Adventures of John and Howard 01

It was a beautiful day. John was happy his wife, Kristina, had installed a one-way film over the front windows. He was able to stand there in all the glory of Erica as he watched the neighbors going about their day oblivious to him.

Not being able to be seen from outside was a good thing for John, well to be more accurate, Erica. John was a consummate cross-dresser and loved to be dressed up as much as possible at home. Since he worked at home, he was able to be Erica even while he was working. Thanks to the pandemic and everyone working from home, people had become tired of using their cameras, so most of John's meetings didn't require him to be seen by his coworkers, leaving him free to be Erica without their knowing.

Erica smiled as she watched the neighbor, Bob, raking his lawn. Bob was about the same age but appeared older. Still, Erica was enjoying watching him work while she waited.

This was a rare occasion; Howard was coming over to visit. Like John, Howard was also a bisexual cross-dresser. Unfortunately, Howard's wife was not aware of his 'hobby', and that limited the time that Howard could spend alone with John. Most of the time, Grace wanted to go with Howard if he went anywhere; and taking her to meet John was not in the cards just yet.

Erica had diligently prepared herself for Howard's visit. Early that morning she awoke and took a long hot shower and trimmed her untamed bush for the first time in months. After which, Kristina met her in the hall and kissed her goodbye. "I changed a couple of the clothes you had laid out I think what I picked will be a better choice for today since you haven't seen each other in so long. Have a great time, and message me when Howard leaves. I'll be at the library."

Kristina had always been supportive of John's sexual orientation and his cross-dressing. She often went shopping with him to buy things for Erica. John loved her beyond belief.

Naked, Erica walked into the bedroom to see the clothes that Kristina had laid out. "Wow, well that's a different approach." Earlier, Erica had laid out a simple top and skirt, along with some everyday lingerie. John didn't own any traditional men's underwear; for years he had been wearing only women's panties, and he had quite a collection. Staring down at the bed, Erica saw a lacy red thong and matching bra, black thigh-high hose, and a tight-fitting black party dress. The accessories that Erica had laid out earlier were still there as well, her breast forms, wig, jewelry, shoes, and makeup.

Erica smiled at the changes, despite being only eight in the morning, she understood what Kristina was thinking in laying out a party dress, Howard hadn't been able to visit in a long time, and this should be a celebration.

Sitting on the edge of the bed, Erica took the lacy panties and slipped them on. The feeling was wonderful as they slid up her legs, over her ass, and embraced her cock in their soft silkiness. The Bra was next. Erica was only a part-time woman, but she was adept at putting a bra on without the twisting-it-around motion that most cross-dressers used. Before continuing with dressing, Erica slid the breast forms in place and stood in front of the mirror to adjust them. Back on the bed, she took the thigh-highs and slid them onto her legs, adjusting the seams accordingly. Kristina had chosen a pair of fine fishnet hose. The small hole pattern made them very fashionable and were some of Erica's favorites.

Erica looked at the clock and realized that Howard was due to arrive soon. She slipped the dress over her head and tugged it into place. John did not have the "perfect female body shape", in fact, he sported a beer belly. Kristina had found this dress at a second-hand shop several months ago, and she knew it was going to be perfect for Erica. Looking in the mirror, Erica knew she was right. The dress was the perfect size, with enough stretch to smooth out a few of the lumps and rolls of her manly frame. Don't get me wrong, John was not fully passable, but you had to get close to realize it.

Her phone buzzed, "I'm ten minutes out".

Quickly, she slid her red wig into place. Adjusting it, and combing it out, the look in the mirror was coming together. With her shoes on she was slightly taller than Howard, but that didn't really matter. The final touch was her lipstick. Erica didn't wear a lot of makeup, and with so little time, lipstick was going to be it for today.

John admired the woman in the mirror, the woman he had become. She was Erica, and the slight shiver that ran through her body at that moment confirmed how excited she was to be her.

Staring out the window Erica noticed Bob lift his head toward the street. A car came into view and turned into Erica's driveway. "Howard is finally here" she thought to herself, a smile bursting on her face.

Moving to the door, she prepared herself, checking her dress, boobs, and wig to ensure everything was good. The knock. Taking a deep breath and letting it out slowly, she calmed herself and opened the door. Howard stood there smiling, and Erica was entranced by the look of anticipation in his eyes. Then she noticed his look changed to bewilderment, maybe even fear. She had no idea what was going on until, snapped from her trance, she heard it too. "Hi Kristina, I wonder if you have a moment." It was Bob, and he was coming up the path towards the door.

Erica had never been fully revealed to the neighborhood, at least directly. There were many times where John, in some manner of female dress, went out to check the mail, or put of the trash, but never in the full-blown persona of Erica as he was at that moment. After a quick assessment, it was decided.

Erica let Howard pass her and enter the house as she stood holding the door open for Bob. "Hi Bob, how are you?" said Erica.

"I'm fine, Kristina, I just wanted to let you know..." his voice trailed off as he stepped up on the small porch and got a close look at the woman he was talking to. "I'm sorry I thought..." another pause, this one brought a strange quizzical look to his face. Softly he said, "John? Is that you?"

Erica retained a smile on her face and asked Bob to come in. Bob followed the woman into the house and at her request, closed the door behind himself.

"Yes, Bob, it's me John. Dressed like this, however, I prefer to be called Erica."

"Wow, I never would have guessed. I mean Jane and I have seen glimpses of you wearing strange things around the house, she thought they might be leggings, or women's gym shorts; but this." Another pause, "this is wild. I love the look, I have to say you're very pretty Erica, and that dress, my my, is gorgeous.

"Thanks Bob." Noticing him look towards Howard, she introduced them. The two men shook hands, and it was clear that Bob was confused, and it didn't help when Erica moved close to Howard and put her arm around him. She couldn't see it but assumed that Howard must have had a look of terror on his face at the thought of being outted.

"I seemed to have forgotten why I needed to talk to you."

Erica took the lead and said, "Bob, I realize that you've seen me around wearing women's clothes, and now you see me like this. I am a cross-dresser, and I like to dress like this and wear women's clothes whenever I can. I'm not really out and about in this way as I don't feel fully comfortable since I'm not very passable. I would appreciate it if you could keep this to yourself for now. Of course, I don't mind you telling Jane, but other than that."

"Oh, of course, I fully understand. But I have to say you look pretty good from where I'm standing." Bob was now taking a long slow look over Erica from top to bottom and back. "very pretty."

"Thanks Bob, but I'm just not ready for the big screen just yet." The three of them laughed.

"Does Kristina..."

"Yes, Kristina is aware of Erica, in fact, she is the one that bought me this dress."

"I love it", said Bob.

"Me too", said Howard.

Erica blushed a bit, but continued, "Bob, Howard is... well... my boyfriend, if you know what I mean. Kristina knows about him too and she's cool about it. It's just that his wife doesn't know."

Bob's face seemed to light up at that comment and said, "Oh, I understand, I can be very discrete." He looked from Erica to Howard and back, "I guess I'm interrupting something. I'll go."

His face seemed to take on a dejected look. Erica caught the change and said, "You don't need to leave." Turning to glance quickly at Howard she then turned back to bob and said, "You can stay a while and have coffee with us."

Bob's face began to glow, and he said, "I would like that."

They all seemed to be happy, and the two men followed Erica into the living room. "Bob, why don't you have a seat, and we'll be right back. I'd really like for you to meet Michelle." Erica picked up a magazine from the side table and handed it to Bob. "We might be a few minutes, but definitely wait for us.

"Ah, sure." Bob was confused, he didn't realize there was someone else in the house, but still he sat and watched as the two went into the bedroom down the hall. They closed the door behind them so he couldn't see anything, but if he listened closely he could hear them talking. His mind raced with what they could be doing, and who Michelle could possibly be. He flipped the pages of the magazine, but his curiosity was focused on what was going on behind the door. He quietly walked closer and tried to hear them.

Erica was saying, "Take everything off, and let's get you dressed."

"I love the outfit that you've laid out for me today." Bob heard Howard saying. There was more conversation, but it was very confusing to Bob, and not wanting to get caught, he returned to the chair and unsuccessfully tried to read the magazine.

Inside the bedroom, Howard was now naked and bending over the bed while Erica slid a lubed butt plug into Howard's ass. Howard stood up slowly, adjusting to the intrusion. Erica handed him a pair of pink panties and a matching pink bra. They weren't lacy like her own, but they would suffice for today. After putting them on, Howard started to put on a pair of black pantyhose. He wasn't as good at putting them on as Erica was, but that was only due to the limited practice he had. Erica knelt and assisted him in getting the legs bunched up so he wouldn't tear them when he pulled them up. She didn't mind if they were torn, but with the possibility of Bob seeing them, she didn't want Howard to be embarrassed. Erica knew full well she had chosen this pair especially to be ripped open later in the date when it came time to replace the butt plug with something more personal. As Howard stood to finally pull the pantyhose up, Erica couldn't resist the opportunity to plant a kiss on the panty covered bulge that was now staring her in the face. Had Bob not been waiting for them, Erica would probably have started getting busy right then and there. She managed to restrain herself and let Howard finish his transformation into Michelle.

Michelle usually didn't wear makeup, even lipstick, so with her dress, wig, and shoes on, she was ready to go. The pair kissed once more before heading back into the living room and Bob.

"Bob, I'd like to introduce Michelle." Bob stood up and was surprised when Erica moved to the side to reveal that Michelle was Howard dressed as a woman too.

"Wow, you're a cross-dresser too?" he asked.

Michelle replied, "Yes, and I'm definitely not passable". The group laughed as Michelle ran her hands through her beard.

Michelle sat on the sofa, and Bob on the recliner as Erica went to get coffee for them.

Erica listened to the conversation between the other two and noticed that it was not forced, in fact, the pair seemed to be comfortable with each other. This made her happy as she feared things might be awkward.

Returning with a tray of coffee and snacks, she set it down and sat next to Michelle, but close to Bob. "We like to get together and have a women's day out, without actually going out."

"Well, thank you for inviting me to join, I think this is awesome."

They talked for a while about a lot of different things, and then during a lull, Bob asked softly, "Is there more? I mean, am I overstaying my welcome, do you two want to be alone?"

"Well, to be honest Bob, Michelle and I will be getting it on as it were, but I wonder if maybe you want to stay and join us?" asked Erica.

"Join you? I'm not..."

"Oh, Bob, we're just two women that are eager to please you. Just think of it that way. We're not suggesting that you need to do anything you're not comfortable with."

Bob didn't reply but watched as Erica turned to Michelle and the two women embraced and kissed passionately.

After a long kiss, Erica moved over to Bob, and held out her hand. He took it and stood up. With her arms around him, Erica looked into his eyes and said, "Will you kiss me?"

Bob was hesitant, but Erica didn't force it; she waited for him. She thought he would struggle with the idea a bit, if not outright say 'no', but instead, he moved his face closer to hers and their lips met. It wasn't as long or passionate as that shared with Michelle, but it still brought a smile to Erica's face.

"I didn't expect to like that as much as I do." Said Bob. Erica smiled and with her fluttering eyelids and a slight nod of her head, invited him back into another kiss. This one was longer, and Bob even allowed Erica's tongue to slide through his lips briefly. Erica stepped back and reached out to Michelle. The other woman rose and moved in to take Erica's place with Bob. Bob was a bit more hesitant this time but still kissed Michelle. When their kiss broke Bob giggled, "the beard tickles." The others joined in with his laughter.

"Sit and watch." Erica instructed Bob, who, reluctantly, broke the embrace with Michelle and sat down to watch. Erica sat on the sofa and without any prompting, Michelle dropped to her knees between Erica's legs and lifted the woman's dress to reveal her pink panties, which were lacy and see-through enough for Bob to clearly make out the cock they were embracing. Erica noticed Bob as he eagerly watched as Michelle deftly released Erica's cock through the leg hole of her panties before licking the shaft base to tip.

Bob cooed as he watched Michelle take Erica's cock into her mouth, sliding her lips up and down the shaft. His hand moved to his own crotch and began to caress his stiffening member through his pants.

"You can take that out if you want." Said Erica to Bob. A moan of approval came from the cock-stuffed mouth of Michelle as well.

"Really, should I?" asked Bob, but he didn't wait for an answer, he stood up and started unbuttoning his pants. When he dropped them, Michelle stopped to watch as Bob removed his boxers to reveal his hard cut cock.

Sitting back down, he began to stroke it as Michelle resumed her sucking of Erica's cock.

Erica saw the hunger growing on Bob's face as he watched Michelle service her cock. She touched Michelle's shoulder and her head tilted up to look Erica in the eyes. Erica's gaze darted from Michelle to Bob and back a couple times, and Michelle got the message. Releasing Erica's cock from her lips and giving it one final kiss on the tip, she slid herself over towards Bob. A surprised and eager look came over the man's face as Michelle, still on her knees, slid between the man's legs and took hold of his raging member. Erica wasn't sure he wouldn't explode right then and there. Certainly, thinking the same thing, Michelle didn't spend too much time massaging and licking Bob's cock before sliding her lips onto it and engulfing it into her mouth. It was a good thing too, for it was just a few moments later when Bob's head rolled back, and a loud moan accompanied the eruption of his hot cum into Michelle's waiting mouth. Michelle took some of the load in her mouth and then pulled back taking the rest of his cum on her face.

Taking him back into her mouth when his spurts subsided, she sucked the remnants from his cock. Bob looked down at her and said, "That was wonderful." Michelle sat back on her haunches, cum in her beard and dripping from her chin, her mouth open showing Bob his cum. Without prompting, she slid back over to Erica and rose enough for their lips to meet. They kissed sharing Bob's cum, who was amazed by this action and called out, "fucking amazing".

Erica licked the cum from Michelle's face and beard before saying, "Michelle, I think some of Bob's cum is on the floor". Michelle turned and lowered her face to the hardwood floor and began to lick the spilled droplets of cum.

Erica turned to Bob and asked, "I'm going to fuck her now, would you like to watch or join me?" Erica knew Bob was not going to leave but she didn't want to assume his further involvement. Bob replied, without much hesitation, "I'd like to watch", Erica understood this might be difficult for Bob to process, he had already stated he wasn't gay, but after a short pause the man added, "at least until I have recovered." A huge smile covered Erica's face; she couldn't tell how Michelle felt about that development as she was still on her hands and knees licking cum from the floor, but knowing that Michelle was fully submissive to Erica, it would only be a matter of instructing her and soon Bob's cock would replace her own in Michelle's boi-pussy.

Taking advantage of the opportunity with Michelle already in the doggy position on the floor. Erica moved down and knelt behind her. She lifted the hem of Michelle's dress up. Taking hold of the pantyhose, Erica pulled the seam apart to make a hole to access Michelle's ass.

Bob watched as Erica reached over to the side table and picked up a small package. He wasn't too surprised to see Erica opening a condom and sliding it onto cock that was still poking out of her panties. He was surprised though when he saw Erica slid the large black butt plug out of Michelle's ass. Without hesitating, Erica tossed the plug aside and slid her cock into the gaping hole it had left in Michelle's behind. Michelle moaned loudly as the long rigid member slid down into him.

It wasn't long before Bob was becoming hard again watching Erica slide her cock in and out of Michelle's ass. An eagerness grew within him knowing that Erica had said he could join.

Erica was not oblivious to Bob's growing excitement and asked the man to stand up in front of her. With her cock buried in Michelle's boi-pussy, Erica took Bob's cock into her mouth and suckled it to full glory again. Bob was moaning loudly and thought for sure he would explode soon if she didn't stop tickling his shaft with her tongue. But before he got too far, Erica let Bob's cock fall from her mouth as she reached to the table and took another condom. This one she carefully slid onto Bob's shaft. "Are you ready?" she asked the man, who could only nod his response.

With her instruction, Bob knelt next to her and watched Erica slide herself deeply in and out a few more times before pulling out completely. She then moved out of the way, returning to a seat on the sofa to watch. Bob didn't need any prompting, and moved into position, guiding his cock into Michelle's well-used boi-pussy. Michelle moaned as the man said, "this is the first time I've done anal, the feeling is so different." He continued to fuck Michelle slowly at first and then faster as he built to a good rhythm.

It wasn't long before Bob was moaning again as well, as he held himself deep in Michelle's ass. When he finally collapsed back onto the floor, Erica saw the cum filled condom hanging from his still semi-hard cock. Michelle had dropped onto her side revealing a small puddle of cum in her panties.

After a while, Erica suggested they three of them get washed up. Bob announced that he needed to get home before his wife came looking for him and asked to use the bathroom first. The others agreed. While Michelle was taking her turn, Erica was saying goodbye to Bob. "I'd like to do this again." The man said. "You're welcome to come over and play with me anytime. It's a little hard to get Michelle here, but I'm sure the two of us can entertain each other quite well on our own." Erica replied and then leaned in for a final kiss before Bob opened the door and let himself out.