Lost Suitcase Adventure Pt. 03

He was so sweet when we made love for the first time. I secretly wished I had gotten together with him all those years ago. He had a nice sized dick and used it well. We made love and then we fucked! I even gave him my ass once as a thank you. Jesse's trip was becoming the best weekend of my life. I was sorry it was about to end.

I was texting with Tom all day and he couldn't stop talking about last night. He was asking if we could do it again in the future. We had mentioned it only being a one time thing, and I wasn't sure Jesse would want to go for it again. I told Tom that he was the man in this scenario and it was up to him to do the convincing. I had done enough in setting everything up and it was time for my husband to take charge if he wanted things to continue.

Fortunately Jesse made it easy for all of us. He got dressed in lingerie and waited for us in our bed. Tom wasted no time and started fucking Jesse while I blew him. Then Tom dropped the bomb. He made Jesse promise to be our girl every time 'She' came to visit. He caught me off guard with the way he did it, but he had stopped fucking Jesse until 'She' answered. 'She' agreed and just like that my best friend Jesse was now a girl when she was in our house. Not only did Tom get her to agree to be a girl when she was with us, he got her to agree to dress up for us at home and work and send us pictures. He was really taking charge and I loved it.

When it was time for Jesse to leave, I had her wear a pink thong, garter belt, and black stockings under her jeans on the plane. I told Tom I had a surprise for him and he should text Jesse to send us a picture from the airplane bathroom. When Tom saw what I did, he was so turned on that he grabbed me and fucked me senseless.

Tom continued to text her for photos of her lingerie and each time she responded right away. He liked to tease her with dick pics and I would send her pictures of my bare breasts. Tom had been requesting pictures for three months when Jesse totally surprised us. First she sent us her usual lingerie picture, but then she sent one with full makeup, a wig, and a short black dress. This had started as an idea for a threesome, but the fact that she was buying her own clothes made me realize we changed my best friend forever.

It got better from there when Jesse's company opened an office not too far from us. We didn't even hesitate to move her into our home. Jesse had to fly down in male clothes because of ID reasons, but I brought a change of clothes to the airport. She quickly changed in the family restroom and wore a dress and heels to her new home. Once we arrived Tom greeted us both with a huge kiss and we sat down to talk.

"I am so happy you're here," I said.

"Me too," she said, "This is like a dream."

"We're happy to have you here," Tom said, "Jessica and I were talking and we came up with some ground rules."

"Ground rules?" She asked, confused.

"Not rules," I said, "More like suggestions we can all agree on."

"Call it whatever you girls want," he said, "Anyway, first off we moved the bed out of the room you stayed in last time. That is now a closet and dressing area."

"Sounds good to me, but where will I sleep?" She asked.

"With us!" I said, "Our bed is your bed!"

"Whoa, I didn't expect that, but I think we can make that work," she said.

"Next, when you're in the house you are a Girl and you will dress like one. No exceptions. The only time you can wear male clothes is to work," Tom said.

"Um ok, I kinda figured," she said.

"Are you really ok with that?" I asked, wanting to be nice and not act like we're controlling her life.

"Yeah, I love being your best girlfriend," she said.

"Also you will do your best to avoid us when you're not dressed as a girl. I don't want to ruin the illusion. The back door is right next to your new dressing area, so you can go in and out that way," Tom said.

"I'll do my best," she said.

"Next, we want you wear lingerie under your suits. We want you to be reminded that you're our girl all day," he said.

"Um, I'd be a little worried about wearing a bra to work. I don't want to get caught," she said.

"Ok, how about panties and stockings underneath your suit pants, that should work for us," Tom said.

"Deal," she said, "Anything else?"

"Yeah, I've got a massive hardon that needs taking care of!" He said.

"Tom!" I yelled.

Jesse dropped to her knees and said, "No problem, that's what I'm here for!"

She unzipped his fly and took his entire length into her mouth. She must have been practicing to take him so deep like that. She started bobbing up and down and he was moaning. This was going to be a great arrangement. While I didn't mind sucking Tom's dick, he always took so long to cum and shot so much in my mouth that it was going to be nice to have my best friend there to share the duties.

Jesse was really going to town and I felt my panties getting damp. I lifted my dress and played with my clit while my new roommate blew my husband. I was enjoying the show when Tom yelled out that he was cumming. Like a good girl Jesse swallowed it all. When she picked up her head she saw what I was doing.

"Don't worry, I'm here for you too!" She said to me.

She pulled my panties down and started tonguing my clit. Wow, this really was going to be a great arrangement. I remembered from the last time how good Jesse was at eating pussy and she didn't disappoint. She had me panting and screaming before I had a massive orgasm.

"Well that was certainly nice welcome home," Tom said.

"You're welcome," she said, laughing.

"Why don't we have some dinner and then we can break in the bed. I've been dreaming of that ass!" Tom said.

"I can't wait," she said.

"All my life I've wanted a best girlfriend, and now I find out she's a slut," I said, laughing.

"Takes one to know one," she said.

"I guess you're right," I said.

After dinner we took Jesse to bed and had what had to be described as a sex marathon. Tom fucked Jesse three times and then they each fucked me once.

After the first night our bedroom activities changed a bit. Jesse didn't fuck me as much, maybe just once a week and without Tom around. Tom was focused on Jesse being our girl and our girl didn't fuck his wife. Tom would fuck me and Jesse and she would go down on me. Jesse never complained, so she must have been fine with the arrangement.

A couple months later Jesse was riding Tom cowgirl and I was watching. Jesse had been fucked in every position and she said she liked cowgirl the best because she had the most control. As she was fucking him Tom reached up and grabbed her nipples. He squeezed them which caused her to shout out. He pulled her down and started sucking on them. When he stopped Jesse sat back up and kept riding.

"Wouldn't it be great if you had a little more up there?" Tom asked.

He must have caught Jesse off guard because she stopped moving and just said, "Um."

"Think about it. How hot would that be to have a set of real boobies? You wouldn't have to stuff anymore, and there would be something for us to play with," He said.

Jesse didn't react. I guess that didn't sit well with Tom and he put his hands on her waist and lifted her off his dick. Jesse whimpered as he left her ass. She was struggling to get back on, but he wouldn't let her.

We hadn't discussed this at all. I actually thought it was a good idea, nothing too big to cause issues at work, but enough to play with like Tom said. I'd love for my best friend to have boobs and I bet she would too. She could show off her cleavage and no more inserts. Plus I've always wanted to suck on a nice pair of titties.

"You didn't answer me," he said.

"I don't know what to say," she said, "Please, I was just about to cum."

"All you have to do is answer and you can. Should we get you a pair of boobies?" He asked.

"But work?" She whined.

Tom was fed up. He's not a violent person at all, but he knows how to get what he wants. He grabbed Jesse and flipped her onto her knees. She shrieked and I was scared for her for a second. Then Tom looked at me and winked and I knew it was ok. He got in position behind her and put the tip of his dick back inside her. She moaned in relief, except he didn't move, he held still for what I'm sure seemed like forever for Jesse.

"Please fuck me! I need to cum," she pleaded.

"I'll ask again, should we get you a nice pair of boobies for us to play with?" He asked.

"But how?" She whined again, moving her hips, trying to get him inside her.

He thrusted in to the hilt to a pleasing moan from her and then pulled all the way out to the groan of disappointment.

"Say you'll get boobies for us and I'll make you cum," he said.

"You better answer him," I said, playing along.

"If I say yes will you please keep fucking me?" She asked, totally exasperated.

"Yes," Tom said, pushing back inside of her.

Without getting her answer he started to pound her again. They were getting into a good rhythm when he stopped again.

"Say it," Tom said and started fucking again.

Jesse yelled out, "I want boobies!" As she came hard.

"That's my girl!" Tom yelled, as he blasted his load inside her.

Tom went into the bathroom and Jesse was lying next to me.

"So you really want boobs, huh?" I asked.

"I would've agreed to anything right then," she said.

"You really have become a slut," I said, laughing.

"Hopefully a slut without boobs that aren't too big," she said, "I still have to be professional at work."

"You know we wouldn't do anything to hurt you or your career, but we also make enough money that you don't have to work," I said.

"You know I love my job, and it's nice to contribute around here. I don't want to just be a stay at home fucktoy," she said.

"Hey!" I said, giving her our typical punch in the arm. "You'll pay for that!" I said, giggling.

Tom came back from the bathroom and asked, "So what are my girls talking about?"

I said, "Jesse and I agreed she should get a nice pair of B cups, small enough to hide under her work clothes, but big enough for us to play with and show off some cleavage in her tops and dresses."

"Really?" Tom said, "That would be awesome!"

Jesse gave me a look and I gave her a mischievous smile back.

"Anything to make you guys happy," Jesse relented.

THREE MONTH LATER -- JESSE'S POV

I had resisted, but having boobs was so much better than wearing the inserts. They felt awesome too! The first time we all got to play with them, Tom titty fucked me while I licked the head of his dick and Jessica blew me.

As much as I enjoyed having breasts, it was Jessica that loved them the most. She would make every attempt to touch them. We would be sitting on the couch and her hand would find itself inside my shirt rubbing my nipples. More than anything she loved to suck on them. My nipples were as sensitive as ever and I loved the attention!

One day Jessica jumped in the shower with me. She started to wash me and paying specific attention to my breasts.

"You know Tom is working overnight so it's just you and me tonight Sweetie," she said.

"That's great. What do you have in mind?" I asked.

"I was thinking we could 69 and then you can fuck my brains out while I suck on your tits!" She said.

"Whoa, that sounds great. I'll try to get home early!" I said.

I got out of the shower and started to get home from work. I had mastered controlling my erections in my panties, but my nipples were another story. They were still rock hard from our shower and I couldn't stop thinking about what was going to happen tonight. When I put my dress shirt on, my nipples were protruding and there was no way it was going to fly. For the first time since I've been dressing up, I made a bad decision. I put on the bra that matched my panties and wore it to work. From the side you could make out a small bust, but once my jacket was on, they were concealed. Most importantly my bra covered my still hard nipples.

Work went fine and nobody noticed anything. At least that's what I thought. I texted Jessica I was on my way home and when I got there she was naked in our bed. I went down on her while she blew me and then she finally relieved my aching nipples by sucking on them while I fucked her to multiple orgasms.

TWO WEEKS LATER

It was a Sunday night and I had only worn a bra to work the one time. The three of us were sitting on the couch and watching TV when a text came through from an unknown number. There were 3 pictures with a caption of 'Looking hot sissy!' I excused myself and said I had to go to the bathroom.

I closed the toilet lid and sat down. As I analyzed each picture I was shocked and embarrassed. The first one was from the day I wore the bra to work. At one point I forgot to keep my jacket on and the mystery texter had taken a picture from my side that clearly showed the curves of my breasts.

The second picture was a direct shot of me with my bra clearly showing through my shirt. I had no idea it was visible. When I looked in the mirror at home that day everything looked fine. The third picture was from another day, but it showed a close-up of my panty line through my suit pants. Somehow this person caught me on the one day I happened to wear a bra and the other day when I didn't wear a thong. It had to be someone from work, but who?

As I was looking at the 3 pictures over and over 2 more came in. These weren't as subtle. They were taken through the window of my dressing room at home. The first was of me in full makeup, my wig, and a dress. The second was a close --up of my bare breasts. Now I was upset. It was one thing to try to expose me at work, but it was another to come to my home and take pictures of me through my window.

I responded with a nasty text, "WHAT DO YOU WANT FROM ME?! WHEN I FIND OUT WHO THIS IS THERE'S GONNA BE A BIG PROBLEM!"

The response was calm, "Relax sissy, I just want to have a little fun. Besides you don't want everyone at work to know your secret, right?"

I was being blackmailed. My instinct was to tell them to go fuck themselves, but then I thought I could diffuse the situation on my own. I certainly didn't want Jessica and Tom to find out.

"So what do you want? Please don't tell anyone at work," I replied.

"Like I said, I just want to have some fun. Tomorrow I want you to stay late. Wait until everyone leaves and I want to see in your office, wearing your cutest bra and panties, and don't forget your wig and makeup too. I want to see the real you," the text said.

Fine, I thought to myself, I would play along this one time. I was still the boss and I wasn't going to let one of my employees mess with me.

I just replied with, "Ok."

I walked back to the couch and I was nervous. Luckily Jessica and Tom didn't notice.

I didn't sleep well that night and I kept thinking about what was going to happen. I loved my job and didn't want anything to happen to it. I wasn't ready for my work life and my home life to collide, but this person was pushing it that way.

I got dressed in a black bra, thong and stay up black stockings. I picked a dark blue shirt to go with my suit to make sure nobody else would see my bra. I put makeup in my purse and then put the purse and my wig in a duffle bag.

The day seemed like it took forever and when the last person left I went into the en-suite bathroom in my office to apply my makeup. I put on my wig and waked out to see Sam sitting on the couch in my office. He had his phone out and was snapping pictures of me. Sam was my second in command. We never really got along, because he thought he should have my job. We made due for the sake of the company, but I always knew he was out to get me. Now was his chance.

"What do you want from me?" I asked, standing in front of him.

"You clean up nice for a sissy. You have a tight little body and nice long legs. I can't believe you've been hiding those beautiful breasts from the world. You should be flaunting them. Why don't you give me a spin so I can see the rest," he said.

I turned around. It was nice that he was complimenting me, but I was pissed this guy was blackmailing me. My mind was going a mile a minute thinking about how to get out of this.

"Wow, nice tight ass too," he said and slapped my cheek.

I yelped and sat down.

"So again I'll ask, what do you want from me?" I asked.

He unzipped his fly and said, "I've seen your body, now I'm curious about how your mouth feels."

"Fuck off!" I yelled.

"Take it easy sissy, I'm sure you've sucked cock before?" he said.

"So if I blow you we're done?" I asked.

"Yep," he said.

"One time and we're done?" I asked.

"Yep, you have my word," he said.

There was no way I trusted this guy, but I had no choice right now. I had no doubt he would expose me to the rest of my employees and corporate. I knew I had no choice but to blow him and then reassess my options.

"Fine, stand up and drop your pants," I said.

I had only seen Tom's dick and my own, and Sam's dick was smaller than both of ours. I wanted to get this over as quickly as possible so I started sucking my second dick ever. I blew Tom all the time and I had gotten good at it. I had a feeling that Sam didn't get much action so he probably wouldn't last long.

I was right. I gave him a couple of bobs with my head while using a lot of tongue. I took him as deep as I could and he just reached my throat. It wasn't even two minutes and I could feel him tense in my mouth. The bastard didn't even warn me he was going to cum, but I knew it was about to happen. He yelled out and blew his load in my mouth. As he came he put his hand on the back of my head and held me in place. I had no choice except to swallow it all. What an asshole!

I was still sitting on the couch and he was breathing heavy with his eyes closed. I looked to my left and his phone was sitting there, unlocked on the couch. This was my chance. I grabbed the phone and raced into my bathroom. I locked the door. As he started banging on the door I was already looking in his photo album. I deleted the pictures from today and the ones he had texted me. When I was done I opened the door and handed him the phone back.

"I think we're done," I said, "Now get out of my office!"

"I think I'll stay a while," he said.

"Fuck you! You got your blowjob and I think you figured out that I deleted all the pictures," I said.

"Yeah, but you don't realize I have the upper hand now," he said.

"What do you mean?" I asked.

"Sit down and I'll tell you," he said.

I sat down with a nervous look on my face.

"We would've been done. I gave you my word and I meant it. I don't know why you didn't trust me. One blowjob, that was the deal, but then you pulled the stunt of grabbing my phone and deleting the pictures. At least you thought you did," he said.

"What the hell are you talking about?" I said.

"The cloud, sissy! My phone is setup to automatically backup my pictures to the cloud. The second I snapped those pictures they were uploaded. Deleting them off my phone did nothing!" He said.

"Fuck!" I said.

"So here's the new deal...This is going to become a daily arrangement. Once everyone leaves, you get dressed up for me and blow me. As long as you're a good sissy this stays between us," he said.

"How long do you expect me to do this?" I asked.

"Until I say so," he said.

I had royally fucked up and all I could do was say, "Ok."

"Don't be sad sissy, you're a great cocksucker and you made me feel so good. You may even come to enjoy this arrangement. I know I will!" He said as he walked out of my office.

I sat for a minute to collect my thoughts. Part of me wanted to tell Tom. The problem was he would kick the shit out of Sam and then my career would be over. I would have to suck it up, I guess literally, until I came up with a new plan. When I got home I was so horny that I dropped to my knees and blew Tom at the dinner table while he ate.