Best Friends: Ali’s Adventure

Gretchen and I met at her apartment on the night before we left for our conference. We had decided to ride to the airport together, so I packed my bags and went over. We had not really seen each other, except at work, since the Onaspa. And I was excited she was going with me to this conference. Most advertising conferences can be boring, and I was looking forward to a few nights of cunnilingus and masturbation with Gretchen. I knocked and she opened the door of her apartment dressed in only a pink robe and matching slippers.

"Alison!" Gretchen said as she hugged me.

"Hi, sexy," I said. We kissed softly and she dragged me inside. Once the door was closed she took off her robe and put in on a hook next to the door. She was naked of course. I followed her to her couch. She told me I could get naked if I wanted to. So I removed my clothes and sat next to her, and talked for a bit. I told her how I had hoped we could share a room at the conference, but our boss assigned us rooms and I was stuck with Grace Jensen. Grace was around 45 years old with a hunky husband, three kids and a big house. All the other women at work hated her. She had the "dream life." So I wasn't looking forward to sharing a room with her. Gretchen got stuck with one of the younger women from the office, Angela Po. She was a bubbly 23 year old Asian girl. Gretchen joked that she would at least have a better view in her room. We chatted about work for a while. I got bored so...

"Do you want to fool around some tonight?" I asked

"Of course," she replied, sliding up to me. We kissed for a while. Then we got into a 69 on the couch. I just love eating pussy and she tasted great, so I enjoyed every second. After we were done, she asked if I wanted to use some of the new toys she picked up at the Onaspa. I said yes. So we went into her bedroom and she brought out a selection of toys; including butt plugs, dildos and a strap-on. I picked up one of the butt plugs (it was rather slim and about 6" long with ridges along the sides) and asked for some lube. Gretchen said she would lube it up for me and insert it if I wanted. I said, "That would be wonderful."

So she took the toy from me and went over to her dresser and grabbed the lube. She told me to bend over the bed. I felt extremely exposed as I placed my hands on the comforter and spread my legs. Gretchen gently rubbed lube on my butt. Slowly, she inserted the plug. Wow, did it feel great, each ridge sent waves of pleasure up my spine as she pushed the plug further inside. Once it was all the way in, my pussy was dripping and I was breathing really hard.

"Don't move, honey," she said as she grabbed the strap-on from the bed. "I didn't get a chance to use this at the Onaspa. But I am told it feels awesome." The dildo on the harness was realistic and about 10" long. There was a control box mounted on the harness that she said made it vibrate. She put the harness on and stepped up behind me. Like with the butt plug, she slowly worked the dildo into me. But after a dozen thrusts, she started to fuck me really hard. Then she turned on the vibration, and I went wild. "Fuck me Gretchen,' I screamed "Fuck my pussy." She picked up the pace even more. The combination of the butt plug and Gretchen's thrusts sent me over the edge. The sound of her hips slapping into my ass and my moans filled my ears and reverberated off the walls. I came really hard several times before I made her stop. We were both panting very heavily and our bodies were slick with sweat.

We rested for a few minutes, before I offered to return the favor.

."Sure," Gretchen said. And she took of the strap-on and chose one of the butt plugs (this one was wider without ridges and had a vibrator inside it.). I got myself into the strap-on harness. I told her to lie down on the bed and pull her legs up to her chest. Then, I lubed up her anus and the plug. As I slowly inserted the plug, I licked her pussy, just like Lydia did to me at the Onaspa. Gretchen loved it.

After a few minutes I had the plug fully inserted in her ass, so I stood up and climbed onto the bed. I attempted to insert the dildo into her pussy slowly, but since I had never fucked a woman with a strap-on before, I slid the whole thing into her in one thrust.

'Oh, my fucking God!" she screamed.

"Sorry," I replied.

"Don't stop,' she commanded. "Keep moving."

I started to thrust my hips towards her. She in turn grabbed the remote to the butt plug and turned the vibration on. Her moans got very regular, she urged me to fuck her harder. The combination of my thrusting and the plug that was still in my ass started to bring me towards an orgasm as well. Gretchen's hands slid their way up my hip and her right hand found the control box to the strap-on. She must have turned the thing up all the way, because I felt a sudden rush of vibration on my clit. Soon we were both moaning loudly and my thrusts became more forceful. I don't know how long we fucked like that, but when we both came, I just laid there on top of her and panted. My thighs burned and my arms felt like jelly.

"What a work out," I said. "Now I know why guys can't move afterwards."

"Ali," she pleaded. "Can you...turn...off the strap-on...please? Oh my god...I'm coming again." Her body writhed in pleasure and I pushed myself up and withdrew the vibrating, plastic cock from her.

"Thank you," she breathed. "Wow, I love that thing, but wow."

I took off the strap-on and removed my butt plug. Gretchen removed her butt plug as well and took all the toys to the bathroom to clean them. "That was fun," she said when she came back into the room. I was still lying on the bed, rubbing my hips. She cuddled up next to me and within minutes we were asleep.

It was about midnight when I woke up. I had a very urgent need to pee. So I stumbled to the bathroom, relieved myself, washed my face and went back into the bedroom. Gretchen looked so beautiful. Her blonde hair lay in a halo around her head. Her breasts were peaked with light brown nipples and they jiggled slightly as her chest slowly rose and fell. I sighed, turned off the light and climbed back into bed. I curled up next to her, cupped one of her breasts and fell asleep.

Back to the Airport

I was the first to wake up to her alarm. I shook Gretchen and she reached over me to turn it off. As she did, her right breast caressed my cheek. I turned my head and sucked her nipple into my mouth. She grunted in surprise. I released her nipple and she sunk back down into the bed.

"We have to be at the airport in three hours," she said.

"That long, huh. Oh my, how are we going to pass the time?" I jibed.

"I know one way," she said, her head disappearing under the covers and kissing my stomach. Soon we were in a sixty-nine. I really loved the tasted of her pussy. I don't think I could ever get tired of it.

After we came a few times we went and took a shower together. Gretchen brought the strap-on and the plugs so we could clean them as well. And since the strap-on was there, so...I took the opportunity to bend her over and fuck her in the shower. It was very intense. The combination of the hot water, her moaning and her slick skin made it very erotic. I almost wish there was video of it. After she came, we cleaned the strap-on and went to the kitchen for breakfast. Gretchen decided to return the favor, so she crawled under the table and went down on me. After my delicious breakfast we had just enough time to put on our clothes, do our make-up and hair and pack some sex toys for the trip, including the strap-on and lube. Then it was off to the airport.

The cab dropped us off at the front and we made our way to the concourse. As we walked up to the security checkpoint, we saw Grace and her husband embracing. Grace is a tall voluptuous woman with red hair, freckles and a bit of a belly. Her husband really was a hunk. He looked like Harrison Ford, except his hair was dark black with a sprinkling of grey and he had a small silver-grey moustache. I definitely would spread my legs for him. "Damn, he is fine," said Gretchen.

"Oh yeah," I said. "I wonder if he has a younger brother."

We both giggled. Grace pulled back from her man and looked our way. Gretchen waved. Grace waved us over.

"Morning, girls," Grace said. "This is my husband, Harry. Harry, this is Alison and Gretchen."

"Good morning, ladies," said Harry, he had a deep resonant voice that made my pussy twitch. God, did I hate Grace. "Well, baby. I got to get to work. Call me when you get in to the hotel." He leaned over and kissed her. They hugged and he walked off.

"So, we have about an hour before the flight boards, so do you want to get some coffee?" Grace suggested.

"A latté sounds wonderful," I said. So we grabbed our carry-on bags and made our way over to the coffee bar.

Nothing really happened until we were already in the air. Gretchen got up after the seat belt light went off to use the bathroom. When she came back she handed me something as she past my seat in the aisle. When I looked, I found it was her little black thong. I quickly put it in my pocket.

When I went to the bathroom, I pulled out her thong and examined it, stretching it with my hands. Then I took off my jeans pulled my white cotton panties off and kissed the crotch, which, because of my lip stick, left a perfect little lip mark on them. I balled up the panties. I exited the bathroom, walked past my seat, leaned over and whispered, "Thank you for the gift, let me repay you." I handed her my panties. She looked at them, smiled and laughed. Grace was listening to her iPod and reading a novel, but after the laugh, she looked over at Gretchen (they were seated next to each other); Gretchen quickly hid the panties. Grace raised her eyebrows and went back to book.

Several hours later, we grabbing our bags at the airport and catching a taxi to the hotel. When we got to the hotel, we checked in and went to our rooms. Our rooms were right across the hall from each other. Grace and I had a wonderful room with a view of the city. After I had put my clothes in the closet and freshened up a bit, I told Grace I was going to see what Gretchen's view was like. Grace said she was going to call Harry and take a nap. I walked across the hall and knocked on Gretchen's door. She opened the door and let me in. Her room was a lot like ours. I sat on the bed while Gretchen put some of her stuff away. Then she joined me on the bed. We talked for a bit, and then Gretchen leaned over and kissed me. I kissed back. Our hands started to roam all over our bodies. Right as it was getting good, we heard the door open. We had just enough time to break apart when Angela Po came in followed by a bellhop and her luggage.

Dammit, I thought. "Hi Angie," I said. "How was your flight from Boston?"

"It was hell," she replied. The bell hop set her luggage in the room, Angela tipped him and he left. And for twenty minutes we heard how horrible the trip from Boston was for her. I like Angela, but man, can that woman complain. During the conversation, we decided to go get dinner around 6 o'clock. Since it was almost four, I told them I was going to go tell Grace and take a shower.

When I unlocked the door to the room, I heard a soft moan from inside. I slowly walked into the room. The lights were off, but enough light was coming in from the shaded windows that I could still see ok. Grace was lying on her stomach in her bed and under the blankets. Her ass moved slowly up and fell down. I knew immediately that she was masturbating. I stood there next to the bathroom for five minutes, listening to her moan and watching her hips rise and fall. Her motions quickened until she came. Then I slowly stepped back to the door, opened it and said, "Grace, are you up?"

She jostled around a bit and replied, "Yeah, um, what's up?"

"We were going to go to dinner soon. Do you want to join us?" I asked. I walked into the room all the way and turned on the lights. She was lying on her back; the covered were bunched up around her chin.

"Sure."

"I'm going to take a shower," I said as I slowly removed my clothes. Grace watched as I removed my shirt and bra. I stayed facing her as I unbuttoned my jeans and kicked off my shoes. I had forgotten that I had given Gretchen my panties, until the cool air of the room brushed my pussy. "We were planning to meet up around six, so there should be time for you to take a shower, if you want."

"Sounds good to me," she said. Her eyes wandered from my face down to my pussy. It was exhilarating to be naked in front of her. I turned to retrieve my toiletry bag, which was on the floor in my carry-on bag. I opened my legs slightly and bent over, giving Grace a nice view of my ass and pussy.

"I promise I won't take long," I said and walked into the bathroom. The shower was just what I needed. It was hot, and the showerhead had a massage feature. I didn't masturbate, although I wanted to. When I came out the light was on. Grace was standing over her suitcase getting out her own toiletry case. Her ass was very round with the cutest dimples on the cheeks. Freckles covered her whole body. When she turned, I got to see her front. Her breasts sagged slightly and she had very large pink nipples. Her pussy was trimmed, but the bright red hair with a few sprinkles of white drew my eye right to it.

"All yours," I said, as I walked over to my suitcase. When she passed me, I took the opportunity to check out her ass again. Wow, she even walks sexier when she's naked.

I checked the time as I heard the shower start up again, 4:30. I grabbed my clothes walked over to the bed. I put on a short blue skirt, a blue bra and a blue silk blouse. I decided not to wear panties again. I put on my make-up in the mirror across from my bed. I was brushing my hair when Grace came out of the bathroom. Other than the towel around her hair, she was naked. I watched her from my bed as she dressed. We talked about restaurant choices, and she asked me to help her choose clothes. The whole time I drank in her body. I followed her breasts as she bent over to choose her underwear. I stared at her ass as she pulled her panties up. I was being so bad, and as I felt my pussy moisten, I realized I might need to put some panties on. When Grace went into the bathroom to put on her make-up, I wiped my pussy with my old panties, quickly took out the matching panties to my bra and put them on.

When we were ready, I called over to Gretchen and Angela's room. At first I didn't get an answer, and when I called back Gretchen answered. She said they were almost ready and to come over. We found the door ajar when we crossed the hall and the two of them were in the bathroom doing their hair. We chatted for a while and decided to ask the concierge for a good sushi place.

We made our way to the lobby and talked to the concierge, he was a really hot Latino man named Ramón. He called us a cab and we were off to the sushi place. Dinner was great, the sushi place had a bar, and so after we ate, we went to the bar for drinks. We talked about work for a while, but after a few drinks Gretchen asked Grace where she met her husband. Well actually she said, "Where did you get such a fine looking Han Solo?"

Grace looked surprised. She stammered a bit, and then said, "At a party, when I was in college. I was dating one of his frat brothers, and after that went south, we started dating. And as they say, it went from there."

"Does he have a brother?" asked Gretchen.

"No, just a sister," said Grace.

"That might work, if she's as hot as Harry," said Gretchen.

"What?" Angela and Grace said in unison.

I started laughing, and that caused Gretchen to laugh which caused the others to laugh. I asked Angela if she had a boyfriend.

She said, "No, men are too needy, and I don't have time for one."

"Maybe Grace should set you up with Harry's sister?" I said.

We all laughed again. After another round or two, we decided to head back to the hotel. When we arrived back, we heard dance music coming from the hotel bar. Angela lit up.

"We should dance for a while," she said.

"That sounds great to me," agreed Grace.

"I will be there in a few, I need to hit the little girl's room," I said.

"Me, too," said Gretchen.

Angela and Grace headed to the bar, and we went to the restroom. I went into a stall to pee; Gretchen went into the one next to me. After I finished, I heard a gentle tap on the door. "Can I come in?" I heard from outside. It was Gretchen. I undid the latch and she came in, closing the door behind her. Her hands grabbed my head and she leaned down for a very passionate kiss. As she stood up, she said, "We should head back to one of the rooms soon. I want to taste you again." With that she exited the stall. We washed our hands and went back to the bar. Angela and Grace were dancing with some guys when we got back. Gretchen pulled me on the dance floor. Soon, we were dancing with some guys, too.

Ramón, the concierge came in. He started to dance with Angela. Gretchen moved up behind them. It was sexy. The guy I was dancing with leaned in and asked if I wanted to go up stairs with him, his name was Paul and he was not what I was looking for that night. I politely said no. He seemed ok with it, but after the song was over, he went to dance with some blonde in a red dress. Grace had moved over to a table and was sipping a drink.

Gretchen gave me a nod and I knew it was "time to leave." I walked over to Grace, and asked her how she was doing. She said she was fine, just taking a break. Gretchen stumbled over next to us. She seemed to be a "little drunk".

She said, "I am feeling a little dizzy. I think I am going to go upstairs."

"Let me walk you up. I think I am ready for bed, too." I said.

"Night," Grace said, and we left.

We were going to use Gretchen's room, but when she looked in her pockets, she didn't have a key. So we went into my room. As soon as the door closed our hands were all over each other. Then we moved over to my bed. I pulled her pants off as she undid them and we fell into my bed. Lydia pushed up my skirt and we moved into a 69. We only had a limited amount of time so we worked fast, both of us came quickly. Then Gretchen and I went down to the front desk to get a new key, so she could get into her room. After we got the key, we went by the bar again. Angela and Grace were still dancing so we went back up to Gretchen's room. I hiked up my skirt and took off my panties. Gretchen removed her clothes and pulled out the strap-on. She bent me over and fucked me hard and fast. I came really quickly, but before we could switch we heard Grace and Angela singing in the hall. Gretchen tossed the strap-on into her luggage and I dropped my skirt. Gretchen grabbed her robe and ran into the bathroom.

I didn't know what to do so I just stood there. Angela came stumbling into the room. Looked around and said, "What're you doing here?"

"Gretchen's in the bathroom, she started to feel sick so I stayed in here with her." I replied.

Just then Gretchen flushed the toilet and came out looking well worn and tired. "Hey," she said. "I think I am going to sleep now." She slowly walked over to her bed and took off her robe and laid down.

"Night guys," I said and I went to my room.

Grace was in the bathroom, so I started to take off my clothes. I realized then that my panties were still on Gretchen's floor. I took out a large t-shirt and put it on. When Grace came out she was wearing just a pair of panties. We talked for a minute, then I went to the bathroom and she went to bed.

Over the next three days, it went pretty much that way. Every chance Gretchen and I got to be alone we were fooling around. We would try to sneak away at lunch or leave early from dinner. We would go down on each other or masturbate together. The strap-on was only brought out when we knew Grace and Angela were at a seminar on art design or in a long meeting. Two days in, we had the Women in Advertising Panels and Luncheon. So, I knew Gretchen and I would not be able to get away for our afternoon meal. Instead, I started the day wearing my small vibrator harness under my panties. During the morning break, I gave the wireless remote to Gretchen, and for the rest of the day, she would turn it on at random times. God, it was great. All the sneaking around made every flutter and orgasm feel even naughtier.