Weekend Fun Pt. 02

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The drought is over and the weekend fun continues.
2.9k words
4.69
9.5k
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Part 2 of the 5 part series

Updated 06/10/2023
Created 12/31/2020
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Jfdf
Jfdf
64 Followers

After leaving Evan's place, I stopped by the liquor store and then drove straight to the party. I felt good while I drove...I had taken care of Evan, or more accurately been used by Evan for his pleasure. I didn't get off; but his cock felt good, I got to swallow his hot cum and the weekend had just started. I got to the party and joined those that were already there in the spacious backyard.

I recognized about half the people there as co-workers and chatted with a few of them. As the night went on, I relaxed and had a good time, meeting some of the attendees that didn't work at my office, including one particularly interesting couple. After getting to know them a bit, I gave them my number and eventually moved on to spending time with a woman that I was friends with and hadn't seen in awhile.

Her name was Olivia, she was petite and a year or two younger than I was. She had blonde hair down to the middle of her back and perky boobs that I guessed were about a B-cup. I had gotten to know her a little and knew that she had something of what I would describe at the time as a kinky streak, but didn't know anything more specific.

Olivia was having a good time, but she decided that she was ready to head home early. She had gotten a ride there and was pretty buzzed, so I offered to give her a ride home. We both said our goodbyes to everyone that was still there and hit the road. It was only about a 20 minute drive to Olivia's house and the ride was uneventful, mostly just small talk and laughing.

When we got to Olivia's house, she invited me in for a drink. I gladly accepted, mostly because I wasn't ready for my night to be over so early. I had no idea what kind of fun that drink would lead to. We walked inside and she poured us both a drink. We continued the small talk and laughed while we drank and it didn't take long for me to be feeling a god buzz. The conversation gradually turned sexual and Olivia, who was among the few that knew I was bisexual, suddenly asked me a very direct question.

"Have you ever been pegged?"

I was caught off guard by the question, but answered her after a moment, "I have not." I was keenly aware of the plug still in my ass at that point and breifly recalled the fucking that I had already received from Evan before the party. Olivia had a big smile on her face and said she would be right back before disappearing from the living room we were sitting in.

When she returned, she was carrying a bag and sat down next to me on the couch. She removed a box from the bag and showed it to me. The box appeared to have never been opened, but it was clearly an 8 inch strap-on. Olivia still had that smile on her face as she showed it to me.

"I have always wanted to peg a guy and I bought this when I thought my last boyfriend would be into it." she said

"What happened?"

"We broke up before I ever got up the nerve to discuss it with him. It was for the better anyway, turned out he was an asshole."

I killed the rest of my drink and teased her. "So, do you want to discuss pegging then?"

She hit my arm playfully and said bluntly, "No, I don't want to discuss pegging. I want to peg YOU tonight!" she said. That was the last time she was playful that night. I was incredibly horny at that point and was more than willing. Since I admitted that I was bisexual, I had wanted to be pegged by a beautiful woman and here was a golden opportunity.

"Well, if that's what you want, then let's do this." I said.

Her demeanor changed and she took on an authoritative tone to her voice that reminded me of Evan earlier that night. She stood up and told me to follow her. She led me back to her bedroom as I admired her ass. I had never really noticed it before at work, but she had a nice firm ass that I reached out and grabbed as she walked.

As soon as we were in her bedroom, she ordered me to strip. I pulled my clothes off quickly and watched as she did the same. I admired her toned and fit body as we both removed our clothes. She removed her bra and I saw her perky tits, her nipples hard and begging to be licked. She removed her thong panties last revealing a tight, pink pussy that looked absolutely delicious. My own rock hard dick was in full view and pointing at the ceiling.

"Fuck, you are beautiful." I said.

"I know, now get over there and lay down." she ordered, pointing at the bed.

I moved to the bed and laid flat on my back. As I climbed on the bed, she saw the plug that was in my ass. "You have a buttplug in!" she laughed.

Olivia climbed on the bed next to me and swung her leg over me, straddling my chest. "As long as you remember that I'm in control her, that I'm fucking you tonight, we'll both have a real good time." she stated as she looked down at me.

"Yes Ma'am." I answered enthusiastically. The dominance that she was suddenly showing turned me on even more and I wondered what all she had planned. I didn't have to wait long. She shifted herself further up the bed until her pussy was hovering over my face.

"If you want me to peg you, you have to earn it." she said as she sat her pussy onto my mouth. I started to lick her pussy like my life depended on it, tasty her pussy juice. It was as delicious as it looked and I couldn't get enough of it. She grinded herself onto my face and I alternated between fucking her sweet pussy with my tongue, darting it in and out, and licking and sucking her clit. Her moans got louder and more frequent, telling me that she was enjoying herself.

After a few minutes of savoring her pussy with my mouth, she lifted herself off my face. She turned around and sat back on my face, lowering her puckered rosebud onto my mouth. I started to rim her ass with the same eagerness that I did her pussy and her moans resumed, just as loud. I reached around underneath her and felt her pussy. I found her clit and started to rub it as I rimmed her ass.

I licked her ass and rubbed her clit for what seemed like forever and her moans kept getting louder. Without warning, she pushed her ass into my face and clamped her legs on me. I felt her body tense and she practically screamed as her first orgasm of the night hit her. When her body finally stopped shaking, she got up and climbed off the bed.

"That felt great, but I want to fuck you and I would say that you've earned it." she said as she got the strap-on out of it's box. I watched as she stepped into the harness and tightened the straps around her. Olivia's new 8 inch cock looked good on her and she got used to having it on for a moment, swinging it back and forth.

"You like this, do you?", she asked. Without waiting for an answer, she continued, "I like it and since I already know you like to suck cock occasionally, get over here and show me how you suck a cock."

I moved off the bed, got on my knees and slowly took the lifelike dildo into my mouth until I eventually had it all in my mouth. It was a little bigger than Evan's was earlier, but I was able to suck the whole cock into my mouth. I started to bob my head on her cock and looked up at Olivia.

"So this is what it's like to get a blowjob?", she mused as she looked back down at me. She put her head on the back of my head and pushed my head onto her cock and held it there. She let go after a few seconds, but not completely and kept my mouth on the head. She started to fuck my mouth with her cock, easily at first and increasingly faster. She was clearly enjoying the exchange of power as she fucked my face, listening to the sounds of the sloppy blowjob that I was giving to her "cock".

Olivia kept this up for a couple of minutes and by the time she stopped face fucking me, I had salivia hanging off my chin. "Take that plug out of your ass and get on the bed, doggy style!" she abruptly ordered. My mouth was sore from the fucking she gave my face and I replied "Yes Ma'am." I took the plug out of my ass for the second time since leaving my place earlier that evening and set it aside before climbing on the bed.

Olivia climbed up behind me and I felt the cold lube that she squeezed onto my ass.

"Since you decided to have a plug in tonight, I guess you don't need any warming up." Olivia said sternly. A few more moments went by as she rubbed lube all over her cock. I felt the head of her cock at my hole and felt as she started to push into me. She slid in inch by inch slowly until her big cock was buried inside me. I heard a small moan escape her lips as the inside of the harness pushed against and rubbed her clit.

She didn't wait before pulling her cock out of me until just the head was left inside. She held it there for a moment before she pushed it back into my ass and staretd fucking me. Olivia fucked me slowly at first, but quickly picked up the pace. I was moaning as I was being fucked for the second time tonight, only this time it was by a beautiful woman.

I could hear her moans as the strap-on harness rubbed against her clit each time she fucked her cock into me and they matched my own moans. I could feel the pressure against my prostate as she fucked me, alternating between fast and slow. After a few minutes, she really started to pound her cock into me as hard as she could, pushing my face into the bed with each thrust.

When she suddenly pulled her cock out of me, I felt empty and wanted to be filled up again. "Get on your back!" she ordered as she sat on the bed behind me. I rolled over, expecting her to push her cock back into me. Instead, she had loosened the straps and she climbed onto my cock, impaling her pussy onto my hard dick. Her pussy was dripping wet, soaking my balls as she rode my dick hard, with her "cock" bouncing in front of her and slapping my stomach.

I was building to an orgasm when she tensed up and slammed her pussy down, burying my dick inside her. I could feel her tight pussy spasm on my dick and she screamed as she had her second orgasm of the night. When she was done convulsing, she didn't waste any time. She climbed off my dick, stopping my own buildup to orgasm, and tightened the harness straps again.

"That was amazing, but I'm enjoying this too much to be done with you!" she stated with a domineering tone that I had never heard from her before. She lifted my legs onto her shoulders and lined her cock up, shoving it back into me hard and fast. She started fucking me again without waiting and started rough, pounding into me hard and fast.

I moaned loud as she fucked me and could really feel the pressure on my P-spot. She had a large smile on her face as she fucked herself into me and reached down and smacked my ass several times. My own dick was harder than ever before and leaking a steady stream of pre-cum. She saw this and rubbed her fingers in it as she kept fucking me. She never missed a thrust or slowed down as she reached her fingers up and stuck them in my mouth. I sucked her fingers and tasted a delicious mix of her pussy and my pre-cum.

"You like my cock? You like how I fuck your tight ass with this big cock?"

"Yes Ma'am." was all I could answer between moans.

That seemed to excite her as she started to piston into me even harder. It seemed like she was already building to another orgasm as she grabbed my dick and started to stroke it. I knew I wasn't going to last long after the intense fucking she was giving me.

"When you cum, you're going to clean it up."

When I didn't answer her immediately, she let go of my dick and smacked my ass hard.

"Did you hear me?" she asked almost angrily.

Once again, my only response was "Yes, Ma'am" as she continued pounding her cock into me roughly.

She started to jerk my dick as she fucked me and I felt my orgasm building again. After only a minute of being fucked and jerked off at the same time, I passed the stopping point. Olivia sensed the same and slammed her cock into me as hard as she could and held it there as the first jet of cum erupted from my dick.

She held my dick straight up and leaned forward, causing the first jet to hit her tits. She then pushed my cock down as jet after jet of cum pulsed out of my dick and I could feel my ass clenching around her big cock, buried inside me. When my dick was finally done pulsing, I was covered in my cum all over my chest and stomach. It was by far the strongest and best orgasm I ever had.

Olivia kept her cock buried in my ass as she scooped as much of my cum off my chest and stomach. She rubbed some more on her tits and then reached around and rubbed the rest on her ass. She slowly slid her cock out of my ass and the empty feeling was there again.

"What are you waiting for?" she said sternly. "Clean up your mess!" she demanded. Without saying a word, I sat up and started to lick my cum off her tits. I licked all over both of them, sucking her nipples and making sure my cum was completely off her. She started rubbing her clit while I cleaned and sucked her tits.

"Don't forget the rest of your mess, get it all!" she demanded.

I wanted to suck her tits more, but I obediently moved to lick the rest up. She got on her hands and knees on the bed and I moved behind her. I licked her ass cheeks first, licking my cum off of them before I moved to her asshole. She was still rubbing her clit as her cock hung down and I dove into her ass. I licked up everything she had rubbed all over her asshole and then kept eating her ass. I darted my tongue into her puckered hole repeatedly as she rubbed her clit.

I kept up eating her ass for a few minutes, her moans getting louder. "DON'T STOP! LICK MY ASS! OH YEEEEAAAHHHHH!" she practically screamed. Her ass suddenly clenched on my tongue as I ate her ass and she screamed again as she reached her final orgasm of the night. When she was done, we both collapsed on the bed and caught our breath.

We talked some and she admitted that "exchange of power" was a major turn-on and she said she hadn't orgasmed that hard in a long time. After we rested for awhile, we got cleaned up and dressed. My ass was sore from the two rough fucking I had gotten that night and I didn't put my plug back in my ass. We walked to Olivia's front door and before I left, she kissed me. She thanked me for a good time, I thanked her for the same and I left.

I got into my truck and checked my phone. It was 1 AM and I had a message from a friend of mine, another woman that I had originally met through work, but didn't work with, who had been at the party too. I had not gotten the opportunity to spend any time catching up with her before I left though.

"You left the party early and I didn't get a chance to talk to you. You up for a good time?"

The message was sent about 15 minutes earlier. I read it several times, decided that maybe I wasn't ready for the night to be over after all.

"Yes, yes I am. What did you have in mind?" I responded as I wondered what else could be in store for me this night...and this weekend.

Jfdf
Jfdf
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2 Comments
AnonymousAnonymousalmost 3 years ago

Every submissive guy needs to feel vulnerable and feminine, ordered to serve a dominant and be spanked, treated rough, given a chance to be a bottom. It doesn’t matter if it’s by a male or female.

Just admit it and enjoy the feelings.

AnonymousAnonymousabout 3 years ago
Dreams Of Getting Pegged by a LadyBoy

Ah, this story was so fucking HOT !! My long time fantasy of mine being that I too am a Bi-Sexual Male , is to be pegged or Fucked in My Ass Pussy by a Pretty Ladyboy with an 8 or 9 inch Hard Cock or a pretty petite lady peg me with a Strap-On Dildo Cock and Fuck Me ! I have Two Strap On Black Leather Harnesses and a small collection of various sizes of realistic Dildo Cocks to choose from ! I LOVE Asian Ladyboys the most !

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