Jennifer and Patrice Pt. 05

Patty and I were enjoying our breakfast. It was Saturday, we didn't have any engagements planned, just an easy day for us.

Patty asked "Jen, we've been trying all kinds of new things. And that exploring has been exciting for both of us. I have been wondering if your love for me has been holding you back from another experience."

I was kind of confused, and not sure what she was talking about. I asked "What would my loving you be holding me back from trying?"

Patty got a serious look on her face, and looked directly in my eyes and said "Jenny, I'm talking about you experiencing a man. A real man, not a silicone replica."

I was slow to pick up what she meant, because I had sucked a few guys off, that were close friends. Always when I was restrained, so what was she... then it occurred to me what she meant. She was talking about getting a guy to take me, and deflower me properly.

I responded with a long drawn out, "oh" and was quiet a moment to think through what she had suggested. Patty just waited patiently and watched me.

I continued, "well, I haven't given that any thought really. But it has crossed my mind before, when you have had me locked on our bondage table, blindfolded and gagged, that you could have a man come in and take me and I wouldn't be able to do anything about it."

Patty said "yes, and I had thought that before as well. But you know I would never do that without you having first agreeing and desiring it. Would you like that?"

I replied "you know I am a hopeless romantic. I want you, and only you. So, getting a guy to do this, I don't know... it's emotionally very weird for me. Would you feel like I was cheating on you? I don't really know how I feel about it."

Patty said "baby, you are overthinking this way too much! I'm not asking you about having a relationship with anyone, and you wouldn't even need to know who it is. We have plenty of friends who would love to do you, and are safe and healthy. And it wouldn't be cheating on me, I'd set it all up for you! It would just be a chance for you to just have a new experience, and it would be safe."

I was silent, my mind was whirling with thoughts and emotions and she said "Jen, there is no pressure. I'm not asking you to do it. It isn't for me. If you do want to do this, I am here for you and will set it all up. If not, that's fine too."

And with that, we moved on to other subjects and talked about our day. We didn't actually even discuss it for over a week when I brought it up one night after dinner.

"Patty, you asked me about having a guy take me, and it does sound really sexy and hot to me. Are you sure we can do that safely? And who would you get?" I asked.

Patty replied "Jen, if you want to do this. I will set it up. I think because of you being such a lovey-bug, and this will be just a one-night stand, it would be better if you don't know who it will be. And if you want to do it, there are a few rules I will want that you will need to agree to before I even start finding a dick for you."

I laughed at the thought, she was just going to find some dick somewhere for me. Not exactly what I was thinking, but essentially that was accurate. There wouldn't be any relationship, just one night of sex, I guessed.

I asked "what are your rules?"

Patty started in "One, you will buy a new outfit for this. Everything new, hose, shoes, corset if you want, teddy, body shaper, whatever you wear, it will be new. And it will need to look sexy enough to make a man want you really bad. Two, you will come home early on that day, get yourself ready on your own. I won't even be here. You will lock your cuffs on yourself, and you will use real locks to lock yourself onto the bench. You will gag and blindfold yourself as well. By doing this yourself, you will be showing that this is your choice completely. Three, you will be wearing your flesh-colored gaff and your false breasts will be glued on as usual. You will do everything possible to look completely like a CIS woman, or at least, as much as possible. Four, you will be giving permission to use your mouth and ass as I see fit, and as he sees fit. I will be there; you will never be alone with the men, and I won't let them do something I know you wouldn't want. Five, we need to get a noisy gadget to put in your hand to be your safe word. I'm sure we can find something for that but I want to make absolutely sure you have a way to call stop."

I was taken aback; she had really thought this out! Just listening to the rules made me horny to do this, so of course I accepted her terms. Patty pointed out that I will want to check over the bench beforehand, to make sure I can lock myself on without her help. She also teased me that she hoped I bought some really high heels to look super sexy, since I wouldn't need to walk in them much anyway.

Over the next few days, I found what I wanted to wear with a few trips to the mall and a trip to our favorite leather shop. I also went to our local sex shop and bought several penis shaped butt plugs with increasing size.

I didn't show Patty anything, including the plugs I bought because I wanted her to be as surprised as my suitor would be.

I had ordered new leather locking cuffs for my wrists and ankles in red to match my new outfit. After they were made and I picked them up, I checked over the bondage bench. I did need to put in a couple new eye bolts that were better positioned for ankles with the new shoes and ankle cuffs I bought.

It was Monday night, after dinner that I let Patty know that I was ready. She played around with her phone, messaging someone for a little while, then announced that it was confirmed for the following Friday night, just four nights away. I realized I didn't have much time, so I jumped up and went into the bedroom.

I pulled out the new large bottle of water-based lube I had bought, and the smallest butt plug. I lubed it liberally, and inserted it inside me, then pulled my panties up and went back into the living room. Patty was giving me a weird look, trying to figure out what I was doing.

Later, as we were watching the movie, I was squirming around a little in my seat, and she figured it out.

"You're wearing a butt plug, aren't you" she asked.

I smiled back "yep! I want to make sure I'm ready for this assault you have planned for me."

Patty replied "that's a really good idea. Are you going to wear it every night then?"

I answered "I am going to wear one every night while we watch our nightly movie, but I have different sized ones to progressively get bigger."

Patty squealed with delight. "Oh! I love that! That's brilliant, Jenny!" And she reached over, and squeezed a finger down behind my panties, and played with the end of the plug a little, to make it move inside me. I let out a little moan and gyrated my hips a little when she did it.

This went on every night that week. I'd put in a plug for the movie, and during the movie, she would snake her hand down so she could play with the end of it, and she thrilled me each time.

On Friday, I had gotten off a little early so I walked in the door right at five o'clock. I first moved the coffee table out of the living room, and moved the bondage bench in. I positioned it so as people walked into the room, they would see me from the side, and easily be able to tell my helpless situation.

I ran a quick cleaning towel over the bench so it was sparkling clean and there wasn't any dust on it anywhere.

Next, I went in the bedroom and stripped, took my shower, shaved everything super close with a new razer, and quickly dried myself off.

I first glued my false breasts on, holding them carefully in place until the glue dried. Then I put on my flesh-colored gaff. Due to my hormone therapy and exercising, I had an acceptable female shape. Standing in front the mirror, I looked like a naked woman with wet hair and no makeup. I quickly opened the new package, and pulled out my red thigh high stockings with the line up the back. I carefully put each on, making sure the line was perfect.

I had also bought a red satin strapless bustier. It improved my female shape even more, and looked really sexy.

Then I sat down at our vanity and did my hair and makeup. I was particularly proud of my red lipstick which matched my outfit, even though with a gag on, you wouldn't see it.

My next thing was to put on some new red, elbow length opera gloves I had bought. Then lock on my new red leather cuffs on my wrists and ankles. I knew that I was kind of going overboard with the red, but I also felt it would be sexy and worth it. At least to me, anyway.

All I had left was my shoes. And I wasn't going to the shoes on until I was ready to lock myself on the bench because with 5-inch heels, I doubted I could walk in them anyway.

I checked the clock and saw I had less than a half hour to go. I grabbed my gag, blindfold and shoes and headed for the living room.

I did a quick scan of the room, making sure everything was in place. I ran back into the bedroom and grabbed the bottle of lube. I placed it on the floor right by where my feet will be. I wanted to make sure it was easily visible.

I checked to make sure the keys to the locks were all hanging on a hook on the bench, out of reach of me, but easy to get to for Patty.

My pulse rate was racing as I sat on the couch and put my gag on. This was also new, made with red leather, and had a fairly large dildo custom sized to my mouth attached. I slid it into my mouth, then locked the straps behind my head. I then slid the blindfold on my head, but not covering my eyes yet.

Then I put my shoes on. They were strappy sandals, and although some women think it's tacky to wear hose with sandals, I loved the look that day. You could easily see my bright red toenails through the red sheer hose I was wearing.

I carefully walked over to the bench. I spread my legs wide, and carefully bent down and clipped the locks I had already hanging on the eye hooks onto the D rings on my ankle cuffs. I carefully used the bench to steady myself as I stood up.

I carefully laid down across the bench, making sure my body was as comfortable as possible since I would be there a while. I put my arms down in place, next to the lock hanging on one of the bench legs. Using my dominant hand, I clicked the lock shut.

I was now mostly helpless. I just had one wrist to go, so I pulled my blindfold down, getting it perfectly in place. Then reached down to the other bench leg, I felt for the lock and managed to get it positioned right and then clicked it shut.

I was now alone with my thoughts. I pulled at my wrists, and they couldn't move much at all. Maybe an inch at most. My high heels were standing on the floor, but not completely supporting my weight because of laying on the bench. I tried to move them, but could not. I tried shifting my body around on the bench, but could hardly move. I began thinking about the dong in my mouth. It almost completely filled me up. I could not run my tongue along it, because my jaw would hurt from opening that far.

My chin was resting on the bench, allowing me to look forward, at least it would if I had not blindfolded myself. I started to wonder, should I have put a butt plug in place? Would this guy be huge? Patty wouldn't get someone who would hurt me, but how would she know? Then I realized the obvious, she knows exactly how big I have taken with our strap-on. If she used that for a guide, then she would know if he would be too big. Wait, how would she know how big he is? Would she get him hard and measure him?? Was she sucking the guy off to get him hard?

My stupid thoughts were thankfully interrupted by hearing the door open. I heard the sounds of high heels on the tile floors, but also other footsteps as well. It sounded like more than two people. Who all did she bring home??

I heard Patty's voice "Oh Jennifer! You look lovely!!! I would love to take you myself! But you know we have guests for that purpose tonight."

I could hear male voices laughing but suddenly felt headphones being slid on my head. I heard Patty's muffled voice "baby, I see you forgot to put your safety device in your hand! Luckily, I thought you might get distracted so here it is."

I felt her slide an elastic band around my fingers and down to my palm. The elastic was holding the plastic remote against my palm and as I closed my fingers, I could feel a button in the middle.

I heard Patty's voice again, "yes, that's right baby. You just push that button and it will make a racket to get our attention. And now, since I don't want you to know who is here, I am going to play the sound of ocean waves to keep you company. If you are okay with this, and you want me to continue, nod your head." Which, I happily did.

Moments later, all I could hear was the sound of ocean waves crashing against the surf.

I felt hands, touching me all over my body. They were caressing my bound body. Someone was caressing my head, another was caressing my back, more on my ass, even hands on my bound legs. I moaned in my gag, it felt so gentle, so kind and loving to me.

Then whoever was petting my head, removed my gag. I was moving my jaw around a little, because it had been stuck in one position for a while, and someone inserted their dick in my mouth. I focused on pleasing him. Licking him along his shaft, then wrapping my lips around him. In spite of my efforts, I really didn't have any control because of the way I was bound. He had control, and slid in and out of my mouth as he liked. I could only wrap my lips tightly around him as he slid out, and try to accept him as well as I could when he slid back in.

I don't know how to do the throat thing, I'm not that experienced. But I did my best to not gag if he went in too deep. It wasn't long before I felt him grabbing my head with both hands, and quickening his pace. Then I felt him tense up, and prepared to swallow what I could, but he pulled out.

And immediately, I felt lubrication being applied to my ass. Some fingers going inside, making sure I was well prepared. Then I felt the familiar feel of Patty's strap-on dildo pushing against me. I loudly gasped as it slipped inside, and someone else took advantage of my open mouth, and stuck the biggest dick I have ever experienced into my mouth. I didn't know there really was anyone that large! My jaw was opened as wide as I could, just to get the tip in. He was kind and didn't try to shove it all the way in, I couldn't have dealt with that at all. I sucked on him, and licked the tip as best I could while someone was banging away in my ass. I was moaning and gasping at all these sensations going on.

Whoever this guy was, he just held the tip in my mouth and let me lick and suck on it. I was hoping they weren't planning on trying to stick that in me, that would hurt... probably pretty bad.

After just a few minutes, I felt the dildo slide out of my ass and quickly it was replaced with a real dick. This was all new territory for me. I could feel the heat of his body as he teased me by pressing against me, but not going in. I felt his hands on my hips, gripping my bound body tightly.

I was getting a little confused, having this monster in my mouth and another at my ass, waiting to come in. Thankfully, the monster in my mouth pulled away, and I felt a ball gag being slid into my mouth and buckled behind my head.

I was thankful, because it allowed me to just experience the man who was now sliding slowly inside me. It felt like he was similar in size to the dildo Patty usually uses on me, so I wasn't getting too stretched out. Instead, it was just the wonderful sensation of this hot piece of meat inside me. I laid there, unable to move much, feeling this unknown man hammering away in my ass. I could feel his body pressing against the flesh of my ass with every deep stroke. It wasn't long until I felt it getting bigger inside me, and his body was tensing up, then he came inside me. I was expecting to feel liquid flowing, but there wasn't any so I realized he was wearing a condom. I was glad, I don't want to take any risks with my health, but also a little disappointed because I wanted to feel that too.

After he pulled out, I felt hands caressing my back again. My ball gag was removed, and I felt a straw at my lips. They were giving me a little break and a drink. I didn't try to talk. I was overwhelmed with emotion. I was also so excited, I would normally have already had my own orgasm, but with my thing tightly tucked away in my gaff, that wasn't going to happen in the conventional way.

After a few minutes, my straw was taken away again, and replaced with another dick. This one was relatively small, and was so enjoyable to me to suck on! I could lick him on the bottom, and when he pulled back a little, I could lick the tip, then suck it back deep into my mouth. It continued to get harder inside my mouth with my ministrations. I then felt the now familiar feel of them grabbing my head and sliding all the way into my mouth. It just reached the back of my mouth when I felt his body pressed against my face. I could feel the smooth hairless skin as he pressed his body against my face.

I don't care for pubic hair, so the fact this guy was clean shaven made me hungrier to please him. The fact he fit so well in my mouth was equally exciting to me. I made more efforts to suck and please him then realized, I know this penis! I've sucked it before. This is my sissy friend Betty! Somehow, that made it a little more special to me and I was inspired to try to please her even more. I say "her" now, because that is still how I see Betty.

My attention from Betty wasn't exclusive, I felt someone lubing my ass up again. Then someone was pressing their dick against my ass and slid it in. I gasped around Betty's member, this new guy was bigger than the last guy, in both girth and depth. He went in deeper than I had experienced before. I'm sure it would have hurt if I hadn't already been so excited and used.

I felt him pull almost all the way out, then grab my ass and play with it. Then he gripped my hips hard and slammed back inside me. I was whimpering as Betty started taking control and taking my mouth with abandon. Whoever was in my ass, started doing the same thing. It felt like they were trying to coordinate both going deep at the same time. I was absolutely squealing away as their pace continued to grow. My mouth was being used and abused, and my ass was too. My own sexual energies felt like they were at an all new high. My own orgasm was growing inside me, building and building. My lover in my ass tensed up and came inside me. This time however, I felt it flowing inside my body. That sensation pushed me over the edge and I came too. My body spasming and convulsing out of control. Betty must have enjoyed the sight, because almost immediately, she came in my mouth too. Thankfully, she pulled out though so I didn't have to try to swallow all of it. Instead, I was able to just lay their enjoying my body coming down from my orgasm, and feeling my lover in my ass get soft inside me, then pulling out.

After a few minutes, and I had calmed down, I was offered straw again so I could get a drink of Pepsi. Then, after another few minutes, my penis gag was replaced in my mouth. I thought it was odd that she switched between the ball gag and the penis gag, but Patty is a creative creature so no telling what she had in mind.

I felt my wrists being unlocked, then my ankles being unlocked. There were several sets of hands on each side of me, helping me to stand up. Two people were holding each of my hands, pulling them out from my sides as someone else wiped down my sweaty body and cleaned me up.

They pulled my hands behind my back, and I felt chains being locked to my wrist cuffs, and then my wrists were raised up and locked close to my collar. Someone stood on each side of me, and they walked me presumably into our bedroom. They both needed to steady me, because I was still wearing the impossibly high heels.