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Win or Lose?
My fiance, Steph and I have always been competitive with each other, but it is the punishments that make our bets or challenges the most fun. I don't even remember what the challenge was, but I lost it, and Steph was quick to rub my face in it. She informed me that Friday night she was collecting on my loss. I would get instructions on what I had to do for her later on in the week.
The closer it came to Friday, the more I looked forward, with anxiety of course, to paying for my defeat. Thursday night rolled around and I tried unsuccessfully to get some kind of clue as what I would need to do. She did not give up anything….instead saying, 'you will find out tomorrow after work."
Friday afternoon came around and I received a text, "you are to prepare dinner and serve it tonight." I thought, well that's not too bad, kind of mild for us in fact.
Just before I was ready to go home, I received another text with a grocery list and a recipe. "Go to the store and pick up all ingredients, then go home and start preparing." Dinner will need to be prepared by 7pm and your outfit is on the bed. You must wear only the outfit provided and serve dinner precisely at 7."
I thought okay, this seems more on the lines of our punishments now. But still, not horrible, so I have to cook and serve dinner. Come on, give me a challenge. I left the store after getting all of the necessary ingredients and I picked up a cheesecake for dessert. Steph loves cheesecake, so I wanted to surprise her.
I drove home and went to the kitchen to unload the groceries, I have some time before I need to serve dinner, so I took my time preparing our meal. I was mostly done with the preparation when I looked at the clock, 6:35pm. I need to do the final touches and prepare the table. I setup a place setting for her and one for me, lit the candles and went to retrieve my outfit for the evening.
I walked in and notice a small bag on the bed, with a note, "only the items in this bag are you allowed to wear." When I opened the bag, it was nothing but a pair of underwear. Silky, tight, and wait a minute, there were elephant ears and my tool would fill out the elephant's trunk. Inside the bag, there was also a bow tie with elephants on it. At the bottom of the bag there was another note. "Only the items in this bag!"
I hesitated but I knew that if I didn't complete my punishment it would be even worse the next time, so I slid the skimpy, ridiculous outfit on and went to finish the rest of dinner. Everything was prepared at 6:58pm and I waited another minute before I made my way, carrying our plates to the table.
I walked into the dinning room and there was Steph sitting there, in a beautiful black dress, and right across from her was Jen, her best friend, who was also dressed up in a pink dress that hugged her body perfectly.
They looked at the elephant and chuckled to each other. Steph asked me to get them some wine, which of course I did and poured each of them a glass. When I went over to Jen, Steph told her to check out how soft the elephant was.
When I started to walk away, Steph spoke up…"no sir, remember, you lost!"
I had to stand there as Jen touched me, "nice," she said, "really soft, but that's not always a good thing." They both laughed for a moment.
Steph looked at me and gave me more instructions, "okay, here are the rules, you cannot touch either of us, and you cannot get hard, if you do, the punishment will get a lot worse, do you understand?' I shook my head yes and went to grab another plate to eat with them. "Nope, you are to serve us only."
Steph reached into a small bag next to her chair and retrieved a small dinner bell, "when you hear this, you may enter the room and do whatever we ask of you."
I nodded my compliance and went back into the kitchen. I nibbled on the left overs in the pan for a few seconds then the bell went off, so I went back into the dinning room. "Yes, what can I get for you?" Steph smiled at me, "seems that Jen has dropped her fork, be a sweetie and retrieve it for her."
I bent down and went to pick up the fork when I saw Jen's legs open to allow me a view of the fact that she was not wearing any panties. She was fully shaved and her lips glistened as if she was already wet with excitement. I felt her hand rest on the back of my neck as she spread her legs farther, you know, to allow me to get her fork off the floor.
I picked up the fork and before I was allowed to come out from underneath the table, Jen guided my head to look across the table, that's when I noticed Steph's hand was between her legs, stroking her opening. She also was not wearing any panties.
Steph said, "get Jen a new fork please!"
I slid out from under the table and went to the kitchen to get a new fork. I brought it out to her, and went back to the kitchen.
I nibbled some more until I heard that bell again.
When I went to the dining room this time, Jen was now sitting right next to Steph, "can you bring my place setting over here? I want to eat closer to my friend."
I moved her plate and her wine glass, and her utensils and when I placed them in front of her, she grabbed my wrist and pulled my hand to her chest. She leaned her head back and allowed me to feel her, then she guided my hand inside of her top and onto her bare skin. I gently pinched her nipple before I removed my hand from inside her dress.
I went back into the kitchen again and was there for like 10 minutes before the sound of the bell brought me back to the table.
When I went out this time, the two women were standing up facing me. Steph was standing behind her friend, her hands roaming over her body, her lips were gently kissing Jen's neck. You could tell Jen was enjoying her treatment, and I, too, was enjoying the show.
Oh no, I said to myself, I need to calm myself before I get into trouble. The scene in front of me is already having an effect on certain parts of my body. Let's just say that the elephant's trunk is about to stand up and shout.
I tried to think of anything other than the scene unfolding in front of me, but I'm pretty sure the trunk will soon be completely outstretched.
I couldn't focus on anything else, I watched as Steph slipped the straps of Jen's pink dress off of her shoulders, her bare breasts staring me in the face. Oh, those look so good, perfectly round and capped off with pert nubs that are perfect for lips to suck on.
Steph's hands explored her friends breasts, lifting each breast, pinching each nipple, I watched as Jen loved this attention. Her neck bent the other way so that Steph could have full access to every inch of her neck. Steph could not get enough of her, she slobbered all over her neck and made sure I saw as her tongue slid all the way up from the collarbone to the jawline.
Steph knows me too well, she knows I have a thing about necks and her collarbone. She looked at me and I could tell the passion and lust was rising in her. She caught a glimpse of the trunk and asked, "is he rising?" I tried to hide the evidence but I think that only made me look more guilty.
Jen looked down and smiled at me, "I do think the monster is rising!"
Steph glanced at me and I knew I was in trouble, but what punishment was I going to get? Steph looked to Jen and nodded as if they expected this. Jen went over to her purse and retrieved a pair of hand cuffs. She came bouncing over to me and grabbed my right wrist. She dragged me over to the dining room table and locked my hands behind my back and around the leg of the table. Steph told me to behave and sit. Jen helped me by guiding my hips over the chair and making sure I was seated safely.
I did as I was told, as Jen went back to my girlfriend, as she walked across the floor, she moved her dress over her hips and down her legs. She was now completely naked in front of me and my fiance.
They met for a kiss as Jen helped Steph out of her dress. Both of them stood completely naked in front of me. There was no way that the elephant was going to relax. Jen grabbed my fiance by the hair and pulled her in for a very passionate kiss, I could see their tongues moving around each other's mouths. Their hands explored each other as well as I noticed Jen's hand was running between Steph's legs and sliding up and down her hairless seam. I could see Steph was enjoying the touch of another woman as Jen bent over to kiss her neck. The delight on Steph's face was very evident as her eyes were closed tightly and she moaned as fingers started to slide inside.
If I only had a hand free, I would be stroking myself, but I was bound to the table. Our dining room table is very solid heavy woodbwith a marble top, there was absolutely no way that I was going to go very far.
I caught a glimpse of Steph's face again, this time, she opened her eyes and caught my glance. She looked down and saw my trunk saluting her.
"More Punishment?' she asked, as Jen turned around and looked at me, they both seemed disappointed in me, but really what guy could be this close to two gorgeous women enjoying each other's naked bodies and stay soft. This time Steph walked over to the bag that was next to her chair and pulled a blindfold out.
She walked over to me and smiled a mischievous grin, "no peeking now, got to get you to calm down mister." She placed the blindfold and made sure I could not see, then kissed me softly, tapping on my erection as she walked away.
I heard them started kissing again, I could tell the passion between them was intensifying by the loudness of their moans. That was just as intense as watching them, the trunk was not going down as now I heard them going at it.
Moans got louder and I could hear the wet sounds of someone's honey pot. A few seconds of nothing and then a loud moan rang out loudly throughout the house.
I was pretty sure it was Jen as I have heard Steph moan many times in my ear, and it did not sound like her.
My imagination was painting a pretty vivid image in my head of what was going on, and it was just as exciting. I listened as the moans got more frequent and I was pretty sure that someone was going to be coming very soon.
I couldn't see, I couldn't move, and my erection was not going away, if anything the tightness of the ridiculous trunk was getting worse.
"Oh, fuck yesssssss!!!" Jen said as she went over the edge and came from whatever my fiance was doing to her. My erection struggled in it's prison to escape, but no, he was confined.
Suddenly I felt someone coming toward me, a sweet smell filled my nostrils as someone kissed me, I could distinctly taste someone's juices from a recent orgasm, I assume it was Steph, and that she just brought Jen over with her mouth and tongue. That was even more exciting than if I watched it. The smell, the taste and the thought of where her mouth was just, made my erection jump. I felt a hand on the fabric and suddenly she was pulling the trunk off of me and I moved so she could slid the thing down my legs.
Now I sat there bound and blind and completely naked. I felt hands on my naked body, my chest, my nipples, and yes, my erection was in someone's grip.
Lips left mine and then a new pair replaced them. My mind was spinning as someone took my entire erection deep into their mouth.
Her tongue sliding around my length as she went up and down with her expert lips. The feeling was incredible.and I knew with all of the excitement leading up to this that I would not last long. I felt delicate fingers caress my testicles as I was about to explode.
"Oh Fuck yes!!!!" I exploded deep into her waiting mouth. Her lips surrounded me tightly as her cheeks sucked in, making sure she got every drop of what I had to offer.
When my softening erection emerged from her lips, I heard them kiss, they moaned as they shared my taste between them. The sound of these two naked women had me starting to stiffen again in moments.
"So soon?" Steph asked, "my, you must be enjoying this."
Before I knew it, I was being forced fed a nipple. I sucked and swirled my tongue around as her hands held my head tight to her breast. I felt my hands free for only a moment and I was helped up from my sitting position. I could still feel the cold steel around my wrist as a hand grabbed my stiffening rod and pulled me around the room. Once we stopped moving, I was helped down to lay on the floor, I felt hands grab my wrist and put it above my head, soon the other hand was right next to it and the sound of the cuffs tightening around my other wrist echoed through the room. I was locked around something again, my arms could not move.
Still bound and blind I heard them kissing again, I imagined their hands sliding over each other's bodies, touching each other, caressing and fondling, my erection was definitely standing straight up again.
Once again, the sounds of them kissing slowly turned into moans. I could tell they were heating up again and I was eager to be more than a hearing spectator.
It wasn't long before someone was using my stomach as a pillow and her hair tickled me as I felt her grip tightly around my tool. She moaned as she worked my pole, sliding her hands up and down the full length. I am pretty sure that is Steph.
Unable to move really, I was the sensations coming from down below as she started to moan. Her head pressed into my stomach as she became louder and louder above me. He hand started stroking me faster and faster as I assume she is getting closer to her own release.
Her head moved back and forth over my stomach as she rapidly drew near to her own orgasm. I felt her lips wrap around my tool as her moans sent shivers down my spine. She filled her mouth with my erection, and stroked me with her hand until I was almost ready to explode again. She tightened her grip at the base of my tool and held tightly as she slowly climbed the point of no return.
One final moan as she crashed over she released her right grip and I flooded her mouth with my own explosion. She held my tool in her lips as I shot wave after wave deep inside of her mouth.
A few moments later, I had someone kiss me on my lips, softly at first, but then with more passion. I could taste the juices of excitement from her lips and tongue.
My tool finally resting as her lips let me slide out and onto my belly. The two of them started kissing again, and I could hear the moans. Then I heard a whisper and together, they said, "you taste so good."
I said smartly, "so do both of you!'
Whispers again, just quiet enough to not make out what was said. It didn't take me long to figure out what was said, when someone straddled my head and planted their womanhood right on my lips. I stuck my tongue out as far as I could, as it slipped inside of her. I moved my tongue in and out, slowly sliding it up and down to cover all of her opening in my saliva. She tasted incredible and when she grabbed ahold of my head and ground her lips into my face, I knew that she was in control. I stuck my tongue out as her hips moved back and forth quickly, until I reached her clit, then she sat down and my tongue circled around it.
I could taste her excitement building as I felt my tool slowly build back as a mouth surrounded me and slid down my soft member. I knew it wouldn't be soft for long as she sucked on me and caressed my testicles.
I worked on her little bud until she was starting to build. Just when I thought she was reaching that magical point, she lifted herself off of me. My hardness was released from it's warm, moist enclosure as well and then I felt it slide inside of someone as their pelvis met mine. She supported herself on my chest and slid up and down my pole. Her hips ground against mine as my hardness slid deeper and deeper inside of her.
Up and down, back and forth, I was standing strong and bringing her closer. Her fingers pinched my nipples as she moved, impaling herself on my hardness. I felt someone's hands between my legs, forcing them apart. Then I felt nipples on my chest, the girl who was riding me bent over and was now sticking her tongue down my throat. My legs were open and I felt hands sliding up the inside of my thighs, oh man, I'm not going to last much longer.
I was thinking of anything I could do I didn't fire away yet, I wanted to make sure that she finished again before I was done. As soon as I felt a tongue sliding up and down my shaft and hands start to gently rub at my balls, I was just about there.
I was staying strong fighting the urge to explode inside of her just yet. The woman on top of me came closer, as if that was possible, and I heard a whisper in my ear, "go ahead, release, fill me up with every last drop."
I could no longer resist as I felt her drop down on my erection as I grunted and did as she requested. I squirted inside of her as the walls of her opening squeezed me until she was moaning in my ear, "oh baby, that's right, come with me!"
I was still spasming when I felt my tool slide out of her. Her lips were quickly replaced by someone's mouth and I continued squirting. The lips sucked on me as I felt hands squeeze every last drop from my core.
When everything was said and done, i came three times in rapid succession. I don't know who received it and when, but I was soon released from my hand cuffs and left laying there, completely spent wearing nothing but a blindfold, which I quickly removed. Both of the women were completely dressed and sitting at the table conversation and drinking wine.
My mind was foggy and I was still reeling from my last orgasm, suddenly the bell rang.
"Honey, we need more wine," Steph said sternly.
"I also have dessert," I said, "would you like some?"
They looked at each other and giggled, "sure we can always have another dessert," Jen said with a smile.
As I went to the kitchen and got the bottle of wine and two slices of cheesecake and headed back to the dining room. I filled their glasses and Steph said, 'thank you for dinner and desserts, you can now go relax, we will ring if we need anything else."
I walked naked down the hallway and collapsed, completely drained, onto the bed.

© All rights reserved. Matt O'Bryan, author