I was on my knees with Tom thrusting his huge dick in and out of my asshole. I still couldn't believe I was enjoying getting fucked in the ass. Not only was I enjoying it, I had requested it. My pleasure was heightened even further because my Best Friend Jessica was upside down on her back beneath us. She was giving me a masterful blowjob while my tongue was bathing her clit.
"Damn Girl! Your ass is still so tight! I thought that after the first three times I would have opened you up!" Tom said.
His words made me feel so hot and desired that I started fucking him back as hard as I could. Jessica was doing her best to keep sucking me, and I was still making sure her pussy was getting the attention it deserved.
"You're really into this, aren't you Jesse?" Tom asked.
It was the first time he'd used my name in bed and it caught me off guard. I lifted my head off of Jessica to respond.
"I never thought I'd say this, but I love getting fucked! Your dick feels soooo good," I said.
"Then I have a question. Will you agree to be our girl every time you visit?" He asked. He had stopped fucking me and was holding himself balls deep inside me.
Now I was really surprised. This started as a one time thing last night and I decided to do it one more time tonight. Now he was asking for me to fool around with them every time I saw them? Was this his idea or was Jessica involved too? My mind was going a mile a minute and his huge dick was lodged all the way up my ass. That was short lived though, because when I didn't answer right away, he pulled all the way out. Not only that, Jessica moved her mouth off my dick. I groaned in disappointment as both sources of pleasure had stopped.
Tom spanked my ass hard and asked, "So are you going to be our girl or what?"
I couldn't focus on his question because all I was thinking about is getting him back inside me. I was moving my ass around and reaching behind me to grab his dick, trying to accomplish that. I heard him giggle as he realized what I was doing. Meanwhile Jessica was lightly licking my dick, teasing me instead of sucking me. They were driving me crazy. Tom finally pressed his head against my rim and held still. I tried to push back on him, but he grabbed my hips and held me in place.
"I think you better answer," Jessica said to me, "Do you want to be our girl or not?"
THIRTY MINUTES EARLIER
My suitcase had arrived, but instead of changing into my normal clothes, I went right for the bag of goodies Jessica had bought for me. It was a Victoria's Secret bag full of lingerie. I had been wearing a white bra and thong all day underneath one of her dresses. I pulled out a white garter belt and stockings out of the bag. I pulled off my dress and added the accessories to the bra and panty set I was already wearing. I checked my makeup in the mirror and walked into their bedroom. I sat on their bed with my back against the headboard and waited. Not too much later I heard them walking down the hallway. They paused at my room and when they saw I wasn't there, they walked into their bedroom. When they saw me all decked out in lingerie on their bed they both smiled.
I said "I'd like to spend my last night having fun in here with you guys again if that's ok."
Jessica quickly pulled her dress over her head and Tom dropped his shorts and boxers. Jessica slowly removed her bra and panties and joined me on the bed. She started kissing me and we made out as Tom finished getting undressed and joined us on the bed. Kissing Jessica was awesome. I still wasn't used to it, but she was the best kisser I've ever been with.
We stopped kissing and Tom said, "If you want to share our bed again its going to be a little different than last night."
"Okayyyyy," I said, sounding confused.
"Don't worry Sweetie, you'll still get to play with both of us and you'll definitely get off multiple times," Jessica said.
"Yeah it's just that tonight we're in charge," he said.
"But of course if something hurts you just let us know. We're not into pain or leaving bruises or anything," she said.
"So you want to use me for your pleasure instead of tit for tat like last night? That sounds so...hot!" I said.
Tom grabbed Jessica's breast with one hand and my bra covered man boob with the other and said, "There will be plenty of Tits!
We all laughed.
"Is that ok with you Sweetie?" Jessica asked.
"Since this is my last night and I'll probably never do this again, I'm in" I said.
"I have a feeling that after tonight, you're going to want more and more," Tom said.
"Me too!" Jessica said. "Now best friend of mine, help me suck my husband's cock!"
I crawled over to Tom and Jessica was on the other side. She licked the side of his dick and motioned to me to do the same. We met at the tip and started to kiss. We were making out around Tom's dick. We would take breaks and alternate taking him in our mouths. As we were blowing him together he was sitting back and enjoying the view, occasionally shouting out 'Oh yeah!' or 'Suck that dick!' He began to get harder and just as he was about to cum she pushed his dick it into my mouth and I swallowed his entire load.
Jessica excused herself to go to the bathroom and left me and Tom alone on the bed. He didn't say anything and started to feel me up. He was rubbing my man boobs through my bra and my nipples and dick were getting hard. He noticed and pulled me in for a kiss. This wasn't our normal kiss. This time he was strong, like a man kisses a girl. I was enjoying playing the submissive role, especially because he was such a great kisser. Without stopping our make out session he rolled us over, landing on top of me. In this position I could feel his dick getting hard again while pressing against mine.
"Ready for me Baby," he asked.
"Mmmmm," I replied.
He flipped me onto my knees and pulled off my panties, throwing them across the room. My dick was rock hard and there was a string hanging out of my ass.
"What's this?" He asked, as he pulled on the string and laughed hysterically.
"Um" I started to say, totally embarrassed.
"Have you been wearing this all day?" He asked, still laughing.
I was getting a little upset and said, "Well you shot so much up inside of me, Jessica didn't want me to leak all over the place!"
"That's my wife, always thinking," he said.
He yanked on the string and pulled the tampon out quickly. I gasped at the sudden feeling.
"Ahhh. I feel so empty," I groaned.
"No worries, I'll fix that!" He said loudly.
He pushed his dick against my hole and pressed in until he was balls deep.
BACK TO THE PRESENT
"I think you better answer," Jessica said to me, "Do you want to be our girl or not?"
Now I knew she was in on it too. Had she planned this the whole time, or did they just come up with it together after last night? I guess it didn't matter, because either way I wanted this.
"Okay, Yes! I'll be your girl! I yelled. "Just keep fucking me with your amazing cock!"
"So every time you visit I can expect to enjoy both of my girls?" Tom asked.
"Yes!" I screamed.
He pushed his cock all the way inside me and Jessica took me all the way into her mouth at the same time. They both held still and I finally felt wonderful again. This was unfortunately temporary, because they both pulled out again, and asked me more questions.
"Will you wear lingerie around your house and text us pictures?" He asked. "Will you wear panties to work if we ask you to?"
I was so horny and desperate to cum I would agree to just about anything right now.
behind was for me to get back underneath them and for her to ride me. My dick had been hard the whole time and when she suggested we both fuck her at the same time I felt it throb. As I slid myself down I locked eyes with Tom. He gave me a confused look as if to say 'What are you doing?' Finally I thought to myself, something they haven't planned!
I lined myself up with her pussy, but the way Tom was thrusting it was tough to get inside. For the first time in a long time Jessica used her words.
"Babe, can you stop for one second?" She asked.
Jessica leaned forward as Tom slid out of her ass a bit. She lined herself on top of my dick and slid herself down. Realizing what was happening Tom yelled.
"Holy Shit! Are you sure Babe?" Tom asked.
"Mmmm," Jessica said as she began to ride me.
Tom resumed fucking her, but not as fast. It didn't take long for the three of us to develop a rhythm. I was going deep inside of her as he was pulling out and vice versa. Jessica was panting and screaming as she had both of her holes filled at the same time for the first time in her life. I noticed her having at least two orgasms, but I have a feeling she had more. I was so turned on that I'm ashamed to say I didn't last too long after I got inside her. This was an unthinkable situation and I came hard inside my best friend again. I did my best to stay inside of her as I softened so Tom could finish. I slipped out just as he came inside her ass.
We were all exhausted and breathing heavily while we were lying on our backs.
"Guys, not to be a party pooper, but I have an early flight, so if you're both as tired as I am, I think I'll try to get a good night's sleep in my room," I said.
"Fine with me," Jessica said.
"Yeah, no problem, I have to go into work early tomorrow anyway. Jessica will take you to the airport. Thanks for coming and we'll be in touch. Hope to see you again real soon!" Tom said.
We both stood up and he gave me a Bro handshake with our fingers snapping and a quick hug. It was like we were two dude friends and it was like him fucking my brains out and us sharing his wife never happened. Except then as I started to walk away, he slapped my ass and laughed as it jiggled a bit.
"Hey," I answered.
"How's my girl doing?" He asked in a seductive voice.
"Huh?" I asked. Of course I knew what he was talking about, but I wanted to play the game.
"Oh sweetheart, are you having a case of Girl Brain?" He asked.
"I'm not sure I know why you're calling me a girl and sweetheart," I said.
"No problem, I'll remind you," he said. "While you were begging me to fuck you in the ass you agreed to wear lingerie when we asked you. You also agreed to and send us pictures just like you did on the plane. Does that ring a bell?"
"I think so," I said reluctantly, still not wanting to give in just yet.
"Don't be like that. The three of us had a great time together and this is just a way to keep those memories alive until we see you again," he said.
"Ok-ay" I said in a sing-song way.
"Great, now pick out your favorite set, put it on, take a picture and text it to us on our group chat," he said. "You have 15 minutes."
I walked over to the dresser and opened my lingerie drawer. It was still weird that not only did I have a lingerie drawer, but that a dude just called me and asked me to model it for him. I guess I was modeling it for him and his wife, but still, who was I kidding, I was totally into it.
As I was looking through my choices, a personal text from Jessica came in. "Are you ok with all of this? I know Tom can be a little bit controlling and if you don't want to do what he's asking, just forget it. I love you!"
I stared at her text for a minute before answering. "To tell you the truth I find it kinda HOT. If it gets out of control I'll let you know. I love you more!"
She replied with an emoji of a kissing face.
I focused back on the drawer. I didn't really have a 'Favorite Set', in fact I hadn't looked at anything since I put it away. I picked up the first thing I thought they'd like which was a Black D cup Bra. I found the breast inserts and the matching Black Thong. I had a pair of Black Stay-Up Stockings, so I didn't have to deal with a garter belt. That was better since I didn't have much time. I put everything on and willed my dick to stay soft. I looked at myself in the mirror and I looked ridiculous, like a guy wearing lingerie. I didn't have a wig or makeup like I did at their house, so I took a picture from my neck down. It actually looked pretty good, with my enhanced breasts and virtually hairless body. I attached it to the group text and hit send, just barely making the 15 minute time limit.
Less than 10 seconds later Tom replied, "Looking HOT Girl!"
This was followed by a picture of his hard dick. For the first time in my life I had received a dick pic.
Jessica was not far behind and texted, "Love it Sweetie!"
The she followed with a picture of her naked breasts. I had never received a naked picture from a woman either, so now they were even.
"Good girl," Tom texted, "Now here's what we want you to do. Wear lingerie all weekend. We may text you for a picture and if we do, you have 5 minutes to send us a picture. Then on Monday we want you to wear panties to work and send us two pictures 3 hours apart, one at your desk and one in the bathroom. We want you to have fun, not get in trouble. Talk soon.
I listened to what Tom had said and stayed in lingerie all weekend. I wasn't brave enough to leave the house, but I switched outfits throughout the day and sent pictures when they requested them. I was so turned on I jerked off three times each day either looking at Tom's Dick Pic or Jessica's Breasts.
Wearing panties at work was uneventful, and no one suspected anything. First I closed my office door and took a picture of the front and back of my Red Thong. Then I went into the bathroom and did the same. Both times Tom replied with a Fire emoji and Jessica just replied with a Thumbs Up, which made me laugh.
THREE MONTHS LATER
Three months had gone by with the occasional text requesting me to dress up and send pictures. What I hadn't told them was that I had expanded my collection. I had a months worth of bras and panties, plus other lingerie so I had something to sleep in every night. I didn't have the balls to go shopping in a store and Amazon had everything anyway. It took a few orders to build up my guts, but I finally decided to order a dress, makeup, and a blonde wig.
When the next text came I wanted to surprise them. Even though I was home I told them I was out and needed an hour. They agreed.
I was already wearing a bra and panties while watching TV, and I added a garter belt and stockings before taking a picture. Then I put my dress on, did a full makeup job, and styled my wig. My dress was what they call a 'Little Black Dress' that ended just above my knees. I had even bought some clip on earrings and a necklace to complete the look.
First I sent my typical lingerie picture of me from the neck down. Then before they could respond I sent the second picture which was a full body shot of me in all dolled up in my dress, jewelry, and beautiful face!
"Damn girl, we have to go clubbing when you come down!" Jessica texted.
Tom didn't reply right away which was unusual. Five minutes later I got another dick pic from him. Except this time there was a white glob of cum on the tip of his dick. Did he just jerkoff to me? That got me so turned on that I stripped off my dress and beat my dick until I came all over my panties.
The following Monday I was treated to some good news by my boss. They wanted to open up a satellite office in Florida and he wanted me to check out the area. Luckily it was the next town over from Jessica and Tom, so I already knew it was perfect. When I told them I was coming down, Tom insisted I wear full lingerie under my work clothes on the plane. That was an offer I couldn't refuse.
Jessica picked me up at the airport and had a cute sundress waiting for me when we got to the house. I stripped off my clothing and put the dress on over the lingerie I had been wearing. Tom came home about 15 minutes later and we both stood up from the couch to greet him. He totally ignored Jessica and without saying a word to me, he spun me around and bent me over the arm of the couch. He flipped up the skirt of my dress and took in the sight of my ass framed by my garters and thong. He pulled down my panties and I heard the sound of his belt buckle hitting the floor
He was balls deep inside me in an instant. Although I had been dressing at home, I hadn't played with my ass at all. I was as tight as my first time and it took some time to get used to being fucked again. Tom must have missed me, because he was jackhammering away at my hole. I looked up to see Jessica and she was smiling. Her dress was pulled up and she was fingering herself as Tom fucked me. I had a massive prostate orgasm right before Tom exploded in my ass. I was so happy to be back!
EPILOGUE
Tom, Jessica and I continued our wild sex romp while I was in Florida for work. He fucked my ass at least a dozen times and I got to have sex with Jessica multiple times too. It was sad when I had to go back home, but a month later the company decided to open that new office and I quickly volunteered to run it. They offered to help me find a place to live, but I told them I would handle it, and I moved in with Jessica and Tom permanently!
We moved the bed out of the guest room and it became my huge walk in closet and dressing area. I spent every night in their bed, which had become our bed now. I was Girl Jesse the entire time I was at home and didn't wear male clothes unless I went to work. Jessica and Tom insisted I wear panties and stockings underneath my suit pants, and we agreed it was ok to go to work without a bra. My toenails were always painted in red or pink and I would put on fake fingernails and clip on earrings when I got home as part of my changing routine.
It took some convincing, but they eventually talked me into getting B cup breast implants. They were small enough to hide under my work clothes, but they were big enough to play with and show off some cleavage in my low cut tops and dresses. 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.
I finally ventured outside all dressed up and with my new assets. Jessica and Tom surprised me at dinner with a diamond ring and a wedding band. I would wear both when I was with them and just the wedding band when I was at work. If anyone asked about the ring, at work I told them I had eloped with my best friend, which was kinda true.
Jessica came with me to all my work functions as my 'wife'. We always had a great time at these and would laugh about what she and Tom were going to do to me when we got home. It was certainly not the life I had planned back when I was in high school with Jessica, but I wouldn't trade it for anything!