Penny - Friend Asked to Watch Ch. 01

Please note, this is a true story. However, I've changed the names, ages, places and occupations to protect the other person's privacy. I have no shame so enjoy, LOL. The series follows the events after Penny - The Bridal Suite and The Bridal Limo.

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Friend Asked to Watch Ch. 01

They said they'd never do anal; guess they were wrong.

Do girlfriends tell each other everything, well it depends. Penny was more reserved and never used to talk about her sex life with her friends. That was until she met me and the events that happened at her friend Ashley 's wedding day. She's become more confident and more comfortable talking about sex. My "naughty" influence so far has made some positive impacts.

They had known each other since college and were good friends. Madison or Maddy as she goes by stands 5'5 with a 32DD chest but not much of an ass either. She was more sexual experienced and had more boyfriends then Penny did. Maddy had just gotten out of a 4-year relationship pre-Ashley & Martin's wedding. She was supposed to hook up with a groomsman but he got too drunk to do anything. And she became more sexually frustrated as she spent the night next to a passed-out man instead of being fucked by said man.

The next day at work, it was early evening and they were working late. Both of them worked together doing admin for a fortune 500 company. After the rest of her co-workers left, Penny told Maddy about what happened on that wedding day. As she started going into more of the kinky details, Maddy fell out of her chair. Obviously, Maddy was shocked. She knew Penny was not the type to engage is such sinful behaviors. Penny did keep out the part about Charles (Martin's dad). That would've really blown Maddy's mind.

Later that night, Penny called to tell me she let Maddy in on most of the details of our kinky fun. Penny had described our sex life as if it was the kind of sex you'd see in porn with how hot it's been. Maddy's curiosity got the best of her and at the end of their conversation she asked Penny if she could watch us fuck. We would be performing a live action porn for her. I could tell the way Penny brought this up she was "strongly" considering it.

I said, "I've got a really busy week and I'd think about this idea." Yes, I was going to make her wait and stew on what I may be thinking. Even though I knew it would be a yes. I know it was so wrong by making her wait. However, it put her on pins and needles waiting to hear from me about this all week. And that is how I wanted her.

From my experience, I knew not only would Maddy watch but it would turn into a full scale 3 way. But, I would have to direct the action so to speak. Before what happened in the limo Penny never engaged into a 3 way before. Sometimes it takes certain person to bring out aside of you that you didn't know you had. As for Maddy, I didn't want to ask Penny too many questions about her. I did not make her feel uneasy.

For me group activities was something I indulged in a "few" times. I was not looking for this to become a typical FMF 3 way. I wanted to amp this up to a next and memorable level. I had remembered a conversation the ladies had during the wedding festivities about how none of them would ever do anal. During the week I went to an adult shop to buy some items to "help" the 3 way to the next level.

Meanwhile, the next 3 days at work for Penny and Maddy were a bit antsy. Maddy was surprised that after all the kinky stuff I'd done, I would have to think on it. This point really confused them just as I had wanted. Later on Thursday evening, I called Penny and told her I'd be out of town for work the next few weeks. Although, this weekend I had an assignment that was only an hour south and I invited them down for dinner on Friday night. I purposely reserved a large suite overlooking the water.

"If you ladies wanted to stay, they could take the bedroom." I said.

Penny asked, "Can I...could I stay the whole weekend."

I replied, "Sure if Maddy drives you down here I can drive you back before I fly out. And as a thank you for driving I'd make sure she'll be rewarded with a tasty dinner and maybe even catch a show."

"Oh that sounds like fun, let's do it. Would you like me to wear something sexy?" she asked.

"Who says you'll be wearing anything this weekend." I playful replied.

She got off the phone and called Maddy right away. She figured Maddy could drive her down. Then we'd hang out and Maddy would be "entertained". Afterwards she'd drive home later that night so we could be alone. Maddy agreed and didn't pack a bag. They had no idea what they were in for.

Friday after work, they leave work together and jump on the freeway heading for my hotel. Penny packed a small bag with some "clothes" she snuck out at lunch to buy. In the car they tried to talk about some ground rules if a show was put on. Penny who had told me she loved me in the limo and didn't mention it again since then was planning to have a special weekend with me where she'd hope I say the same back. She wanted Maddy to leave quietly after she got to watch some of the "show". They had worked out a signal, which in hindsight did not go as they planned.

As they were driving down, I was preparing the suite for quite the "festivities". I had the hotel bring up an extra robe and pre ordered room service. As a non-drinker I had some nice regular and non-alcoholic champagne. The "stuff" I got from the adult shop was strategically placed around the room. I had candles and a waterproof audio device set up in the bathroom. Everything was timed to a T. As soon as they get close, I'd start the motions. If only I'd thought of bringing a camera or did I.....

Penny called and said they were 5 minutes away, just as I had asked. Adding in elevator and parking time I had realistically about 10 minutes. It was 635pm. It takes me about 90 seconds to light the candles. I scheduled room service for a 7pm deliver time. I had her call again when they parked so I could give them the room number and start the candles. Wait a second, why candles in the bathroom and room service. Were we eating in there?

As the call came in, I went to the bathroom and lit the candles. I kicked up of my feet on the couch and waited for them. A few minutes later there was a knock at the door. I walked over to open the door and was greet by a big hug from Penny. Then I looked over and gave Maddy a welcome to my suite hug. I put Penny's bag down and offered them a shower. I said, "I know y'all been working all day and the long drive. I set up the bathroom for you ladies to shower and freshen up. We still had a little time before dinner." Would they take the bait......

Penny said why not and asked Maddy to go first since she wanted some quick "alone time" with me. I interjected and said Penny should go first since I wanted to shower with her. Of course she was down for that. What I was really trying to do was get us both into a robe after the shower. It would be easier to get Maddy into one instead of getting back into her regular clothes if she saw us in them. And the robes were key to my plan.

As I opened the door and they both see the candles and relaxing music playing, they were pleasantly surprised. How thoughtful and sweet I was, were the comments I got. In the shower, Penny wanted to fool around. However, I needed to watch the clock and I wanted to give her a sensual teasing shower. I lathered her whole body up in a steamy erotic way. I paid extra attention to between her butt cheeks and the holes I was going to enter. The whole time she closed her eyes and just got lost in it.

Once we finished, I dried her and myself off. I pulled out the robes and wrapped both of us in one each. I kept the shower running so it would be hot and steamy in there for Maddy. I purposely guided her into the bathroom and showed her where her towels were and a really nice robe I put out for her. As I left I intentionally didn't lock the door. Not to be creepy but I would convince Penny to slip in and grab her clothes so she'd have to wear the robe.

While she was in the shower the food came so Penny and I wasn't able to really get frisky yet, just as planned. We spent the time putting all the food out as I ordered a sizable spread. I told her to sneak in and grab Maddy's clothes out and if she was going to watch us, I would only agree to it if she wore the robe. I instructed her to put on the 3-inch heels I had told her to bring. I needed them to be close to the same height for my plan. Penny was 3 inches shorter than Maddy.

Just about 15 after 7pm, Maddy started to come out of the shower wearing the robe. Looking relaxed she asked Penny if she had her clothes. I distracted her by pointing to the large spread of food. I knew Maddy would be hungry after work and the long drive she wouldn't be as focused or at least a little chill about her clothes. And I was right. Maddy saw the platter and didn't follow up about it.

I had re-positioned the hotel furniture in a way that would best suit what I needed done. Time was of essence in situations like this as when time stalls people lose interest. I moved the table and chairs by the window so we could see the view. I had moved a lounge chair close, very close to where I had wanted Maddy to sit. We spoke about some random topics with our drinks, appetizers, seafood entrees and an assortment of fruit.

When I noticed they were almost done eating I say to Maddy, "So I hear you had some major disappointment at the wedding."

She blurted out, "I have been so horny since it had been 3 months since I got laid last. The guys I've been out with since my break up have been lame."

For Maddy, the wedding was an excuse for fuck a random guy. One who would be flying away the next day so she didn't have to deal with slut shaming. She worried too much about one-night stands. She didn't want a bad rep and a have nice guy would pass on her for marriage. Slut shaming is a real fear many women have but I wish it didn't exist. Live and let live!

That was my queue. I grabbed Penny by the hand, lifted her up onto the lounge chair "conveniently" next to Maddy. I opened my robe to expose my cock and moved Penny's mouth onto my cock. Then I forcefully started to thrust my hips so I was avidly face fucking Penny. Maddy had a stunned look on her face. I pulled Penny off my cock and looked at her. My exact words were "Suck my cock like it's your last meal!" She began aggressively sucking my cock. I looked over at Maddy and her mouth was wide open.

Our eyes met. I was looking at Maddy when I said to Penny, "You love sucking my cock don't you?"

Penny responded, "Yes."

I asked her again more firmly, "I said you love sucking my cock don't you!"

While never taking my eyes off Maddy, Penny replied with a stronger "Yes!" Maddy leaned back in her chair. She slowly moved a hand up her thigh and into her groin area. She spread her legs and I noticed she had a nice, trimmed landing strip. Once I saw her rub her pussy, I knew I wanted her to rub it more violently.

I lifted Penny up, threw the lounge chair to the side and spun Penny around facing a few steps from the wall. Slightly away from the spot we were just in. I pushed her forward against it and in one motion slid my cock into her as she was bracing herself against the wall. I savagely penetrated her with powerful thrusts after powerful thrusts. I was still looking right at Maddy, the harder I penetrate Penny the faster and stronger Maddy was rubbing herself. Penny kept screaming, "Oh my god, Oh my god, Oh Taylor, fuck me, fuck me."

Then all of a sudden I pulled out and stopped. I walked over to Maddy, pulled her to me and then up against the wall next to Penny but with a little space between them. Penny had also turned around to see what was happening. My left hand was on Penny's left shoulder; my right hand was on Maddy's right shoulder. As I looked back and forth quickly from both of them getting their eye contact.

I moved my hands down their bodies quickly and slapped both their clits at the same time. A pleasurable and painful moan came from their lips. Then I slid a finger into both of them. I moved the first finger in and out of them with a few thrusts. Then a second with more thrusts. And not long after I found a perfect rhythm. As such I started to pump and vibrate both my hands and fingers.

There was a lot of "oh fuck, oh my god, oh Taylor's" being thrown around. In a perfect world I would make them both cum at the same time, but it worked out better I didn't. Penny came first and gushed everywhere. She collapsed down to her knees. With my left hand now free I pulled her face onto my cock. I looked deep into Maddy's eyes and said, "Are you ready!" She knew what I meant was ready to cum but didn't expect me to pull out my fingers and with a strong smack hitting her whole pussy. It caused her to shiver and release her fluids that went everywhere including onto Penny.

Maddy was barely able to stand, she leaned forward onto me. I raised my right hand up to her face. Our eyes meet, she looks at me with desire and I pull her in for a dynamic kiss. I wanted her to feel fireworks and I found out later she did. My goal wasn't to make her fall for me. It was making her lust for me, in and for this moment.

If you put a thermometer on us the results would have been smoking hot. The kiss was so powerful from both of us I barely even felt Penny sucking my cock. I was careful not to hold our lips together for too long. I didn't want love, I wanted lust. So I broke the lustful embrace then started it again, then again and again. Maddy's eyes looking at me after the last time I broke the kiss said it all. I swear they said, I have to have you!

I pulled Penny to her feet then spun Maddy around this time placing her hands against the wall. My wet hard cock started to penetrate then ravage her pussy. As I focused on fucking Maddy, I told Penny to pull her hair with one hand and smack her ass with the other. This was so fucking hot! However, I was going to spice it up more. I told Penny to talk dirty to her friend while also giving her something she wanted. "Ask Maddy if she likes your man fucking her pussy."

There I said it, I acknowledge to her and Maddy that I was Penny's man. I know that made her very happy. Penny completely in awe, smiled lovingly at me. Her voice changed into a new demeanor. The sweet, shy and quiet Penny used the tone a dominatrix mistress would use. "Do you like my man fucking your pussy" she said while pulling her hair and spanking her ass.

Maddy let out a scream "Yes, I love it, I need it, fuck me more."

Penny responded "You want more you little bitch."

"Yes, please I want more" Maddy replied.

I was moving my cock in and out of Maddy at a furious rate. I took her hair from Penny and told Penny to suck on one of her nipples. I kept up my pace while Penny was hungerly sucking on her nipples. As if she was trying to get milk from them. Maddy's moans and screams were music to my ears.

The sight of the 3 of us with Maddy's sounds was a marvelous scene. With her mouth still attached to Maddy's breast, I told Penny to reach down and pinch Maddy's clit just like I did to her on our first date. She shot me a look like oh yeah I remember that "pinch". As such she pinched and tugged her clit quickly and there it was. "OH FUCK, OH FUCK", Maddy screamed as she trembled in ecstasy. Her legs were unsteady and barely able to stand. As I carried her to the chaise lounge sofa, she weakly said "I can't feel my legs".

While Maddy laid down to regain her breath, I moved back over to Penny. Pulling her to my face and kissing her intimately. My hands held her face as I warmly kissed her. She was taken aback by my switch from lust to tender kissing. And just as she settled into this embrace, I just had to switch it up on her again. Of course I did, typical me. This poor lady is living this whirlwind of unpredictability and constant roller coaster of emotions. But she wasn't complaining and loving every moment of it.

I surprised her by picking her up in my arms and carrying her over to the chaise where Maddy was catching her breath. I set her down on her feet and grabbed Maddy's legs pulling her to the edge of the chaise. I moved Penny on top of her. Penny was in a position knees bent squatting above Maddy in a variation of the missionary position. Maddy's knees pushed back onto her sides, Penny's thighs basically sitting against Maddy's thighs. Penny's legs off to both her sides.

I grab a strategically placed double head dildo from under a clean towel hidden under the chaise. They were both pretty wet already so I didn't need any lube. I guided one end into Penny and the other into Maddy. Both women stunned and frozen in place. I smacked Penny on the rear. With that she jumps up a little and falls back down.

The dildo moves inside both of them causing both to let out moans. I lift Penny's hips and push her down. I start doing this motion repeatedly. Basically I was using gravity to fuck both women with this toy. After a few moments they seemed to start enjoying and getting into it.

Penny started bouncing herself up and down. Both these women were speechless so to speak with everything that's happening. They were just going with the flow. I loved women who could enjoy the moments in life and not always be in their head worried about others judgement. As the bouncing continued, I spread Penny's ass cheeks and started to tongue her hole. I paid extra attention to cleaning the area while we were in the shower.

I started licking delicately at first. Creating more of a sensual feeling. This was her first analingus! After initially being stunned she was certainly enjoying it. I grab 2 black disposable gloves and some lube again from under the chaise. I wet 3 fingers on each hand then put one at Penny's asshole and one at Maddy's asshole. Here we go!

I start to massage both rear openings on both women. They were not expecting any of this tonight let alone what was about to happen next. I slip 1 finger into each hole slowly. Both gasped and both stopped their movements. I told Penny to keep fucking Maddy. As she started bouncing again, I got my finger fully into each hole and left it there a moment for them to get used to. Then I pulled out and in with a slow pace to begin with. As they started to get used to the sensation a different moan escaped their lips. A moan I haven't heard from either. It was a mix of pain and pleasure.

Not long that sound came off as more pleasure. I slip a second finger in both of them. Going slow again for them to get used to. Some "oh my god and this is unbelievable" were coming from their mouths. As my second finger started going in easier, I started moving it faster in and out of both of them.

More moans and sounds of delights filled the air. It encouraged me to go further. Now a third finger begins entering them. I wasn't going to get my whole hand in there. However, I was planning to fill them with "something else".

I kept my hand in Penny but pulled it out of Maddy. I grabbed a condom from under the chaise and ripped it open with my teeth. My left hand slid the lubricated condom onto my hard cock and with Maddy's hole with some lube in it already, it was time. I place the tip of my cock at her anal entrance. Slowly the head pops in. An "oh fuck" escaped her lips. My right hand still pumping in Penny's asshole but now just 2 fingers as it was easier to do 2 fingers then 3 while I was trying to put my cock into Maddy's ass. This was not my first time doing this.

My hard cock slips past Maddy's external anal sphincter and deeper into her asshole. The shocking sensation was not lost on her. Oh my god he's really putting it in my ass, was what she told me she was thinking. As for now all that was coming from her mouth were sounds of pleasure. Once I finally got all in, I held it there for her to get used to.