“I’m so glad you made it!” Jessica said as she opened the door. I walked in and received a big hug from her.
“Yeah this is gonna be a fun weekend!” I replied. Jessica grabbed my hand and pulled me through the house.
“I’ll introduce you to the other guests.” She told me. On the back porch overlooking the beach I saw two large black men sitting and drinking beer.
“Luke this is John,” pointing two the slightly smaller man, “and this is James.” The men stood up and we shook hands and introduced ourselves.
I had always kind of had a thing for Jessica. She worked just down the hall and seeing her made my day. But standing next to these two big muscular men, I felt so un masculine. How could I kid myself into thinking Jessica would want me when there are these strong sexy men all around her.
We continued on with the evening, going out to dinner at a nice beachfront restaurant. I couldn’t help but notice Jessica and John flirting more and more as the night progressed. I really had no chance with her.
“John and I are gonna go grab something from the car we’re gonna be right back.” Jessica said with a giggle. John took her by the hand and the two walked away.
Now I was alone with James so I decided to make some conversation. He told me he worked for the park service, which I thought was really cool. After a while of getting to know each other I had decided James was a pretty cool guy.
Finally, Jessica and John returned, now with their arms around each other. Even though I was sad, the two did look really good together. After they sat down, James looked at Jessica and then back at me.
“So Jessica tells me you are bicurious and possibly looking to experiment with guys.” James said. I looked over at Jessica in shock, speechless, I felt betrayed.
“Oh don’t worry sweetie they don’t judge. In fact James is bi himself.” She said confidently. I felt a bit better but was still uneasy. I hadn’t shared my sexuality with many people and was still slightly uncomfortable thinking about it.
“I mean I don’t know much about it but I think I feel some attraction towards guys as well.” I responded shakily.
“No pressure to put labels on it. Everyone is a unique person. I just try to enjoy myself.” James said. The conversation slowly shifted away but I was still thinking about it. I’d always been curious about possibly sucking another guys dick, but had always been scared to do anything about it.
James and John paid for the meal and we headed back to the beach house. Once we got there Jessica hopped out of the car but James and John stayed in.
“We were about to head to the gym for our night lift. Do you want to come Luke?” James asked. Now I’m not the skinniest person but am 5’7” on a good day and about 130 lbs. I knew if I went with them all I’d be doing was embarrassing myself. Luckily, Jessica stepped in and saved me.
“No Luke don’t go with them because then I’d be all alone here,” she said, “Stay and hang out with me.” I gladly obliged and James and John headed off. Finally alone with Jessica, I was excited.
I grabbed two drinks and headed out to the back porch. After the two of us talked for a while and finished our drinks, Jessica interrupted the conversation.
“Hey I know this is kinda silly but would you be interested in helping me dress up?” She asked.
“Sure sounds like fun.” I replied casually. Really I was ecstatic that was spending any time with her.
“Perfect!” She squealed and pulled me up thee stairs to her room. Opening her dresser, I saw loads of sexy panties, bras, booty shorts, skirts dresses, crop tops and more. It blew my mind. All of a sudden, Jessica pulled her skinny jeans off, revealing a pink lace Victoria Secret thong.
“I think my ass looks great in these.” She said as she posed in the mirror. I froze, afraid that if I spoke the words would come out of my mouth all out of order. Jessica looked to me, waiting for a response.
“I think that thong could make even me look great!” I replied awkwardly.
“Yeah! So do I.” She said happily, “Let’s get them on you.” It took me a few seconds to realize that she was serious. When I finally knew she actually wanted me to wear her panties I was shocked.
“What? I’m a guy.” I replied, trying to wrap my head around it.
“Pretty please? It’d make my day.” Jessica asked, making her best puppy eyes, “And you’re about my size too.” I didn’t really want to put on the thong but I also wanted to make Jessica happy.
“Fine. But you owe me one” I said grumpily.
“Yay!” She yelled ecstatically. After an awkward silence, she started slowly peeling the soft pink fabric off her smooth butt. As she turned to face me, her beautiful pink pussy became visible.
“Your turn!” Jessica said with a smile. I stood there for a second, taking a few deep breaths. I fumbled pulling down my khaki shorts. She giggled and walked over getting on her knees. My semi hard cock was visible under my boxer briefs. Jessica wasted no time in yanking them down. My small 3” dick flopped out.
“Aww it’s so cute!” She said sweetly, “I’m glad you have a small penis it’ll look better with panties.” I had always been slightly ashamed of my quite under average dick, but Jessica made me feel better about it. She laid the thong at my feet and guided my feet through it, slowly puling it up my long toned legs. The lace felt so good wrapping around my hips. My small cock fit perfectly in the skimpy fabric.
“OMG it does look great on you!” Jessica said ecstatically. I turned around to look in the mirror and she was right, my ass looked great. Spinning around a few times I admired my slim body and noticed that it did look rather feminine. My frame was slender and my butt was pretty juicy. I wasn’t really that muscular and didn’t had quite narrow shoulders.
“Here put this on too.” Jessica ordered, as she handed me a matching bralette. I obediently slid it on. My body felt so sexy wearing Jessica’s lingerie, I’d never experienced this kind of feeling before.
“This is kind of embarrassing but I actually feel really good in these.” I told her. There was just something about wearing slutty panties that was amazing.
“I’m so happy to hear that!” Jessica said gleefully. Just then we heard the door open.
“Hello. We’re back!” John shouted. Jessica wrapped a towel around herself and ran out to meet them.
“Get your bathing suits on we’re going to the beach!” She yelled from upstairs, “We’ll be ready in 5 minutes.” I remembered that my clothes were still in the car, but didnt want to go out dressed like this. Jessica walked back into the room and grabbed a pink bikini from the drawer.
“This one is for you.” She told me. I was ok with wearing the panties in private but I wasn’t sure about with John and James. I mean I had only just met them.
“Come on! Let’s see if they think you look as good as I think.” Jessica commanded. Reluctantly I took off the panties and bralette and stepped into the bikini bottoms. I raised my arms and she put the top on.
Next Jessica pulled out a matching bikini in red. After stepping into it, she lifted her arms up. I carefully slid the smooth fabric over her arms and positioned them over her firm breasts. I couldn’t hide my raging boner, even with my small size.
“Come on let’s go!” Jessica said. The two of us ran down to the beach where John and James were already waiting. As we approached the men smiled when my outfit became visible.
“I like the look!” James said with a smile.
“Thanks. Me too!” I replied.
“Last one in the water is a rotten egg!” Jessica shouted. The four of us sprinted down into the waves. We splashed around and enjoyed the warm salt water, bobbing up and down as we floated on our backs. After a while, James spoke up.
“Who’s up for a chicken fight?” He asked. All of us shouted in agreement.
“Me and John vs Luke and James!” Jessica declared. She hopped up onto Johns shoulders and splashed me. James picked me up with his muscular arms and placed me on top of his broad shoulders.
“Ready. Set. Go!” Shouted Jessica. James and John ran towards each other. I grabbed onto Jessica’s leg and yanked on it. But her other leg kicked me right off James into the water.
“I demand a rematch!” James yelled. We continued to go at it until it was too dark to see. I hadn’t had that much fun in a long time.
We grabbed our towels and headed up to the house. There were two outdoor showers, John and Jessica got in one, while James got in the other.
“You can shower with me, I don’t mind.” He said. I thought about it for a second before stepping inside. I began to rinse off but the space was so small we were being squished together.
“Is it ok if I take off my swimsuit?” James asked. I was slightly shocked but intrigued. I’d never seen another guys cock in person before, but I wanted to.
“Uh. Sure go ahead.” I responded shakily. James slowly pulled down the swimsuit. The base of a thick black cock became visible. As he continued puling it down, more and more of his huge dick became visible. It was amazingly long. Once he had completely removed them, the entirety of his 9 inch manhood hung down. James smiled as my jaw dropped.
“I can see that you like my BBC.” He said while chuckling and pointing at my crotch. I looked down to see my thin baby dick rock hard. Embarrassed, I blushed from cheek to cheek.
“It’s nothing to be ashamed of.” James told me, “You can get a closer look if you like.” I immediately went down to my knees. The sight of this beautiful black dick inches from my face was driving me crazy. Gingerly, I stuck my tongue out to taste the tip. It was too much to handle.
I took the head of James’s thick cock into my mouth.
“Mmm you like Daddy’s dick?” James’s said. I responded by pushing my lips down his thick shaft. In response, he gently placed his hand on the back of my head, beginning to guide his cock in and out of my mouth. At this point he was rock hard and leaking precum. The taste of the salty liquid made me work harder to pleasure him.
The hand on my head grabbed ahold of my soft blonde hair and pushed the cock to the start of my throat. With steady pressure I was able to take daddy’s cock in my throat. Once it was in, he kept pushing until his fat black dick was balls deep.
“I guess you were a sissy slut all along.” He said. Slowly, he began throat fucking me. I gagged every time it entered my throat but it didn’t matter. The smooth black skin sliding in and out of my mouth, stretching my lips all the way. As I became accustomed to the presence, the speed of the thrusts sped up. Daddy’s big dark balls slapping against my chin.
I worked my best to please him, swirling my tongue around his member as it slid in and out. Sucking as hard as I could. Daddy pulled his cock out and rested it on my face, letting his balls hang into my mouth. He stroked the thick monster while I licked his balls.
After a minute or two, he shoved his BBC right back into my mouth. Face fucking me as hard as he could. I was enjoying every second of being used by this strong black man. I was his cute white sissy fucktoy.
Eventually, I heard a moan escape Daddy’s lips and felt him sliding his monster dick out of my throat. My mouth was filled with his thick creamy load. The taste his cum was amazing. Daddy pulled his black cock out and it continued to shoot out his hot sticky semen, covering my face. I obediently swallowed his warm seed like a good slut.
Daddy wiped the remaining cum on my outstretched tongue and smiled as it spurted out the last bit of cum.
I could tell this weekend was going to be a lot of fun.
Source: reddit.com/r/Erotica/comments/c5ukxg/a_sissys_first_cock_mm_oral