Breaking the Bridesmaids Ch. 05

It was late Saturday afternoon, quickly becoming Saturday evening. As we sat in the hotel room, drying off and changing from our extra-curricular activities in the hotel pool, I reflect that the weekend was now more than halfway over.

The weekend was all about one thing, Anna, my wife Amanda's friend from high school and one of her bridesmaids, admitting that the fact that she had been wrong to pressure my wife into sex behind my back throughout our relationship, and especially at her bachelorette party.

So far, I had made limited progress towards that goal. I was holding the specter of revealing Anna's wild activities to her employer and coworkers over her head, which earned me a modicum of control, but overall, Anna was still not anywhere near admitting her fault.

I had to kick it up a notch. I told the girls to put the sundresses they had worn earlier that day back on.

I went into the bathroom to pee, and when I came back out, Anna was ready to go, wearing the green and white sundress I had lifted up to finger her to orgasm in a restaurant bathroom at lunch.

The dress was tight on the redhead's top, showing off her dancer's body and long legs. Her b-cups were hanging loosely, and I could tell she had nothing on under the dress.

My wife Amanda was ready as well, though she had to be reminded to remove her bikini bottoms from under her red sundress. I admired her long legs as she did, her long brown hair covering her embarrassed face as she removed the only clothing under her thigh-length dress. I stared at her chest, and convinced myself there was no bra on her A-cups.

As she shot them down her legs and off, my wife asked:

"Where are we going? It's way too early for dinner."

I nodded. "We have one more shopping stop to make."

Poor girls uncontrollably sighed at this. Anna's was defiant, but Amanda just looked tired.

I looked at my wife, having one of those 'conversations via look' that only couples can.

"Honey, I'm exhausted."

"Are you kidding?"

"Please?"

"Ughh, fine."

"Thanks babe."

With that, Amanda headed towards the bedroom. Anna, oblivious to the language we were speaking, watched her and looked back at me expectantly:

"We're not going?"

I considered my options for a minute.

"No, she is catching a nap so she is ready for tonight's activities. You are still coming with."

I walked into the bedroom to find my wife lying on the bed. She was just settling in. I leaned down and kissed her, whispering "Sweet dreams."

She barely whispered "Thanks" in response before she fell asleep.

I walked back out to find Anna with her arms cross, full 'bitch mode' in effect. What was it going to take to break this girl?

"Let's go." I growled.

This trip was too far to walk. We didn't talk on our way to the car. Anna was trying to silence to her advantage, but I refused to bite. Plus, I had an advantage.

"My car?" She blurted out when I pressed the unlock button and her BMW honked in response.

I nodded, and got in the driver's seat. I could hear the fiery redhead huffing as she got in the passenger's seat.

I pulled out of the hotel and immediately caught a red light.

Without looking, I reached over and began to idly stroke Anna's thigh. She didn't resist, but did nothing to assist.

"Where are we going?" She asked, sounding honestly inquisitive.

"One more stop" I said vaguely.

Being a touristy town, there was a red light at every corner on the main street we were on, and they were timed out of sequence to prevent cars from getting up to speed.

Combined with the Saturday shopping crowd, it meant we spent a lot more time going zero than above it.

I wasn't upset about it. The slow drive gave me plenty of time to tease Anna's nether regions, and by the time we got close to our destination I had the firebox on a nice low simmer, just how I liked.

When I pulled into the parking lot and parked, Anna saw where we were and huffed out a 'Ughh, yuck."

Before she could continue her response, I barked out "Stay here" and quickly jumped out.

Finding an adult store in the town wasn't easy. This one was off the main strip, but its web presence was significant enough I was able to find it.

I hadn't originally planned to have to make this trip, but since Anna had not been remorseful to my liking yet, I decided it was necessary.

Speaking to the proprietor, I was able to quickly procure what I needed. Returning to the car, I put the bag in the trunk and climbed back in.

"What did you get?" Anna asked, sounding sincere.

I looked over at her like she was an idiot.

"I think you will find out."

With that, we repeated the trip back to the hotel. This time Anna tried to situate herself out of range, but a quick nipple pinch correction solved that. By the time we reached the hotel Anna's legs were wide open to my touch, pussy exposed, along with her left breast which I had removed from the sundress.

She was lost in the clouds, not noticing we were parking until her brain realized that both my hands had left her body.

"Clean yourself up." I said as I got out and retrieved my package.

The walk back to the room was uneventful, unless you count my groping of Anna's bare ass in the elevator while an older couple stood in front of us.

By the time we got off, even I could smell Anna's pussy in the air.

Again, simmering. Just how I liked it.

When we got in the room, we still had over an hour, so I decided some cleanup was in order.

Amanda was still napping, so I sent Anna in to shower while I called to confirm our dinner reservation.

That only took a few minutes, so I took the opportunity to torture the redhead some more. Entering the bathroom, I sat and watched her in the shower.

Since she hadn't showered since arriving in town, my wife's friend found the shower extremely enjoyable. Her luscious red hair hung over her shoulders, its color darkened by the water, contrasting even more than usual with her pale skin.

Her back was arched, pushing out her pale, freckly breasts, slightly upturned, nipples at attention, water rushing over them. Even with her heels flat on the ground her ass was accentuated by her natural curves, topping her long, dancer's legs.

She was absolutely gorgeous, but she knew it, and I think that's why she was such a bitch. She knew guys would give her the benefit of the doubt.

Satisfied that Anna wasn't satisfying herself, I walked back out into the bedroom and awoke my sleeping wife with a kiss.

After our swim, I thought she might want a shower, but she declined. It wasn't until she felt my hand way up under her skirt that she woke up with a sultry "hmm".

I guess the nap had restarted her motor, because I put her on a simmer too, before Anna emerged from the bathroom.

She was wearing a towel around her head, and a second around her body.

I shook my head 'no' at her, and she scowled, but removed the lower towel, exposing her freshly washed body to my sullying eyes.

Anna went to her bag and pulled out some type of lotion, which she started applying to her legs. It wasn't meant to be a sexually arousing act, but considering how hot she was, almost anything she did naked would be.

"Anna, I am a little disappointed. I thought I had given you enough moisturizer already?"

That earned me another look from Anna, but a giggle from my wife.

Since they were both engaged, I decided to unveil their outfits for the evening. While the sundresses were 'decent' and hadn't received too much protest, I expected some resistance this time.

My wife I liked to dress in red, and tonight was no exception. The dress Amanda would be wearing was short and tight, barely covering her ass. The top was split in half, leaving her breastbone exposed to well below her breasts, and tying behind her head, hanging loosely over her chest. If not properly maintained, what time she didn't spend covering her ass would be spent covering her tits. The fabric was stretchy, so it would form-fit her gorgeous frame, and I knew it would be a hit with any guy we saw.

Anna's dress was gray. The color was perfectly neutral and contrasted nicely with both her hair and her skin.

The dress had to be pulled on, it was also stretchy, which meant it was tight in all the right places. The top half was basically a giant loop of material that started behind her neck and looped over her breasts.

The way the top was done meant her back was mostly exposed. The only thing holding the bottom half up was about 6" of fabric across her stomach that connected the loop to the skirt. The bottom half was stretched tight around her ass, but again, one tug. The skirt ran to mid-thigh.

I could see that neither girl was taken with her dress, but I knew every guy we saw would be.

I quickly pushed them to get dressed, and when they were, inspected them, tugging her and there.

They both looked gorgeous, albeit slutty.

While they did their hair and makeup I changed into a suit.

When they were finished, I told them both to pick out their shoes. I took the opportunity to unpack my bag from the adult store.

When the girls were properly heeled, I handed each a box. They each opened them and sighed, clearly not happy with what they were given.

"Well, you wanted to wear panties. So I got you panties".

Anna's were a sheer, black thong. I don't think her objection was to that. I think her objection was to fact that the panties contained a vibrator. A vibrator that I now demonstrated for her by pressing the remote in my pocket.

"If you are a good girl, I will give you the remote" I said, ignoring her response and turning to my wife.

Amanda's box contained a pair of panties as well. But her's was a 'strap-in'. They were red, matching her dress, and pretty small cut, but contained a snap on the inside of the crotch where a black dildo was mounted.

"Don't worry honey, I didn't buy the deluxe model with the butt plug. And if you are a good girl, maybe I will let you turn it inside out so you can fuck Anna with it."

I chuckled, seeing the girls' disgust. At this point; however, they knew better than to argue, and proceeded to don their assigned underwear.

Anna's thong showed no lines, but Amanda's dong required more support, and the panty lines across her ass were clearly visible.

It was even more obvious that something was up when my normally sure-footed wife nearly waddled down the hallway to the elevator.

Once there, I could see her fidgeting with the panties, trying to make the phallic invader as comfortable as possible.

In the elevator, I goosed the remote and was rewarded with Anna nearly jumping out of her shoes. I chuckled, but we decided to turn the dial down a little. After all, the goal was to stimulate her, but not so much it was obvious.

Amanda's gait did not improve in the lobby, and even though the restaurant was not far away, I decided it would be better to drive.

This time we took our car, since Anna's backseat was tighter than her ass. Well, probably it was. I planned to find out later in the night.

Getting in the car proved to be difficult for Amanda. She sat shotgun, and watching her shifting in her seat concerned me.

"Don't like that cock?" I asked playfully.

"No, its not that. The straps, they cut into me. But if we loosen them, the damn thing will rattle around inside me."

I could hear the pain in my wife's voice, and felt empathy. While she was being punished, I didn't want to cause her physical pain for no reason.

"Okay, take it off."

There was a heartbeat afterwards where both girls said nothing. I think they were both surprised I had shown pity like that. Once they recovered, both spoke at once:

Anna blurted out "Me too?" while Amanda said "I'm sorry, don't be mad."

Their reactions showed me which girl was properly penitent, and which one still needed some work.

Stopping hard at yet another red light, I reached over and stroked my wife's legs.

"Yeah, it was supposed to be pleasurable, but if it's only painful, take it off."

I paused, looked back at Anna, then back at my wife, who was trying to slip the contraption off her without unbuckling.

"You two can share the vibrating set. Anna now, and Amanda later."

That gave both girls a pause. They both knew how short their dresses were, and going commando was a recipe for them flashing their clams.

The rest of the drive was silent. At the restaurant we parked, and just like earlier, I put a girl on each arm on the way in.

My early reservation plus a 20 in the hands of the maitre d (yeah, it was the offseason) meant that we got the type of seating I wanted: A round booth.

I don't think either girl realize the possibilities of this table, but I did. I motioned for Anna to sit first, and then Amanda behind her.

I slid in the other side, all the way in until my hip nearly touched Anna's.

"Amanda, be a dear and slide around."

My wife did as I asked. Keeping her body close to the table so as to not to stand up and draw attention, she swiveled her hips around the table, into the other side of the booth. Halfway around, she realized that this position exposed her nearly bare backside and pussy to the world, and her hand whipped around to push her skirt down.

Since I was facing the room, I could see that several pairs of eyes were locked on our table and caught my wife's show.

I met eyes with one distinguished-looking gentleman a couple tables over. He nodded his head in salute, and I did the same, then took the opportunity to lean over and kiss my wife deeply.

When we released, I turned towards Anna. Correctly predicting the look of disgust on her face, I instead pressed the remote button, and watched her eyes widen in surprise and pleasure.

The restaurant was a higher-end steakhouse. As I expected, the wait-staff was exclusively male. Our waiter was Mediterranean, dark, curly hair and swarthy skin. He looked to be about thirty, and I was sure he had quite a few notches on his bedpost.

When he arrived at our table, I could see his eyes light up at these two gorgeous twenty-something in scantily-clad attire. I could see him looking around the table, trying to figure out which girl was mine and which wasn't. He was probably planning to turn on the charm and see if he could get a set of digits for later.

Unfortunately for him, I was feeling possessive, and I ordered wine for the table without either of the girls giving input. Not that either was really capable.

Amanda had become quite shy since she had mooned the restaurant, a fact I pointed out to her, along with several of her admirers.

Anna was normally quite engaged and authoritative, but she was currently focused on the sensations in her pussy which I had triggered as the waiter approached.

It wasn't until he left and I switched it off that she blurted out "ohmigod" and took a sip of water.

I chuckled now, enjoying the redhead's discomfort.

I repeated the trick when the waiter returned with the wine, though this time Anna was able to blurt out a "Thank you" when her glass was poured.

After two trips with not even eye contact, the waiter left, clearly confused.

I shut the vibrator off again, and leaned over to my wife's friend.

Slipping my hand up her skirt and into the thong she wore, my finger checked her pussy for wetness as I whispered in her ear:

"Which would you prefer, to cum now, here, in the middle of the restaurant, or wear it through the meal. I would only turn it on intermittently, and never let you get close to cumming."

Anna bit her lower lip. I could see her willpower crumbling. I had been playing with her body since lunch, but not let her cum since our tryst in the bathroom. I was sure I had almost broken her defenses.

"I-i want to cum." Her voice was small and unsure, not like her usual self.

"What was that?" I asked.

"I want to cum."

"Ask nicely."

"Let me cum. Please let me cum."

Hmm, well, just so you know, if you choose to cum now, Amanda will have to wear those panties all meal, while you are left to... air out. Are you going to do that to your friend?"

Anna nodded now.

"Look at her, Anna. Look at her and say it."

Anna looked up at my wife. Amanda stared back, eyes wide. She knew what I had said, and looked terrified.

"Sorry Mandy. But I-I need... I can't do it anymore."

Now up to this point, Anna had only apologize for attempting to rip the phone from my hands last night, but never for her transgression that landed her in this predicament.

Leaning in closer, I spoke very low, but forcefully, so that only Anna would hear me.

"So, you cunt, you apologize to your friend for pleasure, but you won't apologize to me for nearly breaking up my marriage."

I didn't give her a chance to respond, just hit the remote to turn the vibrator on full blast.

To this point, we had only run it halfway, so when it went full-bore, even buried between Anna's legs under the table, it was visibly audible, like a cellphone.

Anna's hands gripped the edge of the table as her pleasure overtook her. To her credit, she didn't make a noise, though with her eyes closed, biting her lips, head thrown back, it was fairly obvious what was happening.

When she finally exhaled, indicating her orgasm was finished, her hand reached out, slapping my arm. I turned the vibrator off, and Anna inhaled deeply, finally catching her breath.

"Go to the bathroom and clean yourself up. Take your panties off and bring them back."

Her relief was visible, and Anna nodded and rushed out of the booth.

Amanda inhaled sharply, and I turned to see that Anna's excretions has left a damp spot on the back of her dress.

I bit my hand to keep from laughing.

The waiter returned again, this time to take our food order.

"Where is your ..." He said, motioning towards Anna's place.

"In the bathroom" I replied, cutting him off. I knew he was trying to get me to indicate our relationship, but I ignored him.

I ordered food for all three of us and sent him on his way.

Anna returned a few minutes later. She had discretely folded up the thong and carried it, and she now slipped it to me under the table.

Amanda had her purse with her, so she stuffed the thong in her purse and took her own trip to the bathroom.

Anna had done her best to clean up, but the smell of pussy does not dissipate easily, and it found its way back to the booth with her.

My hand slipped under the table and onto Anna's leg, but when I approached her pussy again, she blurted out:

"Please don't."

Surprised at her challenge, I replied "Why shouldn't I?"

"I-I'm still close. And if I cum again, I will ruin this dress."

I could hear her honesty in her voice, so I decided to change the subject slightly.

"Anna, have you ever worn a buttplug?"

I saw her face screw up, and she shook her head no.

"Never. Not even during sex?"

Again, a no.

"Hmm. But you have been fucked back there."

This got a nod.

"DP?"

I got a shrug as a response.

"What does that mean?"

"I was on top of a guy and he stuck his finger in my ass once. Another time, Amanda used two dildos on me at the same time."

Her confidence was returning now. She did enjoy using her experience, particularly with my wife, against me.

Our conversation was broken by my sighting of Amanda returning from the bathroom.

I wondered the range of the remote, so I pressed the button. The range wasn't good, because my wife kept walking towards us. About 20' from the table I saw her pause, and suddenly her eyes became very big. I turned off the vibrator, and she continued her walk back, though it was less a strut and more of a skulk.

Sliding back in the booth, both hands on her skirt to hold it down, she slid in next to me.

"Ohmigod" she whispered, clearly uncomfortable.

"Amanda, Anna and I were just discussing her experience with all things backdoor. She said you once put two dildos in her at once?"