Valentine’s Date
By kas456.
I had been with Brandi for a few years; she had me in the palm of her hand and knew it. At the beginning, our sex life was amazing, then things got sort of stagnant for a while. We had begun to explore some things in the bedroom, and things had been getting better both there and out. We would share our thoughts and ideas and explore them together. She was very submissive at the beginning of our relationship until one day:
“We can try anal on one condition,” Brandi said after a couple of conversations about it.
“Ok, what is that?” I asked.
“So if you can fuck my ass, I get to fuck yours! Fair is fair!”
“What do you mean?”
“Pegging! I know you know. Strapon will be here this weekend, so you’ll get your wish!”
I nervously replied, “Are you sure you want to do this?”
“Yes, we are doing this; you’ve begged for this for a while now. I was talking to Caroline the other day, and she suggested it.”
“Babe, I’m not comfortable with you talking to your friends about things like this.”
“Sorry, I didn’t know what to do, it’s going to happen, sweetie, we can both get something we want, I’m in a hurry, I’ve got to get to work!”
My mind raced for the next few days. I had no idea what to expect or how my weekend would go when I clocked out on Friday. When I got home, I was met with a surprise. She met me at the door wearing some of my favorite lingerie, a bustier, a garter belt, and stockings, but as she came out of the shadow, I could tell she was wearing a strapon as the head of her lady cock bobbed around.
“I couldn’t wait! I had to put it on! Isn’t it awesome!”
“Well, it’s…”
She stopped me as she put her finger over my lips. “Trust me, it’s going to be fun! Go get undressed and meet me in the bedroom!”
I was getting turned on by this point. It was great to see her so excited and happy again; it was a bit like things used to be. Her confidence was so sexy. I walked into the bedroom with a smile on my face. She was looking at herself in the mirror; she had on her plastic cock.
“The kit came with a few, but the other was way too small. I want this to be fair,” as she looked at my swollen member. “Looks like this one is a bit bigger than you!”
My face turned red, and I was ashamed.
“It’s ok, baby, you take really good care of me, and you always finish me somehow, but I do feel like the one with the bigger dick gets to do the fucking first!”
I was at a loss for words at this point as she led me to the bed, “Just get on your hands and knees, like you always tell me!”
I did as she requested, and before I was fully situated, I felt cool lube in my ass crack.
“I’m not sure I’m ready, babe.” I stammered.
“Relax, I got the best lube for this,” as I felt the head of her dildo slide up and down my crack, I could feel tension building deep in me. Suddenly, she pushed in, and with a deep breath, the head popped in.
“Good boy,” she whispered. I felt so vulnerable, yet so turned on. She began to thrust into me slowly. In my mind, I didn’t want to like this, but it began to feel so good. I let out a few moans and whimpers, but I was still having a hard time taking it.
“Does it hurt? Do I need to use more lube?”
“Yes, sweetie, maybe we can try some other time.”
“The time is now!” She exclaimed.
She didn’t have quite the mercy this time. I felt her head at my hole, and before I knew it, I could feel her hips on my ass.
“I knew it would fit!”
She slowly began to thrust again. Then began to speed up.
“Oh fuck!” I moaned.
“Oh, you like it! I thought I was hurting you!”
She began to thrust harder into me and faster.
“Take my lady cock!”
A heavy spank landed on my ass, then she grasped my hips harder and fucked my ass as hard as she could. I was at a loss at this point. She ran her nails down my back and would continue to lay a hard spank once in a while. I could feel an orgasm brewing as she rammed into my prostate. My body began to convulse she slowed down. I’d blown my load all over the bed and had gone limp.
“Looks like someone likes this a little too much.”
“It feels so good, babe!”
“Don’t babe me! Call me Goddess!”
Something was unlocked in her that day, and our relationship would never be the same. I still haven’t gotten to fuck her ass. Every time she locks me up, my mind goes back to that day.
It was Valentine’s Day, and amongst all of the things we had explored between now and then, we both had brought up bringing someone else into our sex life. I could get another female if she could get with a different guy. We talked it over briefly, and she found a guy she was going to meet.
“This might be awkward, the two of us meeting a guy, what if I can’t get it up?”
“Oh, sweetie, you won’t need to worry about that!” she said.
We pulled into a strip mall, and she parked in front of a place that does waxing.
“I’ll just wait here.”
“No, I made an appointment for you, too! You’re getting waxed too, we gotta take your cage off here, thought,” she said as she pulled out her necklace that had my key on it. “You need to be cleaned up, too. You’ll be meeting up with Caroline later!”
“What!? I didn’t even know!”
“I feel bad about not letting you get your piece of ass after our last deal, so I am making sure it happens this time. I know you have the hots for her, and she already knows everything about our sex life anyway, so why not?”
I started to get erect as she removed my cage, “Don’t get too excited too fast,” Brandi said.
We went in, and I was already humiliated. We both survived our waxings and went down the strip mall to a lingerie store.
“How does it feel? smooth?” Brandi asked.
“It’s definitely interesting!” I said
She grabbed a few things and began walking to the fitting rooms, motioning for them to follow.
“I’ve got to get you locked back up before you get too excited. We wouldn’t want that. Would we?
“Yes, Goddess,” I replied.
“Good boy, I hope you do a good job pleasuring my bestie tonight, because I’m going to do the same for you.”
“Dave?”
“Yes, Dave, you guys are good friends like Caroline and me, I just thought it would be easier.”
“Well, I I…..”
“At this point, you don’t have a choice!”
I left the changing room while she tried on a few things. It seemed like she had bought a lot of stuff when we went to check out, but she was definitely spoiling herself today.
“I rented rooms and made reservations for us. You will meet up with Caroline at 5 for dinner; the rest is up to you. I am going to go over to her house to get ready!”
“What about my cage?”
“Patience, it will be taken care of, just don’t be late! I will see you tomorrow morning!”
We embraced in the strongest hug we had in ages, with the most passionate kiss.
“I want to fuck right now, but I don’t want to screw up our day, I’m so fuckin wet!”
“Love you!” we both said as she walked out the door.
I got ready and arrived at the restaurant about 10 minutes early. I guess at least I wasn’t meeting a stranger; we had spent some time together in the past.
“Good evening!” I hear.
I turn to see Caroline in a black dress that ends just above the knee. Her stockings were so sexy, I looked up to her beautiful face, noticing my key around her neck. My cock strained in its cage.
We went in, got our food, and the evening was going very natural. Everything was going great; we even joked about what Brandi and Dave were doing.
She bumped her fork, and it fell to the floor.
“Mind getting that for me?” Caroline winked.
I began to bend under the table, and she had her legs spread wide. In the shadows, I could see her slit barely glistening. I knew she was wet.
“Ready to get out of here?” she said.
“Yes!” I said.
We began to scurry off to the hotel room. As we went inside, she began to pull her dress off, revealing a sexy black longline bra, a garter belt, and stockings.
“No panties to save a step,” as she walked to me and we began to make out.
I was still dressed at this point, and we ended up passionately making out on the bed.
“Well, first thing is first, I need to see if that mouth is as amazing as Brandi says!”
I began to set up, and Caroline pushed me back down and waved a finger. She straddles my face as she lowers her pussy down into my face as I begin to get to work. Still not sure if this is a dream until I feel my cock once again straining. Suddenly, Caroline begins to undo my belt and slide my jeans down, revealing my locked cock.
“Oh, so it is real? I thought she was just playing mind games with me!”
I try to tell her yes, but muffled sounds are all I can make as she grinds her pussy even harder down on my face.
“No worries, Adam, Mommy will take good care of you!”
My caged cock twitched, “Oh, I’m glad you like that, because I sure do!” She continued to ride my face for a while before pulling herself off.
“Get naked! now!” Caroline said, so I began to strip.
I held my hand out for my key.
“No, no! This is mine! We will see if you earn it! shaved even! trying to make him look bigger?”
“No waxed.”
“She really does have you, huh?”
“Yes, mommy,” I said as she smirked.
She spotted a bag and walked to it, “Your girlfriend left us a bag of goodies I might need.”
She dug around a bit and found a blindfold, putting it on me as I sat at the end of the bed.
“Well, I’m so horny I’m going to let you fuck me first before we have any other fun.”
I hear her rustling around in the bag.
“Let me get this on you, though!”
I could feel her putting something on me. straps something, she asked me to stand up, and I could feel her tighten a few straps around my waist.
“Can you please unlock me?”
SMACK, across my face, “Don’t question me.”
“Yes, Mommy,” I said.
“Lie on your back!”
So I did, I could feel her straddle my legs and began to move up.
“Don’t want you missing the good part!” Caroline said as she pulled the blindfold off. She was begging to insert a head of a dildo in her. I then noticed she put a strapon on me.
“I said you were going to fuck me, never said with your own dick!”
She began to ride me, then got up into reverse cowgirl so I could watch her perfect ass bounce.
“Yeah, I’m sure you wish your cock were in me, but this was how we knew you could stay pussy free today! I’m getting kind of worn out. I need you to do the work!”
She got into doggy style as I began to take her from behind with the strapon. She began to scream as she squirted everywhere.
“Fuck, that felt good. Please clean me up a bit,” she motioned my head to her pussy, I lapped up her amazing-tasting juices.
“Wait here,” she said as she went to the restroom. “Go ahead and take the strapon off.”
I did, and she came over to the bed and grabbed a larger dildo from the bag, attaching it to the harness before sliding it up her waist and tightening it down.
“Now my fun starts, I’ve never pegged a guy before, but I know Brandi has taken you, that was my idea!”
I look at her nervously.
“What are you waiting on? Get in position!”
I did, and no sooner did she have her lady cock buried in my ass, thrusting deep. She began to flog my back as she railed me deep. Im moaning into the pillows at this point, cock ready to explode.
I hear the door open and tense up.
“Looks like you two are having fun,” I hear Brandi say, “Dave let me down, fucking 5 pump chump. I hadn’t even gotten into it yet before he blew his load.”
Caroline continued to fuck my ass as Brandi positioned herself in front of me, pulling her skirt up, revealing her pussy with cum dripping out.
“Clean me up and get me off!” Brandi demanded.
My mind went wild as I ate my friend’s cum from my girlfriend’s pussy while her best friend fucks my ass. I had no idea how long this night would last, but I knew it would be long.
The End.
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