out her cock and put on a condom while Michelle watched. At Erica's direction, Michelle turned and leaned over the bed. Erica took out the plug and lubed herself and Michele's hole. Lining herself up, she placed the tip of her cock against Michelle's rosebud and said, "Michelle, I now take you as mine." Slowly, but deliberately, Erica slid herself into the other woman's ass. Michelle, who had never been fucked by anyone before, squirmed a bit and moaned as the large cock entered her. She recalled being happy that Erica hadn't driven herself home in one hard fast movement. To the contrary, Erica was slow and gentle, and even stayed buried inside her for a while, unmoving, so Michelle could get accustomed to having a cock inside her ass.

Snapping back to the present; Howard knew the implied meaning of "getting prepared" and had completed the ritual of cleaning his bowels as part of his 'preparation'. He then took a quick shower, knowing that very soon he was going to be fucked again my Erica.

Before getting dressed in the same lingerie once more, he took his medium butt plug and some lube and inserted into his ass. He would wear the plug on the drive over and was certain that by the time he arrived, he would be open enough to receive Erica without wasting any time.

With the lingerie on, he pulled on his man-clothes over top. Michelle's clothes and toys were in a bag and ready to go. He even threw in the dress he had been wearing.

He thought for a moment about the other commands they left him with, especially cleaning out his closet and drawers of man-clothes and underwear he wouldn't need anymore. The timing of Mistress' message would not have allowed him time to do them anyway, and he hoped that Mistress would understand; but, he was prepared to get a spanking just in case. With a smile growing over his face, he locked up the house and knew that they likely wouldn't be back till the next evening.

He wasn't accustomed to driving while wearing a butt plug, but he managed to get there safely in a little more than the average 20 minutes. He stood at the door shivering with excitement. He didn't know what he was going to find on the other side, but one thing he knew for sure, he wasn't being left out; even if all they wanted was for him to watch. Though deep down he believed the comments about "you're just going to get to watch, if your involved at all" were just hype.

He rang the bell. He could hear music playing inside, something soft, he knew it, but couldn't place it right off.

The door opened, and Erica, fully dressed and accessorized, stood there with a huge smile on her face. "Come in Michelle." She stepped back to let Howard enter the house.