It was a Tuesday night, and Bill was in town for the week. On this evening I knew something was up, I had an inkling we were going to have someone join us that evening; yet, I wasn’t 100% sure. You never can be with Bill.
Tuesday morning when Bill was getting ready for work, I was lying in bed watching him get dressed – something I adore. Watching him put on his work clothes, knowing all the filthy and inappropriate things we get up to once I take them off at night, drives me absolutely wild.
While he was buttoning his shirt, he turned and looked at me, then sat down on the bed next to me, stroking my leg over the sheet.
“Wear some sexy lingerie tonight,” he said giving my leg a squeeze and returning to his shirt. My interest was piqued.
“Don’t I always,” I replied coyly.
It was true. Every girl has their weakness and bras and panties are mine. Just writing this I’m thinking about the next set I could buy at my favorite boutique – they know me by name! (Side note from the time I started this to the time I finished this I purchased two new sets, your girl has an addiction!)
“I know, baby. I just want to make sure… and wear something sexy too,” he gave my ass I quick slap and got up to finish getting dressed.
Now I was genuinely perplexed and intrigued. Bill’s seen all my lingerie (we’ve been together for almost 4 months), the only reason I’d need to wear something special was if someone else was going to see it. He’d been talking about a friend of his, Jackson, for a month or two. They’d had a threesome together before, and he had asked if I was interested in trying one with Jackson.
I’d never had a Male/Male/ Female threesome before, just one with another girl two or three years ago. I was pretty inebriated and don’t remember much. I can’t honestly say how much of an active participant I was in that process. I was game for it, and after seeing a picture of Jackson, I told Bill I was interested, assuming there was some chemistry when I met him in person. Jackson had a cute face, a brunette. He was built well, with strong arms. He was in his mid to late 20s, not my type per say, but under the circumstances, I thought he’d be an excellent foil to Bill.
That night I got to Bill’s place wearing a set of black panties and a matching bra with see-through cups, and a bodycon dress with mesh at the waist and the hem. I usually would contrast what lingerie I wear with my clothes, but for this evening I had my heart set on each of those pieces, so all black it was! I arrived at Bill’s with my gym bag, which held a pair of red heels (I had to get red in there somewhere), my gym clothes and purse.
Bill and I had done the most coupley thing that week I could think of: joined a gym together. We have yet to go at the same time, but I thoroughly look forward to low key following him around the gym and watching him lift weights. I know it will take all my willpower not to straddle him on a bench press and take him right there. Just writing this is getting me very distracted and excited!
“You look incredible” was the first thing he said to me as I walked in the door.
He pulled me toward him for a kiss then pushed me up against the door as it closed behind me. His hands ran along all the mesh parts of my dress, at my waist and at the hem of my skirt. His mouth moved along my jawline and down my neck then back up to my ear.
“Why are you so beautiful?” he asked nipping at my ear, literally causing me to shake.
I had no reply. I’m horrible at accepting compliments (and have been told so by many men), and I also couldn’t get my brain to work while Bill was doing that to my ear. All I could do was moan and buck my hips toward him as he continued to tease me. After what was far too little time in my estimation he pulled away from me, giving me one last peck on the cheek.
“We have to be somewhere in 15 minutes, are you all ready to go? Do you need anything out of that adorable little purse you brought?” he said walking into the bedroom to put on his shoes.
“Purse?” I scoffed following him. “That thing is enormous, and it’s my gym bag! I’m sorry some people actually carry gym clothes in their gym bags, not sex toys like you, you deviant,” with that I straddled him.
I started kissing him softly at first, pulling back every time he attempted to deepen the kiss. After only a minute or two I finally grabbed the back of his head and pulled him toward me, intertwining his tongue with mine, tasting every inch of his mouth. After a few minutes of this, he pulled away from me, stroking my hair and looked me up and down.
“Baby first, all your purses are big. Your gym bag is adorable, just like you” he said kissing my forehead. “Secondly, if we don’t stop now, I’m going to tear that dress off and do very inappropriate things to your body, and while I would love that, it would ruin the surprise of this evening. You know once I start to make love to you, I can’t stop.”
At that, he stood up with me still straddling him. I wrapped my legs around him so I wouldn’t fall. I snaked my arms around his neck, and he put his hands under my ass, squeezing it then lifting me up, so I was in a more secure position. He started kissing me again and walking toward the living room. When he got near the front door, he pushed me against the wall, gyrating his hips into mine. I could feel the length of him pressed up against me, and I wanted nothing more than to take off these goddamn panties and have him take me right against this wall. After a minute of this and with an audible growl he put me down.
“Alright young lady, are you ready to leave?” he asked, all business as if we were talking about heading out to a conference. I sighed in frustration at the loss of contact but bucked up when I recalled that I had no idea what we were doing tonight.
“Heels or no heels?” I asked sticking my leg and grey flats out.
“Whatever you prefer, your legs look amazing in each. Doesn’t matter to me, it’s whatever you are comfortable in,” Bill said sweetly.
Bill has a thing for calves, it’s his favorite place on a women’s body (well second favorite). According to Bill, your genetics determine if you have good calves or not, you can work out to build them up, but if you aren’t predisposed to it, then you’ll never have amazing calves. Not something I’ve independently researched.
“Well is it far? Will I be upset if I show up without heels on? How fancy is this place? I know you are coy, but you have to give a girl something to work off of.
“It’s a 15-minute walk,” he said quickly before I could ask more questions.
“O bugger, then flats it is,” he laughed at that.
I grabbed my purse, and we headed down the 8 flights of stairs (this was the worst Air BnB he had stayed in with me) and out onto the street. He pulled out his phone and started to navigate us, stopping at the first intersection to ask me which way I thought a particular road was. We walked for 2 or three minutes, and then he stopped abruptly in front of a bar.
“We’re here,” he said pulling me toward him and giving me a quick kiss before walking in holding my hand.
The bar was nondescript, a little nicer than a pub, but nothing fancy. He walked toward the bar where I assumed we’d be sitting, it’s where we always sit. Then just before he got to the bar he stopped turned around and shook hands with a guy sitting at a four-top table alone.
“Hey man, how is it going?” Bill asked giving the young guy’s hand a firm shake.
“Good, man. You?” the young man replied. He was brunette and looked to be in his mid to late twenties. Bill turned to me.
“This is ***. **** this is Jackson.” Bill turned from Jackson to me with a shit eating grin on his face.
So this was finally happening. I had seen Jackson’s picture two months beforehand, but not sense. Which is is why I didn’t recognize him. Jackson looked like his pictures, and his presence there confirmed my suspicions. MY surprise tonight was a threesome.
“Oooo, Jackson,” I said with a smile shaking his hand. “It’s good to finally meet you.”
I moved around the table to sit next to Bill, but he put his hand on my waist and stopped me.
“No way darling, you sit here,” he moved me back to the head of the table, in between the two men. I sat down, and we all began to chat. Jackson was an architect and had played soccer in college. He was moderately interesting. We both missed the movies Bill referenced and enjoyed giving him shit for not getting things like a quote from Mean Girls. After one drink, for the men, Jackson got up to get us another round.
“What do you think baby?” Bill asked, leaning int toward me, covering my hand with his and giving me a quick kiss.
“Jackson seems very nice,” I said shyly. I wasn’t sure exactly how to respond in this situation, just how much Bill was ok or wanted me to be attracted to Jackson. It’s all new territory, so I trod lightly.
“Do you want him to come home with us?” he asked, stroking my hand and looking at me intently.
“Yes,” was all I could get out, squeezing his hand. I leaned in and gave him a deep, sensuous kiss.
I was nervous and excited, my kiss said all of this. Bill put his hand around the back of my head and pulled me forward, deepening it and reassuring me that I had nothing to worry about, but also reminding me that he’d be there for everything. It only increased my anticipation.
I flirted with Jackson more during our next drink, it may have been Bill’s reassurance or the whiskey, but I was more confident. I touched his hand or his shoulder when we spoke, made comments a little more suggestive than I had before. We finished our drinks quickly and headed back to Bill’s, Jackon didn’t even ask where we were going, merely followed us. They’d clearly discussed all of this beforehand.
Once at Bill’s I immediately took my shoes off in the living room. They had fallen off once on the stairs and were really annoying me.
“It’s hot as hell in here, this is the only cool place in the whole apartment,” Bill said as he opened the door to the bedroom and strolled in.
It was true, the apartment had claimed to have “A/C” on the Air BnB advertisement that we had looked at a few weeks before when he was booking, but it only had a window air unit in the bedroom. It had been in the mid 90’s all week and humid. I was okay, but Bill was annoyed as they did not have this kind of humidity in Colorado.
Jackson pulled off his shoes in the living room, like me, then followed Bill in and plopped down on the bed (which I had made that morning). Bill was sitting in a chair by the window taking off his shoes, facing the bed. I made my way toward the bed, intending to go around to the other side and maybe lay down on the opposite side of the bed. I honestly had no idea what the protocol was at this point in the evening, the beginning. Who was I supposed to start with? What was acceptable? Bill keeps saying he isn’t the jealous type, but I’ve seen moments of it creep in, and I did not want to do anything to upset him here.
As I made my way toward the edge of the bed where Jackson was, he grabbed my hand and in one swift motion pulled me top of him. I gasped in surprise and arousal. Clearly, the first move was on Jackson, this was his opening gambit.
I was straddling him, he had one hand grabbing my ass and another running through my hair. His lips grazed my neck for just a moment before he pulled my head back by the hair ever so slightly and brought my mouth to meet him for a kiss. In that exact moment, I forgot Bill was in the room, I merely felt the excitement of kissing someone for the first time. He was a decent kisser, but a young one, all fervor, and vigor, little appreciation for the slow and sensual art of taking your time. Don’t get me wrong, I like things to be fast and passionate, but you also have to know how to change up your pace to keep it interesting – any men who want advice on this should message me!
Still, I enjoyed it. Our tongues collided, fighting for dominance. Jackson bit on my lower lip, making me moan into his mouth. His hands were continually roaving across my body. After just two or three minutes of this, I felt a weight on the bed and realized it was Bill. My body tensed for about a five second before I realized that if he’d had a problem with how things were going, they wouldn’t have progressed for this long. I felt him behind me, his breath on my neck and his hands at the zipper of my dress, slowly pulling it down and pulling the dress off my shoulders.
“Someone is wearing too many clothes” he whispered in my ear, giving it a quick bite before my dress was unzipped entirely and off my shoulders.
I groaned at this, his words in my ear and Jackson’s lips on mine. I was already in a state. He started to pull the dress up over my head, and I broke my kiss with Jackson. Once it was off, Jackson didn’t return to kissing me, but looked over my body hungrily, focusing on my breasts.
“Fuck, that bra,” he said almost under his breath, noticing my sheer black bra with velvet trim. You could see my entire breast through it. It was like looking at a candy bar through a see-through wrapper.
I felt like the bra deserved a visual
His hands moved up to cup my breasts, and after just a few seconds his mouth returned to mine. I felt Bill move from behind me, off the bed.
“I’m going to get you both some water,” he said making his way toward the door and the kitchen. I broke my kiss to look up at him.
“Thanks, Dad,” I said cheekily with a grin. Daddy is something I call Bill very often, but I knew to call him Dad would amuse and annoy him. Jackson laughed.
“Someone is going to be punished later for her smart mouth, isn’t she?” he said kiddingly, with a hint of bite. He walked over and gave my ass one very hard slap before walking toward the kitchen.
“You two keep at it,” Bill said before walking out.
That seemed as good as any license to continue to get back to things with Jackson. I grabbed him by the back of the head and pulled him toward me. I licked his lower lip, pulling away every time he tried to kiss me. I teased him with my lips and tongue, showing him that a little anticipation can be a good thing. Maybe that was my way of paying it forward that night. Perhaps I helped out some future twenty-something girl.
Next thing I knew I heard a thud on the bedside table. Bill had put down two glasses of ice water.
“Thanks, Daddy,” I said, emphasizing the Daddy portion of my comment. I wasn’t sure how much of a spanking I was up for after we got through with this whole…. interaction.
I took a sip of water, as did Jackson. I was still straddling him. Even though my dress had been taken off, I was still in the same position I had been when he first pulled me down on the bed, but for some reason, I was the only one-half naked while the men were all fully clothed.
“Something is terribly wrong here,” I said huskily, but a bit more dramatically than I intended.
“Baby, what’s wrong?” Bill rushed over to the bed behind me and started rubbing my shoulder.
“It’s just that both of you are wearing far too many clothes. It’s not equal, it’s not very feminist of me, now is it?” I said looking at Bill and giving him a quick kiss and a smile. He and Jackson both started laughing.
“Fair enough,” Bill said and started to take off his shirt.
I turned to Jackson and started to pull his shirt up over his head after he’d given me a look that had said ‘you take this off.’ Don’t ask me exactly what that look is, you just know it when you see it.
“I think that means you need to be wearing even less if we are going to keep on this equal path,” Jackson said, reaching around behind me to undo my bra.
Once it was off, Jackson flipped me onto the bed. He took one nipple in his mouth, sucking, licking, biting. Then moved onto the other nipple. Once satisfied he moved back to kiss me, his hands moving between my legs, touching me through my sheer panties. I moaned in pleasure, arching my back. After a minute of this, he was pulling off my panties and had one finger inside me. The moment his finger first entered me my breath hitched, and I moaned even louder.
“You are so tight and so wet,” Jackson said half to me and half to Bill.
I looked over at Bill who was sitting on the chair by the window, facing the bed watching us and stroking his cock. God, I wanted to feel him inside me. I wanted to taste that cock, have him fill me up, but then I remembered that Jackson was on top of me and I had two cocks to handle tonight.
Consider that the foreplay, my friends. Like all good sex sessions, a little anticipation only makes it feel better. Hope you enjoyed this first part. Please leave a comment, questions, or suggestion below! Don’t forget to follow, so you know precisely when the newest posts are up!
Up To No Good 😉