New Year’s Resolution Get pegged!

I was in grad school, and after we finished high school and college my friends and I, mostly based in the area around Connecticut and Westchester, New York had dispersed to various corners of the country and it was getting increasingly hard to make plans with everyone being on different schedules.

I had one friend, though, Marcia, who was quite the social butterfly. Marcia could fit in nearly anywhere, she was a party girl, but also classy. She was a bit of a geek, but dressed and acted like a popular girl just as easily. Marcia could fit in anywhere and knew it.

She could go straight from work or school to a game of Dungeons & Dragons then to a club, and if she wanted to, she could come home with a partner and show up at brunch the next day looking as wholesome or trashy as she wanted.

She could be rowdy at a sporting event and classy at a nice restaurant. She could be competitive, but also helpful. Marcia was bisexual, and attracted as much to guys as to girls. That made it even easier.

Marcia was a curvy girl who carried herself with a certain elegance, she always was well dressed and she was quite attractive, she had brown hair with blonde highlights well positioned throughout. Despite being a bit overweight, Marcia was a very pretty girl and offset that with her irresistible charm and self-confidence.

I wasn’t like Marcia; I was kind of socially awkward and straight up nerdy. Although Marcia had been trying to get me to loosen up a bit. That New Year’s Eve Marcia discovered the day before that I simply did not have plans, and might even turn in early. Not having many other options, I agreed. Marcia’s parents were loaded and set her up with a nice apartment in New York City. It was a short train ride from where I lived in Norwalk.

Being organized, I left early, and avoided the mayhem of New York during New Year’s Eve. The tourists, the police, the convoluted mass transit, and the presence of federal agents and soldiers was close to overwhelming. When I arrived at Marcia’s apartment, I was impressed by how spacious it was. Upon arriving Marcia gave me a big hug and I met her friends, aside from Marcia and I there seven people there, four girls and three guys.

I mostly initially socialized with Marcia, I wasn’t quite the butterfly she was, and Marcia had dressed up trendier and more feminine for that night, she wore a dress of a sort of loose fabric and did what she could to expose her cleavage. As nice as Marcia looked, she had one friend who caught my eye early on. She had a cute face and dark hair that she wore shorter than the other girls, only descending down to the middle of her neck. She was slender and was wearing a tight white top and a tight short black skirt. She had heels on as well, they looked to be about three inches.

I found out her name was Dana and when I went into the kitchen to help Marcia with something Dana suddenly entered to get more ice and Marcia said, “hey Dana, how was that party the other day, I’m sorry I couldn’t make it!”

“Oh, it was fun it got pretty crazy after we all got drunk,” said Dana.

“Tell me the juicy details!” said Marcia.

“Well for starters, I pegged a guy! It was awesome, I really feel like every guy should get pegged at least once,” said Dana excitedly. Marcia and Dana shared a laugh.

I simply listened and found myself nervous and aroused and said “why is that?”

Dana looked at me and said, “I think it’s a great equalizer and lets guys know what they expect girls to do for them.”

Marcia knew how submissive and kinky I was, even though I usually came off as somewhat uptight. She also knew I lamented how hard it was to find a pretty girl who wanted to dominate me. Marcia said to me, “so what did you think about Dana?”

“Well, she’s quite a character, very cute,” I said nervously.

“What do you think about her theory?” asked Marcia.

“I don’t know,” I said, I was getting uncomfortable.

“I think you want her to peg you, I did promise to broaden your horizons…” said Marcia.

“Hey Dana!” Marcia shouted.

“Marcia, No!” I said.

Dana came back into the kitchen, “what’s up?”

“He wants to tell you something,” said Marcia.

“What?” asked Dana.

“Come on,” said Marcia.

“Remember how you said every guy deserves to be pegged at least once, I’m a guy,” I said to Dana quickly and quietly.

Dana laughed then smiled at me with a feminist impudence, “I’d love to peg you, but I don’t have my stuff with me.”

“You can borrow mine, I keep it clean,” said Marcia.

“Thanks,” said Dana, so Marcia lead Dana and I into her spare bedroom and handed her a pink strap-on and harness. Dana went into the bathroom to get ready and Marcia produced a pink rope and brought me into her spare bedroom and tied my arms and upper torso to the bed facedown.

“Marcia, what are the other guests going to think?” I asked,

“Nothing at all,” said Marcia, “People step out during parties all the time.”

“Aren’t you glad you came?” asked Marcia, putting lube and paper towels down, “I promise, you’re in capable hands!” Marcia’s spare bed was several inches from the wall and she slid her floor mirror so it was in front of me. I could see myself. Marcia then removed my pants and underwear. I protested, she responded, “Look, Dana will have to see you butt anyway to do this. If she can see your dick, that’s good, you’re already hard, if you stay that way she’ll know you’re having a good time.”

Dana finally exited the bathroom finally and walked up to me, she removed her skirt and revealed the strap on. “Ready to be my bitch?” asked Dana seductively.

I could only really groan a bit, I was extremely nervous and felt vulnerable, but aroused.

Dana went into Michelle’s dresser and took out a very short pick skirt. Marcia, who was stronger than me held me down while Dana put it on me. I said “Dana, no!”

Dana said, “he talks too much, Marcia handed her a ball gag and Dana slammed it into my mouth tightening the straps behind me. The girls then bound my lower body to the bed. They giggled as my shouting was muffled by the gag.

Dana acquired some baby wipes and took diligence to clean my anal cavity. “Your shit getting all over the place is going to be nasty, there will be a little regardless, boy, but this will be good.”

Dana said to me, “I’m disappointed to put the ball gag in you, that way you can’t beg for me to fuck you, Oh well.” I saw the small dark-haired cutie pump the lube onto her hands before seeing her rub down the strap-on from the mirror. She then said “ready or not, here I come!”

It was first awkward, then uncomfortable, the painful, but still extremely arousing. I could tell she had experience with making a man feel all these same feelings before. “Yeah, that’s right boy! How’s it feel to get fucked by a girl? How’s it feel to have your ass cherry popped? You like being my bitch? Your dick sure says so! How many girls have you fucked before?

How many bodies has that little thing invaded.” I loved her words, they made me feel so inferior to her. I simply was glad she didn’t know the truth, the answer was zero. I was a constant strike-out in high school, college, and now in post-college life. I had girl friends in the past, but for a variety of reasons we never really got past second base.

Once again Marcia threw Dana a bone, “Dana, I know how many, zero!”

“You’re a virgin?” said Dana astonished, she started to laugh and quicken her pace, so you lost it here tonight to a girl penetrating your ass! That’s awesome!” Dana began slapping my ass and Marcia began fingering herself. All three of us were moaning, Dana was getting turned on by the experience as was I, and we were adequate fodder for Marcia’s masturbatory experience. I never felt so violated and turned on.

“Oh fuck yeah!” Dana said.

“That’s it, come on Dana, punish his little asshole,” said Marcia.

“Come on you little bitch, you wanna cum for me?” said Dana, “you’re my little bitch. You are such a good little slut for this!”

In my head, it’s easy to be “a good little slut” when you can’t move. That said, watching Dana pounding my arse in the mirror was so sexy and my love for it proved I didn’t need restraints to be a good slut!

I was moaning through the gag, my entire world was my butt and my prostate and Dana slapping my butt while penetrating my anus. Finally Dana’s hand took a break from slapping me to stroking my penis. I blew my load almost immediately after in the most powerful orgasm of my entire life.

Dana did not stop immediately, she still had a bit more to go and finally pretty much laid down on the floor panting. Marcia removed the ball gag. But we all sat in silence, Dana on the floor with her strap on still on, Marcia on the foot of the double-bed, and me, tied down buttocks still up, still in that micro skirt the girls thought was funny to put on.

At this moment we were all in bliss. Dana from pure female empowerment, me from submission and orgasm, and Marcia from a bit of both. My ass was sore and tingling, but I loved it.

Dana finally asked, “did you enjoy me making you cum?”

“Yes, Dana,” I said.

“My turn!” said Dana and she removed the gag and sat on my face. I shrieked in surprise a bit but it was lost in her butt. She moved around a bit until her pussy was on my mouth, “now, bitch, eat me out.

Dana grinded on my face as I tried to keep my inexperience tongue inside her. But Dana began moaning when I found the g-spot and enjoyed the activity.

I lapped with all my might, planning my breathing to when I had an opening with my nose, as my mouth was far too busy. Dana was my goddess and her pleasure was my priority. Eventually Dana came. My face was covered in her female juices and I was tied up an unable to get it done,

“How about you, Marcia?” asked Dana, “I think our little fucktoy can handle a little more. I think she may have heard me groan in some way, because she continued. “Yeah, that’s right, bitch, you’re our fucktoy! Just a plaything of two girls who are superior to you in every way!”

“Why not?” said Marcia, “I already orgasmed, but I can have another. Marcia promptly mounted my face. I was okay with being sexually dominated by Dana, but Marcia and I had been friends for so long, and while I can’t deny I found her attractive all this time, I wasn’t sure if I wanted to have a sexual encounter with her.

I looked up at my soon-to-be sexual conqueror and she looked down at me with a triumphant smirk. Then she began to grind against my face as my tongue darted inside her already wet pussy. As Marcia moaned, Dana began playing with my cock and balls, stroking and fondling them. I was already churning again despite by earlier orgasm.

Dana then suddenly gave my balls a squeeze and pain rippled through them. Apparently as I spasmed, my tongue moved about in a way Marcia found very pleasurable, as she moaned intensely. She then said “Oh, More, more, just like that!” Dana looked into the mirror and winked at me flirtatiously. She continued the fondling until she gave me the same squeeze again.

Fortunately my tongue that time made Marcia climax and she added her feminine justices to Dana’s on my already abused face. As Marcia dismounted and redressed the two girls were smiling. I hated to admit it, but despite the pain I was too.

The girls untied me finally and Dana kissed me passionately and told me she had a great time and we should do it again. I said “thank you, Dana, I would love to.”

Marcia said to me, “You were so shy, but I know you loved every minute of it!” She was right, I wanted it all. I would happily please her again too.”

I was given my pants back and returned the soaked skirt to Marcia who held it like a turd and tossed it in the hamper. The girls and I all washed up before coming back outside. When the ball dropped not long after, Dana grabbed me and gave me a passionate and aggressive kiss, forcing her tongue deep into my mouth.

Marcia encouraged Dana and I to spend the night, which we both accepted. Dana took the guest bed, which really wasn’t big enough for both of us, so I took the couch. Dana and I made out before going to bed.

I was disappointed I didn’t get more action, but shortly after Marcia had fallen asleep Dana snuck up to me in the couch and pulled my boxers to my ankles and sensually slid my penis into her mouth. She sucked it intensely and wrapped her tongue around it.

She had deepthroated it like a professional and within seconds I had exploded into her mouth. Dana, mouth full of cum swished it around a bit before spitting it out onto my face.

She laughed and said, “that’s three people’s cum on your face in one night, you’re such a slut!” She then gave me a damp wascloth while laughing softly.

Even with cum in my face, I had just gotten a blow job from a beautiful girl who knew what she was doing, I was in heaven, even if I was being totally dominated the whole way.

When I woke up, I was greeted by both girls smiling and laughing, Marcia was holding a leash and a collar and they both removed my baggy t-shirt and boxer briefs and put the collar on me.

“You’re our bitch now!” said Dana. “I know you love it!” said Marcia. I was a bit shocked. The girls were laughing. Marcia began dragging me along on the leash. I was sporting a huge erection. Marcia was right. I craved to be a slave to these two cuties. The uptight man I was yesterday had died and the willing slave to these two girls would rise from his ashes like a phoenix.

My experiences as a slave the following day, however, are another adventure.

To be continued.

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