She was starting to get bored with her life and was searching for something more. About a year ago, Brian dropped a bombshell on her. He had been secretly dressing up in women's clothing behind her back. He had been dressing up since he was a kid, but he stopped when the two of them got married. He started again not long after Monica became a home maker.
Monica had the talk with him about what it all meant. He said it was a turn on to him to wear lingerie. He also said he often wondered what it was like to be a woman and had started playing with toys. He showed her his lingerie collection, which included some sexier things than she had. She had to process all of this, and at first she felt betrayed by him and considered leaving him. But, she knew he loved her. She loved him too.
Monica was an attractive woman. She had black hair and hazel eyes. She was always getting her hair and nails done. She did keep herself in shape with exercises and walking the treadmill they had at home. Though she had nice breasts, she would probably say her best feature was her shapely ass. She prided herself in keeping it in shape. Monica was also a writer and wrote the first romance novels the company published.
She read up on the whole sissy culture to try to understand her husband. She had already found that he was letting her make many of the decisions at home and suspected he had a strong submissive side. However, she wasn't really the hard core Domme type. She saw herself as more of a sensual Domme who liked to use tease and denial to get him to comply. Two things changed from that point on.
First of all, she began dressing her husband, which meant whatever lingerie she picked out for him would be worn underneath his clothes when he left home. It was usually frilly panties and a camisole. Sometimes a sports bra or an even sexier bra. She sprayed him with perfume and disallowed cologne. She had his toe nails painted and his body shaved. Occasionally, she ordered him to wear things that had him on edge all day, fearing that he would be caught, but he always did what he was asked to do.
In the bedroom, he wasn't performing sexually the way he had. Brian wasn't particularly well endowed, but he had been adequate before these revelations. He improved greatly in the oral department, but he wasn't really getting it done otherwise. He tried, and it caused him anxiety when he failed. Her teasing probably didn't help as she was calling him Brenda, her lesbian lover and joking that she needed to find a real man to satisfy her. Privately, she wondered if he might really have gender identity issues, but they hadn't had that discussion.
She was conflicted. She really wanted a lover who could satisfy her sexually, but it felt like cheating on Brian if she did it. Brian never told her not to seek a lover when she teased him. He just got quiet. She thought about this every day, but the solution eventually presented itself. It was not something she expected, but when it happened, she was hooked.
Brian needed a new secretary to help keep him organized and focused. Edna had been with him since he opened the business, but the older woman decided to retire. That's when Stacy entered the picture. She was a knock out. Beautiful blond hair and blue eyes. She had the most shapely round ass, and Brian was a man who enjoyed looking at a beautiful woman's ass. Her breasts filled out her bras nicely. Stacy dressed provocatively, but when she smiled, he was putty in her hands. The only other woman who had that effect on him was his wife.
When Stacy entered his office for the interview, she was the 12th person he had seen. None of them sounded right, and she certainly sent off warning lights in his head that day. Any pervert of a boss would have hired her to play with, but he needed somebody who could handle anything. She would be practically running part of the business, or basically executing parts of his agenda for him while he was working on negotiating a buyout of a rival company.
For some reason, Stacy chose a tight red dress that barely contained her breasts, and she wore the prettiest shade of red lipstick. He found it difficult to look at her resume when she was staring at him with those adorable blue eyes. "So, um, " he nervously cleared his throat. "It says here that you have no college education, no experience as a secretary and..." He looked at her. "I'm sorry, but why should I hire you? You do realize this job will be demanding?"
"I can type really well, " she smiled, and he found himself tenting in the pink panties his wife had dressed him in under his suit.
"I see, but..."
"Mr. Griffin, I can do this, " she interrupted. "I can do this. I know you need somebody who has managerial skills. I practically ran my home for my mother and raised my four brothers and sisters with her. I'm creative and can think under pressure. I can even write..."
He shook his head. "Still, I don't think I can hire you, " he looked at her and noticed a tear in her eye. "It's just that you..."
"Please, just give me a chance, " she pleaded desperately. "I need this. I need the money, and I know I'll do good if you give me a chance. Just give me a week. If I'm not good, you can fire me."
He looked at her resume again, knowing that nothing on it suggested that she was right for this job. However, her tears and her beautiful face overrode logic. He smiled. "Okay, I'll give you a chance. Be here tomorrow at 6 a.m. Edna will be here to show you what she's been doing. That will be a start, but I'm telling you there will be more than that."
Stacy turned out to be a big surprise. She showed up at 5:30, waiting for Edna. Again, she dressed provocatively, but her attitude towards work was professional. When Brian arrived, she brought him coffee and a doughnut and breezed through the documents she was expected to type. Brian put her on the new erotica department that the company was establishing. She surprised him by coming up with a better plan for marketing the books.
Brian wouldn't have believed it, but Stacy was perfect for the company. At the end of the week, he informed her that she was hired full time. She smiled. "That's great sweetie, but I'm gonna need another $2.00 an hour for this, maybe more."
Sweetie? $2.00? Who does she think she is? He looked at her and those blue eyes got to him again. "Okay, we'll do it, but don't think this is gonna be easy, Stacy. It's just the beginning."
She shook his hand. "I hope so. I'm always up for a challenge."
Things seemed to be going better for Brian and Monica at home, but Brian was always praising the new secretary. She's amazing. She did this and that. She saved us money. The erotica department is taking off. Monica began to wonder if there was something going on between the two. But, Brian was every bit as attentive to Monica's needs as ever.
Monica walked into the room in a red robe as Brian sat on the bed. "So, are you fucking her, " she asked?
"Sweetie, you know you're the only woman for me, " he replied.
She shook her head. "That's not an answer, dear. Are you fucking her?"
"No, I'm not fucking her."
She stood in front of him, smiling seductively. "But, you want to fuck her, don't you?"
Was she jealous of his secretary, playing a game or both? "Sweetie. No, I only want you."
She giggled. "Oh, who am I kidding. That little thing can't satisfy me. She'd probably laugh you out of the room once you pulled down your panties." She looked him in the eyes. "Does she know you wear panties every day under your fancy suits?"
He went read in embarrassment. "No. Of course not."
She walked to the door and turned around. "Maybe somebody should tell her that her boss is really just a panty wearing sissy."
He stood up. "Sweetie, you aren't seriously thinking about telling her, are you?"
"Well, I don't know, " she replied with an evil grin. "We do have the office party on Friday, and I think it's time I finally met this woman."
Brian was hoping she was just teasing him again as he approached her with a hug. "You know I love you. You're the only woman I want to be with in any way. " He felt something poke him as he hugged her. "What the.."
"I see you felt my surprise for you, " she laughed as she disrobed to reveal her red lingerie set and a modest six-inch strap on cock. "Do you like it?"
He backed up. "Sweetie, a strap on? I don't think I can handle that."
She stepped up to him and took his hand. "Nonsense. You can handle it. Besides, I'll be gentle." She gave him the look that always made him melt, "You did say you wanted to be with me in any way, right?"
"But I..."
She squeezed his hand. "I want you in this way, baby. I want to fuck you like a woman." She laughed. "I want to make you my bitch. I think it's time, don't you?"
The tent in is baby blue panties revealed how turned on he was. "Baby, I don't..."
She reached over to the dresser for a tube of red lipstick and handed it to him. "Here sweetie. Put this on."
"Why?"
She flashed her hazel eyes with an innocent look. "To suck my cock so you can get it ready for that tight little ass of yours, silly."
He started putting the lipstick on, but she stopped him. "Do it like I taught you, Brenda."
"My name is Brian, " he protested as he turned to the mirror to carefully apply the lipstick as he had been taught.
She shook her head. "You have to be Brenda, sweetie. A real man wouldn't wear panties and make his lips all pretty to suck my cock." She looked at his lips. "Oh, that's just just perfect. Now, smear that lipstick all over my cock. Show it some love."
He tentatively got on his knees in front of her and kissed her cock, leaving a nice lip print. "Aren't you the one who used to talk about lipstick on your cock, " she teased? "Well that's a good start. Show me how it's done."
She had never done this with him until now. His sucking adventures had been in private with his own dildo, and he was turned on by this turn of events. The fact that Monica seemed really into it made it better. "I knew you were a cock sucker. Look at that lipstick all over my cock, and pretty far down too. You are a little slut, aren't you Brenda?"
He looked up at her. "I love you."
"I know you do, " she replied with a laugh. "We'll see how much you love me when I have this deep in your ass. I guess now you'll be expecting my cock, won't you? Begging for it?"
He barely took his mouth off of it to answer. She knew she had him where she wanted him. "You'll have to make me happy and earn that honor first, but I do want you ready. You never know when I might have you serving a real cock, since yours is so inadequate. I've been so good to you, but maybe I should lock it up."
"Another cock, " he wondered to himself. Was she seeing a guy? He didn't like the thought of being locked up. "Please, no chastity."
"You don't get a vote in that, " she replied. He seemed to be getting into sucking her cock, and she privately wondered what it would be like to see him suck a real cock for her. She could see him gagging as he tried to take it deep. "Okay, that's enough foreplay, princess. On your hands and knees at the end of the bed. You know what's coming next."
He nervously took his position on his hands and knees and looked back at her. "Sweetie, I don't know if I can do this."
She rubbed her hands on his ass and teasingly poked at it with her fake cock. "Nonsense. You've had dildos in your ass before, or did you forget you mentioned that to me before?"
"But that was different."
She pouted as she grabbed some lube and began probing his tight hole with her fingers. "Don't you trust me, Brenda? I thought you trusted me."
"I do trust you, " he replied.
She was pushing her cock head against his tight opening. "And I trust you. I know you have been faithful to me. Not that your secretary would have use for your little wee wee anyway. Plus, you'd tell me first, wouldn't you."
"I would never be with another... Aww, God, " he yelled as she pushed into his ass and it gave way.
"Shhh, don't yell. It will wake up the kids," she giggled. "Want them to see me fucking you in the ass?"
He grabbed a pillow and yelled into it as he was still feeling discomfort. Her rubber impaler was easing into his well lubed hole, but it still hurt. He hadn't played with his toys since telling her the truth. Secretly, this is what he was hoping for, but he didn't want to push her. He wanted her to embrace this, and he felt lucky that she seemed to be opening up to it.
She felt empowered as her husband screamed into a pillow with her plowing his ass. She wasn't sure how she would like this, but it was turning her on reversing the roles in the bedroom. "Good girl. Just relax. You'll get used to it. Isn't that what you told me when I let you have my ass the first time?"
It was starting to feel better as he looked behind at her with tears in his eyes. "I love you, Monica. You are my Goddess."
She shoved it in deep and he groaned in pain. "Your Goddess demands access to every inch of your body for her pleasure. Can you handle that?"
He was pushing back to take the cock deep. "Yes, my Goddess."
"Even if it means I'm the only one allowed to cum?"
He whimpered. "Yes. I belong to you."
"Good girl, " she replied as she held it in deep. "And for the record, I will let you know when I decide I need a big cock."
He looked back at her with a hint of sadness in his eyes, and she knew what that was all about. "Oh, for crying out loud, I'll let you watch."
She grabbed his hips and began thrusting in and out at a steady pace. "You certainly are sensitive little bitch, aren't you? It turns you on at the thought of watching a big cock fuck me hard, doesn't it?"
"I just want you to be happy, " he moaned as he was really getting into the pounding he was taking.
Monica was quite aroused herself as she continued to deflower her husband with her newly purchased cock. "You'd suck his cock for me, wouldn't you?" He said nothing. "You'd let him fuck you if I ordered you to, wouldn't you?"
He said nothing, but the way he was riding her cock told the story. She started to finger her wetness and noticed him staring to stroke his cock. "Oh no. You don't cum until I tell you you can."
She pulled out of him and removed the strap on as she took a position on her back in bed. "Eat me baby. Right now. Put your tongue in my pussy."
He didn't have to be ordered to do that. Many times, he begged for it. He worshipped her pussy. He knew all the right places to drive her wild, and it gave him confidence knowing nobody could make her feel this way with their oral skills but him. Plus, he craved her taste. This was the woman he wanted to spend the rest of his life with.
It was in these moments that her honesty came out. He could make her feel like nobody else could, and she couldn't imagine herself with another man, even one with a big cock. "Right there, baby. Yeah, oh yeah. God, right there baby. I'm gonna cum, yeah. Oh God. Baby, I love you."
She had just enjoyed a big orgasm when she allowed him on top of her to cum inside of her wet pussy. He knew he couldn't last long, but he kissed her passionately as he released his seed inside of her. As frequently occurred in this situation, she had him clean her pussy once again. Moments like this made him feel like the luckiest man alive.
She kissed him. "Sweetie, that was wonderful. Could you go get me a drink?"
He reached for his pink babydoll nightie and panties. Most nights, she selected the lingerie he would wear to bed, and this night was no different. He went to the kitchen for a drink. He returned to find her asleep, so he put the drink on the nightstand, crawled into bed beside her and drifted off to sleep.
Monica may have talked about having other men, but she really wasn't serious about it. This felt like betrayal to her, and she loved Brian too much to even entertain the idea. Sometimes, solutions to problems happen when you least expect them. This one happened at the office party. The occasion was the company's acquisition of their rival. Brian had successfully landed the deal.
Up until then, she had only heard of Stacy, but she never met the woman. Monica didn't like to go to the office because, truth be told, she missed being a part of it all and this would make he want it more. He missed that, but she also loved being a good mother to her children. She couldn't help but notice Stacy, who was wearing a pink French Maid's outfit despite the fact that it wasn't a costume party. She said she was protesting the fact that Brian overruled her idea for the party.
It was easy to see what Brian and everybody in the office liked about the younger lady. She was easy to get along with. She was flirtatious and friendly. This lady was in many ways running the office. Brian still called the shots in what needed to be done, but some decisions were made by Stacy. Plus, she was the one who motivated the employees to make it happen. It wasn't so much that she ordered people around. They wanted to do it to make her happy.
Stacy seemed to make time during the party to have one on one conversations with everybody except Monica, who noticed that fact. She finally approached Stacy. "Have you been avoiding me Stacy?"
She smiled that same smile that had everybody melting, and Monica felt a tingle. "Not at all. I figured I'd get everybody else out of the way first and save the best for last."
Monica blushed. "Oh, I'm sure you don't mean that."
Stacy took her hand. "Can I be honest?"
"I wish you would."
"Well, your husband is always going on and on about you and how much he loves you and he's building this company up to make sure you and the kids have everything you need."
Monica was surprised by the revelation. "Really?"
"Absolutely, " she replied as she squeezed her hand gently and gave her a look of genuine adoration. "And, I must confess, you are even more beautiful in person than the pictures."
Monica couldn't help but blush from the flattery. "Oh, but I'm sure you don't mean that. The way my husband goes on about you, I thought you two were having an affair."
Stacy smiled and wiped some of her blond hair out of her eyes. "Your husband is a sweet man and very attractive, but there's somebody else I'm interested in."
Monica smiled at the gorgeous woman in front of her. "I'm sure he's a lucky man to have the attention of you."
Stacy again grabbed her hand with both hands this time and squeezed it. "It's not a man I'm after, sweetie."
Monica blushed and panicked in that moment. "Oh, I um... Could you excuse me."
Monica went walking to the ladies room and into a stall. Moments later, Stacy entered the room and locked the door. She stood in front of Monica. "I hope I didn't alarm you, but I wanted to tell you. You seem so sweet, and I feel like I can tell you anything. I feel like I need you tell somebody, but I can't."
Monica smiled nervously. "Well, you’re standing in front of me in a bathroom stall, so you might as well tell me."
Stacy reached under her dress and pulled something out of her panties. "Perhaps I need to show you."
She revealed a rather large eight-inch penis. Monica looked into her eyes in astonishment and saw the lady's vulnerability. "You're a..."
"A transsexual."
Monica was speechless. "I don't get it. Why are you telling me?"
"I don't know. I kind of wanted to tell Brian, but I was nervous about it. Then I started thinking about you and what he says about how caring and understanding you are. I just thought I could tell you." Stacy stared at her, but she got no response. "I shouldn't have done this, should I? God I'm gonna get fired."
Monica thought about how this gorgeous woman revealed her most intimate secret to her. Nobody at the office knew it, but Stacy trusted her. She also thought about how she would like to experience sex with a big cock inside of her, and there was one pointing in her face. If she didn't act now, this lady might walk out of their lives forever, filled with shame for being rejected.
Monica leaned into the cock in front of her and took it inside her mouth. It was quite a bit bigger than her husband's and attached to a feminine body. It was at once confusing and arousing to her. "Oh my God, I was hoping you would like me, " said Stacy as she gently ran a hand through Monica's hair. "I've been thinking some dirty thoughts about you."
Monica was savoring the taste of her magnificent she cock as she sucked the tip. "Like what?"
Stacy smiled seductively. For one thing, burying this thing deep inside your pussy. I bet I can hit you in places he can't."
"Oh my, " she was blushing again as she kept sucking. "I thought transsexuals liked men."
She pulled out of Monica's mouth and guided her to the sink counter to have a seat on the edge. "Not all of us." She kissed Monica. "I'm not against a good cock, but I prefer pussy. More specifically, your pussy."
Monica removed her already wet panties. "Well, then take it. I want you inside of me."
Stacy gently entered Monica and felt the warm embrace of her womanhood. This was truthfully something she wished she was born with. She'd even considered surgery, but she worried about not feeling anything during sex. Her cock still gave her pleasure, and she found that women enjoyed it inside them. Since she could feel that pleasure and still look like a woman to the outside world, she resolved to keep it that way for now.
With her cock inside Monica, she embraced her in a passionate kiss. Their hands explored each other's backs. The feeling of their breasts pressed up against each other was a unique sensation to Monica, but she was very turned on by the contradictions. She squeezed Stacy's girlie love stick inside of her as Stacy continued her gentle thrusts. Despite this being their first actual meeting, this was more of a love making session than a fuck.
The love making went on for a few moments before Monica felt something she hadn't felt with Brian in a long time. As she began to have an orgasm, Stacy came inside of her. They climaxed together and kissed deeply as their tongues engaged in a sensual dance. Monica came out of the sexual haze first and started to worry. "Oh my God. What do I tell Brian?"
Stacy seemed unphased by all of this as she kissed Monica again before pulling out of her. "Do you trust me?"
Monica looked into her beautiful blue eyes. "Yes."
"Good, then lets gets back out to the party. I'll handle Brian at work on Monday." Stacy exited the ladies room first as if nothing had happened. She went right back to flirting with everybody.
Monica couldn't get the memory of being fucked by Stacy's big cock out of her mind, and she carried a bit of her inside of her. When she and Brian arrived home that night, she ordered Brian to eat her out again. He was very thorough. Whether or not he could taste Stacy on her pussy, he didn't say.
At the office on Monday, Brian noticed Stacy staring at him most of the day. What was it, he wondered? Could she tell he was wearing a pink thong? The way it rode up his crack was a constant reminder that he was wearing it. Could she make out his pink bra? He didn't think it looked detectable, but he was starting to have doubts. Stacy chose to wear a much more secretarial looking black skirt suit, while also keeping her blond hair tied back in a bun.
It was when the last employee left that Stacy entered his office. "Will there be anything else, Brian? Do you need any dictation done?" She emphasized dick in dictation.
He squirmed in his chair. He just wanted to get out of there without being noticed. He was sure she knew something. "No. I'm fine. You can go."
She walked to his side of the desk and leaned on his desk. "Well, maybe I have some dictation for you to take."
He looked at her face and knew something was going on in her mind. What was she up to? "What's on your mind, Stacy?
"The erotica line of books."
He sighed. "This again? Stacy, I think you've done a great job of getting that started, but I just don't know."
She smiled at him to try to set him at ease. "Brian, you do know that it's not just people who are in vanilla relationships that read this stuff, right? The gay community reads it. There's potential in the BDSM market. There's the transgender community. And, of course, sissies read it, and they love to read a hot story."
There was something in the way she looked at him when she said sissy that had him squirming. In fact, he became even more nervous. "I just don't know if we're the right publishing company for that."
"I think it would be a hit. It's a niche market, but we can test the waters." She grabbed a pen on his desk and started moving it between her fingers as he watched her perfectly manicured red fingernails move. "Besides, we received an inquiry from an author writing a story about a sissy and his Mistress. It's really quite good, and I bet you'd love it."
He did not like where this was going at all, and he shifted uncomfortably in his chair as his penis betrayed him. "Oh really. And who would write such a story?"
She stood up and walked around the room, delighting in teasing him. "There's this author that you published some 15 years ago. She had a knack for romance novels. It's been a while, but she has a really good idea about a sissy who needs to be put in his place. It's cute actually. The sissy goes out in public dressed as a woman and looks somewhat convincing."
Brian's face went white as he realized who she was talking about. "I don't know, Stacy. Maybe we could give it a shot to test the market."
She walked towards him and leaned over the other side of the desk, giving him a good view of her cleavage. "Tell me something Brian. Have you ever thought of going out as a woman in public?"
He blushed. "What would ever give you that idea?"
She smiled and stood up. "It's just a question. I'm curious." She walked to his side of the desk and stood there. "Tell me, are the panties riding up your ass crack today, sweetie?"
She giggled. "I've known for a while dear. I don't think the people here can tell, but I know the signs. She really picks out a nice lipstick for you when you have your lipstick days. Very subtle. But, Channel 5 is kind of pushing it, I mean, you want them thinking you are a man, right?" She winked.
He was caught, and yet he tried to deny it. "I don't know what you're talking about."
"I tell you what, " she bargained. "Show me you aren't wearing panties or a bra and I'll leave this job and you won't see me again. Show me you are, and we'll try my erotica idea."
He shook his head. "No. I can't."
She sighed. "Sometimes, confession is good for the soul, Brian. You show me the truth, and I'll tell you a secret that I've only shared with one other person. In fact, you may fire me after that."
He reached for her hand. "Stacy, no. Don't even joke with me about that. I need you here. You've meant the world to this company, to me."
"So, strip for me, Missy. Show me."
He was still unsure about this. "You... You won't think I'm some sort of freak or something and quit on me?"
She giggled. "Who said being a freak was necessarily a bad thing? Besides, I kind of like the idea that you are a panty wearing sissy who fantasizes about being a woman."
Gradually, he removed his clothes to reveal the pink thong and matching bra. With his shoes and socks off, his hot pink toe nails were exposed. "Oh my God, I love those toes, " she said with a smile.
"Show her the tattoo on your ass, " came a female voice from the door. It was Monica.
"Oh my God, you have a tattoo? Show me."
He blushed. "Monica!"
She glared at him. "Oh, stop crying and show it to her, sissy."
He turned around and bent over to reveal a pink heart that read Sissy For Life. Above it in red was the word Monica's. "Aww, how sweet." Stacy smiled at him. "That is adorable. I knew you loved her, but to proclaim yourself Her sissy? That's sweet."
He was about to put his clothes back on when Monica spoke again. "Sit down. We're not done here yet."
He immediately sat in his chair. "We're not?"
Monica walked over to Stacy and kissed her on the lips. "No, we're not. I made a promise to you that I intend to keep. I told you I would tell you when I found another cock out there. Well I did."
He was surprised. "You... You did?"
Stacy giggled. "She did."
"Oh, " he replied, trying not to sound too sad.
"Well, " Monica continued. "I feel bad about it, because I kind of got laid before I told you. It happened so suddenly that I had no time to think about it."
"It's true, " Stacy nodded. Brian looked over at Stacy, wondering how she knew about his wife's tryst with another man.
Monica smiled flirtatiously at Stacy. "Anyway, it occurs to me that the best way to make it right is to have you please the cock of my new lover too. That way, we've both shared a similar experience."
Brian shook his head. "That's okay, sweetie. I don't need to do this. I'm okay with it."
She walked over to him and kissed him. "Well, maybe I don't want you to just be okay with it." She walked over to Stacy and kissed her sensually. "Maybe he needs to know how it felt to please such a beautiful cock."
Brian was confused. "I don't get it."
Stacy began removing her clothes. "Remember when I said I had a secret?" She removed her top and bra to reveal a nice set of DD Breasts. Then came her skirt and panties, leaving a semi erect eight-inch penis. It was smoothly shaved. "I'm a transsexual woman."
He stared transfixed at the beautiful woman with the big cock, unsure of what to say. She was still beautiful to him. He knew he still needed her there. "Why didn't you tell me?"
She laughed. "Yeah right. I have no experience, no formal education and I'm a tranny. Would you have hired me?"
He was speechless as she approached him. "Thank you for not lying to me just now."
He looked into her eyes, those blue eyes that played such a big part in his decision to hire this determined and intelligent woman. "You really mean a lot to me and my company. I can't imagine maintaining things without you."
"There is one way you can thank her, Brenda."
Stacy stood in front of him, looking down at him for his response. "Suck her cock for me, " Monica ordered. "Trust me, sweetie, it tastes great."
Stacy turned her head to say thank you as she was greeted by Monica's kiss. In that moment, Brian was sucking his first cock. Not the cock of some hairy man, but a beautiful, feminine transsexual woman. He had already established a friendship and good working relationship with her, and he hoped this wouldn't jeopardize it.
As he was licking on her beautiful cock head and tasting his first traces of her pre release, Monica was stripping naked and took a seat in the other chair by the desk, fingering herself. Brian let Stacy's moans be his guide as he worked his tongue around her sensitive areas and bobbed up and down. "That's it baby. Are you ready for my new lover to feed you her cum?"
He didn't answer as he the stronger taste let him know that she was getting close. "I think she wants my cum, " she said with a look of pure pleasure in her eyes. "Oh yeah. Here it comes baby. Swallow it all."
When he finished sucking her clean, he collapsed in his chair, but Stacy looked over at Monica. "Are you just gonna let your wife sit over there fingering herself, or are you gonna show her what a good pussy licker you are?"
Soon, he was on the floor in front of the chair with his face buried in his wife's neatly trimmed pussy Stacy was kissing her and fondling her breasts. "I could get used to this, " Monica proclaimed.
"Me too, " Stacy replied between kisses.
As Monica had a mini orgasm delivered by Brian's talented tongue, Stacy's cock was alive again and inside Monica's mouth. Monica was in ecstasy when she got up and walked to the desk and bent over it. "Brenda, dear, guide our sexy lover's cock inside of me." On his hands knees by the desk, Brian kissed Stacy's cock and positioned it in front of Monica's quivering pussy.
Brian was incredibly turned on at the sight of his gorgeous secretary's shaft disappearing inside of his wife. He had no idea until today that Stacy was transsexual, and it made no difference to him on a professional level. On a personal level, he knew that he and his wife had found a lover who seemed all too eager to join them in their sexual adventures. He couldn't be happier.
By the sounds of his wife's moans and the way she was breathing, he could tell she was enjoying a big orgasm. As Stacy continued to plow her, Monica stopped her. "Stacy, honey. I'm gonna get over here so my sissy can lick me. I think your next load should be for him, don't you?"
Stacy pulled out and pushed his head onto her shaft. "Clean it sissy, " she instructed as Monica moved across the desk. "Are you saying you want me to make him my pussy boy?"
"Unless you don't want to."
She looked at Monica and then Brian. "The thought has crossed my mind more than once, to be honest with you. And, I know panty boys like him crave it. Okay, bend over the desk sissy."
Brian offered no resistance this time. He wanted it. "Oh shoot. I don't have any lube, " Stacy admitted.
Check my purse, " Monica replied as her husband's tongue was probing her pussy again. "I had a feeling we'd need some today."
Stacy laughed. "I'm sure you did." She lubed his hole up well and was soon pushing her monster cock into his tight hole. With each inch came some pain as Brian got used to it. From Stacy's perspective, it was pure pleasure. She preferred to give it, but occasionally it was nice to receive it. "Does my pussy boy like his secretary’s cock up his ass?"
Brian kept licking his wife's sweet love box until she ordered him to answer. "Brenda, it's impolite not to answer. Don't be rude."
"Mm, I love it, " he replied before going back to work on his wife.
Stacy looked Monica in the eye and had a satisfied smile on her face. "That's what I thought. He has a nice tight butt. I could get used to fucking this hole."
"Well, if he gets too uppity from now on, you know what to do, " Monica replied with a wink.
The pleasure continued to build for Stacy as the sissy's violated hole felt good around her hardness. She could tell the way Brian was moving his ass that he was into it, but she was pleased with herself when his ass started to spasm, indicating that he was in the midst of an anal orgasm. "Oh my God, Monica. Your sissy is cumming. I think he likes it."
Monica's head was leaning all the way back with her eyes glazed over in pleasure. "Oh God.... He's not the only one." Monica was having her third orgasm of the day.
Soon, Stacy joined them as she unloaded her seed inside of her boss's ass. She leaned in to kiss him on the back of the neck. "I know you are my boss, but now this makes you my bitch, Brian. You're my pussy boy."
The three composed themselves and were later sitting on the couch in the lobby, still naked. "Of course, you know that Stacy has the real cock in this relationship now, right sweetie, " she asked her husband as she kissed him?
He thought about how Stacy made him cum by fucking him without him touching himself. "I do."
"You were amazing, Brian, " She kissed him deeply. "You are a natural bottom. You've never done this before?"
"No, never."
Monica giggled. "I have a feeling Stacy has a voracious appetite for sex."
Stacy nodded. "I do. I love to fuck."
Monica kissed Stacy passionately. "So, we need to be ready for her when she needs release inside one of our holes."
"Even here at the office, " Brian asked, noticing Stacy getting aroused again?
"Especially here at the office, " Stacy replied with a grin. "I build up a lot of tension here and need release."
"But..."
"Sweetie, you love me, and you've already chosen to submit to my desires. " she said with another kiss on her husband's lips. " I say we have to submit to the real cock in our relationship, and that's Stacy."
He kissed his wife, "Yes dear."
Stacy grinned. "Good. Now that that's settled, how about you suck my cock some more. I want to see how good your wife's ass feels."
The three enjoyed another couple of hours of passion at the office. True to her sexual appetite, Stacy would sometimes show up to visit Monica during the day for an afternoon lovemaking session, or even at night, She did take Brian's ass when she wanted it, and he never resisted. There were lots of exciting times between the three of them, including Stacy's insistence on having monthly office costume parties and dressing Brian up as Brenda, completely femme in public. Of course, these are stories for another time.
