Two Skirts are Better than One

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
88girfriend
88girfriend
199 Followers

Harmony smiled and I figured out in an instant he had been kidding. I slapped him on the ass to punish him and if anything, his smile got bigger. If his intent had been to bait me then mission accomplished because I was not afraid anymore. I was pissed. I walked over spread his cheeks and shoved my cock home.

"Not so rough," Harmony said in a mock whine.

I pulled back and Harmony grabbed my bra and pulled me closer so that my dick went deeper into him. He pushed me back and then pulled me forward again. After this quick tutorial on how to properly fuck your lover's ass Harmony left me to practice. Apparently, I was a fast learner and before long he was letting out a series of grunts and moans. I added even more lube to my dick from time to time but kept going. "That's it, Aaron," Harmony cooed, "Harder though, please."

I had only had sex a couple of times before and it had not been fun at all. It had been clumsy and awkward. In both cases, I am pretty sure the girls were as inexperienced as me so there was a lot of fumbling and I think I must have asked, "Oh, is that alright?" or "does that hurt?" at least a dozen times.

With Harmony, it was like we were in sync. We didn't have to talk. He put his legs on my shoulders and I smiled telling him that was OK. I stood on my tippy toes so that I put more weight on his pelvis and he closed his eyes telling me that was a great idea. Later, I rubbed my cheek against his stocking-covered foot and he raised his eyebrows. The simple gesture said to me, "Oh you're one of those foot guys. Good, because so am I."

With his hands now free, Harmony started stroking his cock. I had watched many porn videos in which a man started stroking his dick. I have to admit it had always given me more than a little erotic boost to see this happen. That of course was nothing compared to the pleasure I was currently feeling from watching Harmony play with himself, knowing full well that my dick being up his ass and him looking at me were the two main reasons he felt the need to jack off.

"You like me fucking your boy pussy baby?" I asked a little winded.

"I love you fucking me, Aaron."

"Good, because I love fucking you." I said then took a breath, "Your ass is eating my pole and it feels so ffffuuuuckking good."

"I've always wanted you, Aaron." Harmony began to confess, "I used to follow you around all the time because I wanted you to like me. I needed you to like me because I lived to be near you and please you. Then we all got sent to work remotely and I died. Thank goodness I found you on chat or I don't know what I would have done."

Harmony's admonishing didn't just inflate my ego it also inflated my cock a little. I started pressing deeper into his hole. Neither of us was what you would call physically fit. I could see the beads of sweat forming everywhere on Harmony's exposed skin. He was breathing hard and I felt like I was back in gym class running a mile.

Thankfully, I had left the bottle of lube on the bed. I sprinkled some lube on Harmony's cock as it looked a little dry. Harmony said thank you by smiling up at me and stroking his cock faster. I never realized how erotic that squelching sound that lube makes was before now. Harmony gritted his teeth and I could see him straining. I too was on verge of climax and was not sure how much longer I could hold it.

My leg muscles began to beg me to stop. My back started to tighten under the weight of Harmony's legs. "I've got to cum Harmony," I whined.

"Then cum Aaron," Harmony grunted, "fill my ass and make me yours."

My balls had been growing more and more uncomfortable as time went by. I could feel them swinging like two kiwis in a sock the entire time but now they were hard as a rock. I felt a pull on them as though someone had hooked an extra gram or two of weight to them. With Harmony's permission now given, I looked down at my new sissy boyfriend and exploded.

I am pretty sure I stopped breathing. My leg muscles locked and I just stood there with my hose as deep in his ass as I could manage. I am sure that I only ejaculated for a few seconds, but it felt like I was watering the lawn. I pumped ounce after ounce into his behind.

At some point, while delivering my payload, Harmony also crested. His dick became a fountain of cum. One solid stream shot as far up as his belly button and then several smaller globs hit him just below the waistline. Bomb run complete I pulled out and fell on the floor fatigued and trying to catch my breath.

Harmony equally exhausted had simply let his legs fall to the ground and was even now laying there like a landed halibut. Several minutes later I was treated to the extremely sexy site of my cum flowing out of Harmony's ass like a little volcano and all over my sheets. It was almost enough to get me hard again.

When I could feel my legs again, I crept slowly up onto the bed. I was slightly winded again by the time I collapsed next to Harmony. At some point, he had crawled back up onto the bed leaving a thin trail of cum in his wake.

I wanted to put my arms around him and start kissing his chest but I just didn't have the strength. I ended up on my stomach, arms beneath me, and my head turned towards him. His eyes were closed and his breathing was pretty regular. "I so need to get to the gym," I said to no one in particular.

"Yep." Harmony said then turned to me and smiled, "lots of hot guys at the gym."

We both laughed and then just laid on the bed for about twenty minutes taking a power nap.

"So, what do we do now?" Harmony asked.

I rolled over and stared at my ceiling. "Now we get up, get naked and get into a shower."

"OK."

"Then we both put on some very nice woman's pajamas and I will order pizza." I went on.

"I like what I am hearing so far." Harmony turned towards me and propped himself up on one elbow.

"We put Star Blazer in and watch it while we eat the pizza," I finished.

"What about the delivery guy?" Harmony asked.

"He can join us," I smiled, "but only if he brings his own pie. I'm not sharing ours. I'm hungry."

"Sex will do that to a person," Harmony said and moved closer. "I meant what if he sees us dressed as girls?"

"Maybe he will think I'm Aaron's girlfriend." I smiled back at Harmony, "You did."

It took us an hour but my plan was going great. We had both gotten cleaned up. I gave Harmony a short sleeve pajama shirt that buttoned up the front with matching boy shorts. I dressed in a set that was almost identical the only difference being that my set was mint green and his were salmon pink. Turns out salmon is Harmony's favorite color.

I went down to get the pizza. I don't know if the guy thought I was Aaron's girlfriend but he obviously thought I had a nice ass. He looked me over several times while I looked over the receipt. I also saw in the reflection of the elevator doors that he had watched my ass as I walked back to the elevator. Harmony had given me a walking lesson on how to walk while we waited for the pizza.

I was on cloud nine as I reached my floor. I had not seen a single person other than the delivery guy and I was home free. I was humming I've Got the World on a String as I came to my door. I knocked twice to get Harmony to open the door. The door opened and Harmony appeared. Then his eyes widened in terror. The door behind me opened and Sophy walked into the hall with her friend Kendra Kline. Harmony and I froze.

"Hey, Aaron. Nice PJs." Sophy said and started down the hall with her friend.

"I have a pair just like those in green," Kendra added. "They are so comfy."

Harmony stuck his head out the door and watched the two girls walk down the hall. The elevator doors closed, and I walked in and set the pizza box on the table. "Do you think they'll tell?" asked Harmony as he closed the door and joined me at the table.

"I don't know," I answered him honestly.

Thank you so much for reading. If you liked this story, you may also like my Becoming Miss Cooper series or the Photo Foreplay series. Thanks again and don't forget to vote and comment.

88girfriend
88girfriend
199 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
dreamer31adreamer31aabout 1 year ago

wish i had a bf like that thanks

ClitNinjaClitNinjaabout 1 year ago

Hi 88girlfriend... I just finished reading this story. There is so much I like about this story. I will start with why we read most Literotica stories. And my why was answered - I was aroused thru the entire read. Today is Saturday and I had to work ( 8-2:45). As I had opportunity, I feasted on this tale - aroused and horny! I just returned a package and am sitting in the parking lot ...closing my eyes, caressing my nipples and fondling and stroking my cock! It is cloudy, chilly and damp here in central TX. This makes me horny, multiplied by 100% by your story. My profile tells more about me ...and I answer emails. Like you, I love the feel of feminine lingerie, especially silky, satiny panties, thigh highs, negligees, slips, camisoles/tap pants. And I love a man dressed in lingerie! I also love sharing with other men, especially mature, bi-men (40+). So much more I could share. Drop a line if you want to share fantasies, encounters... BTW, I lived in MI, OH, WI and Chicago. Perhaps we have another common natural thread.

Share this Story

Similar Stories

Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
A Halloween Treat A Halloween Party with tricks and treats.in Transgender & Crossdressers
Ladies Night A group of friends try to get free drinks by posing as girls.in Transgender & Crossdressers
But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
More Stories