Sleepover Sissy

I definitely hadn't expected Rosie to ask that. I braced myself. Hannah looked like she was going to drink, but stopped herself and said, "No."

It felt like someone punched me. I knew we weren't great in bed together, but when someone outright says it to your face, it's going to sting regardless. We'd broken up on good terms. I still liked her. Her opinion mattered to me.

I winced visibly, and felt Hannah come close to me.

"Come on," she said, "You knew you weren't that good. I'm sorry, but it's true."I couldn't look at her, as I could feel my anger and humiliation rising.

"If it makes you feel any better, I think Michelle might be better," she said, giving me a peck on the cheek.

Before I could ponder the implications, my train of thought was interrupted by Brie.

"This is boring," she said, downing her drink. "I'm spinning - and Rosie, you need to down a double. Don't think we forgot."

Rosie drank without complaint. Nobody challenged whether or not Hannah had told the truth.

It landed on Molly. "Dare me, bitch," she said, predictably.

"That's easy," Brie said. "Take your bra off."

"Hey, that's not fair!" Rosie said.

"We need a judge to decide if it's fair or not," Hannah said. "Michelle, you can be the judge!"

"Um... a dare is a dare," I replied.

Molly blew a raspberry towards Brie as she took off her bra, revealing her ample breasts and pink nipples. Seeing them definitely made me breathe harder.

Hannah noticed, and said, "They're nice tits right? Don't you wish you had them?"

I blushed in response.

Molly spun the bottle and it landed on Rosie. "You know who hasn't asked a dare?" she asked rhetorically. "Michelle."

"Fine," I replied. "Rosie, truth or dare?"

"Dare" said Rosie.

"I dare you to take off Hannah's panties."

Hannah groaned. "Ugh. I hate this part of the game, where it's just a circle jerk to see who gets naked first. Be original, you sluts." She took off her thing and threw it at me. I didn't even have time to process that my ex's pussy was completely exposed to me - to all of us. She spun the bottle, and it landed on me.

"Dare," I said preemptively.

"I dare you to finger anyone here other than Hannah," Molly said.

I gulped. It wasn't like I didn't find the girls attractive. Still, I couldn't bring myself to do it. I felt intimidated. I hesitated, and then said, "No." I drank the whole glass. Apparently, it was enough.

"Well, fair enough," Molly said. "A little too risque for her. I'm spinning!" She went after the bottle aggressively with her tits still hanging out, and they bounced and wobbled as she set it in motion. It spun for a long time, and finally landed on Rosie.

"Truth or dare, Ros?" Brie asked

"Dare," she answered.

"Oh," Brie said, as if she were surprised. "Okay... I dare you to finger Michelle for two minutes. "

I fully expected her to say something like, "No!" or "What? How? Pass."Instead, she said, "Sure. Come over here, cutie,"

I shuddered. "Um, what?"

"You heard me, Michelle!" Rosie said. "I'm going to finger you!" She beckoned me close to her.

"Um... I don't... I have never..." I tried to say.

"Shh, I got you. Rosie said. "It'll feel good, I promise. Now, sit in front of me."

I got up and realized how drunk I actually was. I stumbled a bit, then sat down in front of Rosie and felt her hold me.

She whispered in my ear, "Wanna know a secret? I've never fingered another girl either."

She ran her hands across my chest before moving her hands to my panties. They surely felt my boner, which I was sure would burst at any moment.

"Start the timer," Rosie said, but Brie refused. Rosie sighed, rolled her eyes, and then moved her fingers to the gusset of my panties. She pushed the fabric to one side so that she had access to my butthole.

"Easy, girl," she said. "Just relax."

She took her finger and started to caress my hole. She slipped inside, and I could feel myself tighten. She threw a look at Brie, who grinned, nodded, and started the timer.

Rosie's other hand was at my "boob," slowly caressing it. Her fingers reached my nipple and started to rub. Meanwhile, she pushed deeper into my hole, and I audibly gasped as I felt my body suddenly loosen. To my surprise, her finger actually felt good as she started to move it inside me slowly. My boner was straining against the fabric of my panties.

Just as I started to feel really good, and my eyes started to roll back, Molly shouted, "And that's time!"

Rosie then took her finger out of me and licked it "Mm, you are a tasty bitch, aren't you?" she said as I tried to collect my thoughts.

"Okay. Spinning again!" Molly said as she spun the bottle, once again setting her large breasts to bouncing. It landed on Brie.

"Hit me, bitch," Brie said as she took a swig of her margarita. She seemed totally unconcerned with the idea of drinking being a penalty.

"Okay, truth or dare?" Hannah asked.

"You know," Brie said, "I always say 'dare,' so I'm going to do 'truth' instead."

"Okay," Hannah said. "Would you fuck Michelle?"

"You dumb bitch!" Molly cut in. "You just wasted a question! She already said she would."

Brie laughed. "I did say that. And I gotta be honest, initially I wasn't into her at all. But seeing her butt, and the way she moves and the way she just got fingered. I would love to ravage her with my strap-on.

"All. Night. Long," she added, winking at me while I blushed. "But, since that was a freebie, I'm willing to give you another one - a dare this time."

"Dare you to strip naked, bitch," Molly said to laughter.

"Aw, come on," Hannah complained. "If she has to strip, don't make it that easy!"

"Fine," Molly said. "I dare you to convince one of us to take off your clothes for you."

"Okay," Brie replied. "This is actually going to be easier than I thought. " She got up and strutted over to me, confidently as could be. "Come on, Michelle. You know you want to see this body naked. Undress me, and I promise I'll make it worth it for you."

I lost any semblance of restraint. I just nodded while Brie helped me up. I took off her shirt, then moved to her panties and removed them as well, leaving her butt naked. Her body was as gorgeous as I had imagined: perky tits, a perfect butt, and thighs that could crush me. I was about to go sit back down, but she took my hand.

"Here's a small gift for you," Brie said. "Why don't you give my boobs a squeeze? They're not much, but you'll love the way they feel in your mouth, too. Come on and give 'em a kiss too."

I felt my mouth go to her boobs and slowly kiss her nipples, as if it belonged to someone else. My eyes wandered to her, as if asking for approval, but she didn't say anything. I started to suck on it slowly. It must not have been long, and I swear I heard Brie moan, but Hannah said, "That's enough! Leave some for the rest of us!"

Brie then winked at me and sat down. I did too. I felt unsteady from the alcohol, but also like I was floating on a cloud. I wasn't sure how I hadn't exploded in my panties yet.

"Okay," Hannah continued, as she fetched us even more margaritas. "Things are definitely heating up. I have lost count of who's spinning who's not."

"I can spin," I volunteered, "although I don't know how long. I'm pretty drunk." I giggled, just like a girl.

"Go ahead, sweetie," Rosie said. "This is nothing. We've got a ways to go if last time was any indication."

"What happened last time?" I asked.

"Well, things got wild," Rosie answered. "Molly's boyfriend and a friend showed up, and Hannah wouldn't stop sucking that dude's dick."

My eyes grew wide.

"Relax," Hannah said. "It was after we broke up - and, in my defense, his dick was beautiful."

I felt a pang in my heart hearing my ex-girlfriend describe another man's penis.

"Now, I thought you were spinning?" Hannah asked.

I nodded and spun the bottle. It landed on Molly.

"Molly, I can't be the only naked one here," Brie said. "I dare you to take off your panties."

"Boooo!" Rosie exclaimed immediately. "Come up with something original, why don't you?"

"I have one," Brie replied. "I dare you to take off your panties and eat Michelle's ass for five minutes."

"Oooh, I like this," Molly said as she threw her panties away and beckoned to me.

I couldn't stop giggling as I crawled over to her. She took me in her arms and kissed me. I felt like I could cum any moment.

"Take those off and bend over for me," she said, and I complied, too drunk to argue.

I got on all fours, and Molly didn't wait for me; she peeled off my panties for me, and gave my cheeks a kiss before spreading them and using her tongue on me. The first second it felt weird, but as her tongue started to work her way into my hole, it felt good. My eyes rolled into the back of my head, and I started moaning again.

"Fuck, that's so hot," Brie said in the corner to Rosie sitting next to her "I wish I could go next." She started rubbing herself.

"I've never really been eaten before," Rosie admitted, blushing. " It... uh... looks fun."

"Well Ros, I'd love to give you a spin if you don't mind," Brie said, offering her hand.

"Sure," Rosie replied, taking Brie's hand and lifting herself off the floor before taking off the remainder of her clothes and joining me on all fours. Brie crawled behind her and started eating her ass. It must have been quite a sight: the four of us, almost naked, eating each other out.

Meanwhile, I was close to cumming. "Molly. Fuck. Don't stop" I yelled while my eyes rolled.

"No!"Hannah shouted. "Stop! I have an idea. Brie? Do you still have your 'you-know' on you?

Brie nodded, and Hannah ran to get this thing, whatever it was.

Meanwhile, Molly had stopped eating me and caught her breath. "Michelle," she asked, "do you want to return the favor and maybe eat my puss?" She got on her back and spread her legs, confident what my answer would be.I nodded and started eating her out. Then I felt someone behind me. As Brie and Rosie were on all fours next to us, I assumed it was Hannah. "You know, I've waited a long time for this, Michelle," she said. "Fuck off Molly, she all mine."

"Aww it was just getting good," Molly complained, but she let me withdraw, then started to rub herself.

I felt Hannah put something cool on my hole. "I have wanted to fuck you for so long," she said. "Now you'll know what it's like to be fucked - not that lacklustre performance Mike used to give."

I felt my butthole being split by something. I realized it was a strapon. I moaned. "Fuck," I managed to say while Hannah slipped in.

"'Fuck' is right," Molly said. "This is so hot." Molly said as Rose brought her closer.

Molly, Rosie and Brie were in a threesome, with Rosie in the middle, eating out Molly, while Brie snacked on her ass in turn. Moans from multiple girls filled the room.. My own situation was getting very intense. With every thrust, Hannah had started spanking me, saying things like, "You like that, don't you? You dirty whore. You love me fucking you like this. You missed me, didn't you?"

"Yes yes yes," I started moaning as I got closer to climax. I started stroking myself, or tried to, until Hannah slapped my hand away

"No. Good girls don't touch themselves like that," she said in between thrusts.

I couldn't take it anymore and started to cum, moaning out, "Hannah, I'm coming."

In one swift motion, Hannah pulled her hand out, collected my cum, and forced it through my mouth.

"Good girls swallow," Hannah said as she continued to thrust despite my orgasm having already arrived. In between thrusts, I managed to swallow my own juices. They tasted fine, as salty as I'd imagine it to taste. As Hannah continued to thrust, I laid out my tongue for everyone to see as if indicating I swallowed all my cum. A momentous occasion, that I have come to regard as the moment my repressed inner sissy slut was released for the first time.

Seeing me drink my own cum certainly seemed to bring Molly over the edge. Her moans reached a crescendo, and she laid back down in exhaustion.

Hannah, meanwhile, seemed to be moaning louder and louder until she stopped with one final thrust. She then removed her strapon from me, and joined Molly on the floor. I sank down, rolled over, and then snuggled up to my ex. She cuddled me.

"Was that good for you, baby?" she asked."Fucking amazing," I replied as the room began to quiet down.

I realized that I really liked being Michelle, and I had a feeling I wasn't done being her yet.