📚 cherry Part 3 of 7
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Cherry Ch 03 Fun With Friends

Cherry Ch 03 Fun With Friends

by raiderzgirl
19 min read
4.69 (4700 views)
adultfiction
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I spent the night with Alex in his hotel room, and neither of us got any sleep. Every time I was sure that we were done, it would begin again. We couldn't stop. His stamina was impressive, I knew that much even with my tragic lack of experience. He seemed to never tire of licking my pussy, and I absolutely loved it. I finally understood what all the girls were raving about back in college.

He encouraged me as I went down on him too, giving me tips to make it the most enjoyable it could be. When he finally finished in my mouth I thought I would cum too, just from the sheer eroticism of the moment. He told me that I was "a natural," and I was quite pleased with myself.

The next morning was Saturday, and Alex told me he had a 7:30 a.m. breakfast that he had to attend prior to the other convention activities. I knew he must be exhausted, but he told me that the night had been well-worth his lack of sleep. I had to agree. I started to get up to get ready to leave, but Alex stopped me.

"You don't have to work today, do you?" He asked.

"No, but you're going to be busy all day so I just thought..."

"How about if you stay here and order some room service, then get a few hours of sleep. I'll blow off the afternoon, come take a nap with you, and then we can do whatever you want." He smiled, then added, "In or out of bed."

I laughed. "Okay, if you're sure."

Alex nodded. "Oh, I'm sure. I want to get as much of you as I can before I have to go home."

With that, he took a quick shower and planted a kiss on my lips as he headed out, looking delicious in his dark grey suit. I wondered how much he would tell his accountant friends about the night we had shared, but quickly realized that I didn't really care. If I had had any friends, I would most certainly be spilling all of the juicy details to them.

A housekeeper knocked on the door, and I let her in to clean the room while I waited for my breakfast to arrive. I knew she could smell the lingering scent of sex in the air, and the naughty thought made me smile wickedly to myself. I sat on the couch and turned on the TV while she hummed a happy tune and changed the DNA-covered sheets.

When she was gone, I ate some fruit and a bagel, took a hot shower, then crawled naked between the soft, freshly laundered sheets, willing my mind and body to relax.

However, sleep was not in the cards for me that morning. Every time I closed my eyes I saw Alex's head between my thighs, his face when he climaxed, his smile just before he buried his cock inside me. I found my hands wandering down my body, squeezing my breasts and teasing my nipples the way Alex had done. My left hand remained there, making my nipples rock hard, while my right hand continued down. I spread my legs, letting out a deep sigh as I started touching myself.

Jake had told me early in our relationship that masturbation was a form of infidelity. He believed that any sexual act taking place without your partner present was cheating. I took him at his word, and never once throughout the course of our relationship did I attempt to pleasure myself. Even at the end, when he never touched me. Ironic, that he ended up fucking who-even-knows-how-many people, while I remained loyal to the point of never having an orgasm. After I left him, I was so focused on succeeding that I put everything else on pause. It had truly never occurred to me that I was single, and I should be having sex, or at least getting myself off, on a regular basis.

Laying there in Alex's hotel room, my fingers rubbing lazy circles on my clit-tender from all of the night's activities-it occurred to me how much I had missed out on. By this time I was 26 years old. Most people my age had experienced so much sexually. Experimented, discovered their likes and dislikes, learned how to please their lovers. I felt so robbed, so incredibly cheated.

I reflected over the past 12 hours and smiled as I thought of all that had happened. I gave myself over to the sensation between my legs and listened to my body. I felt my pussy get wet, and responded by sliding two fingers in, and then rubbing my swollen clit. Slowly at first, then harder and faster. I moaned as I brought myself closer and closer to orgasm. I felt the excitement of depriving myself when I stopped.

My imagination started to run wild. What if I was driving someone crazy with my mouth at the same time that someone else was driving me crazy with theirs? What if I had the amazing sensation I felt when Alex was behind me, driving his cock into me and fingering my ass, but I was making someone else cum with my mouth at the same time??

By the time Alex came back to his room after lunch, I had fingered myself to three orgasms and counting. I didn't even stop masturbating when he came in and started removing his clothes.

Alex chuckled as he crawled into bed beside me, naked and already growing hard.

"Hey beautiful. Did you get any sleep?"

"No," I breathed as he began kissing my neck and chest.

"Whatcha thinking about?" He asked as I continued fingering myself. He played with my tits, squeezing them and teasing my already-hard nipples.

"Mostly you." I inhaled sharply as he pinched my right nipple between his fingers.

"Mostly, huh?" he said, as his head dipped down and his tongue flicked across one nipple, then the other. "What else?"

I reached over to begin stroking his cock with my left hand while my right hand remained between my legs. "I was thinking," I answered, "that it could be fun if someone else were to join us."

"Mmmm, that could definitely be fun. You have anyone in mind?"

"No," I answered. "But I found you, I'm sure I could find someone else."

Alex chuckled. "Actually, I found you. But yes, I'm sure you could get just about anyone in this town to fuck you. Are you thinking a man...or a woman?"

I sat up and started moving down his body as I answered. "A man. For starters." I smiled at him as I circled the head of his cock with my tongue.

Alex closed his eyes and took a deep breath before answering. "A few of my colleagues watched us leave the bar together last night. I have a feeling any one of them would be willing to step up and help."

"I stopped licking him long enough to answer. "That wouldn't be weird for you?"

"Nah," he replied. "I only see most of these people once a year, if that."

I took my time, slowly stroking up and down the length of his shaft, licking my way up to the tip and back down again before taking him into my mouth. I loved the taste of him, and I loved the feeling of control I had when I went down on him. Soon his hands were in my hair and he was moaning as I stroked and sucked him toward orgasm.

I could feel myself grow wetter as I thought about him cumming in my mouth again. I wanted to taste more of him. But he stopped me before he reached that point and told me to flip around. "Get on my face, baby. I want to taste you, too," he said.

I was thrilled to try another new thing, and gladly straddled his face. His tongue dove into my wet depths as I leaned forward to resume servicing his cock.

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His hands were gripping my ass, encouraging me to grind myself against his face. He had not shaved that morning, and the stubble on his face felt amazing against my sensitive flesh. I moaned as he began teasing my asshole with his finger. I reached down to gently rub and squeeze his balls, making him moan in return. We both quickened our pace, each wanting to make the other cum. My hips were moving at a frenzied pace as he licked and sucked my clit. I knew I was getting close, and when the finger that had been teasing my ass slipped deep inside my tight hole, the waves that were looming finally crashed over me. I felt the hot liquid pour out of me and down his face as my entire being became consumed with the mind-blowing sensation spreading through my body. I tried to continue pleasuring Alex, but I was too lost in my own chaotic and overwhelming release.

Soon Alex was gently nudging me off of his face. I rolled over and lay on my back, my head toward the foot of the bed. Alex immediately moved between my legs and plunged his cock deep inside me. My body was still experiencing aftershocks of pleasure as he began fucking me, and I knew my pussy was tightening up around him. He drove himself into me, deeper than he ever had, harder and harder as he neared orgasm.

I wanted to watch him cum.

Through my moans of ecstasy, I managed to convey my wish by saying "Alex, cum on me..."

After a few more deep, hard pumps, Alex withdrew from me. On his knees between my legs, Alex stroked himself for me and within seconds I watched as rope after rope of hot jizz erupted from his cock and landed on my stomach and tits. He roared as he came, "Oh fuck baby!" It was by far the most arousing thing that I had ever seen in my life.

My body had barely finished quaking from my own unbelievable orgasm, but watching that happen-and seeing his huge load of cum on my tits-had me immediately wanting more.

I knew he would need a few minutes to recover, so as he collapsed beside me I reached down to rub his jizz on my nipples, then brought some to my mouth, savoring the taste. Alex seemed to be mesmerized, watching as I delighted in playing with the load of cum he had deposited on my body. I had already started rubbing my clit, but Alex came up onto an elbow and reached down to take over. He slid two fingers deep inside my pussy, getting them slick and wet before rubbing hard circles in exactly the right spot. Within minutes I was writhing with yet another amazing orgasm. Alex placed his palm so it kept pressure on my swollen clit, then slipped his fingers back inside me so he could feel me cum, exploring the walls of my pussy as I tightened up and convulsed with pleasure.

We were both quiet for a moment, and I hoped he wasn't disgusted by what I had done. When my eyes met his, I knew I had nothing to worry about. He gave me a wicked grin and said "Goddamn woman, you are so fucking sexy!"

I laughed. "Thank you sir. I believe you bring it out in me."

Alex held my gaze. "No...no, it's all you sweetie."

He leaned in to kiss me, then went to fetch a warm washcloth. He returned to the bed and gently cleaned the mess from my skin. He tossed the washcloth on the floor and got into bed, this time with his head on the pillows. I crawled up to cuddle, and he held me close. Soon his breathing slowed, and I knew he was sleeping. I stole a quick glance at his handsome face before returning my head to his shoulder and finally falling asleep.

**********

Alex and I slept in each other's arms all afternoon. I awoke to his hand teasing my nipples.

"Mmmmm...." I smiled and opened my eyes to find him watching my face. I hoped I didn't look too terrible. I immediately reached up to smooth my hair.

"You still look beautiful," he said, as if reading my mind.

I laughed and rolled my eyes. "Oh, I'm sure."

"Now," he said, "as much as I would love to fuck your brains out right now, let's discuss your idea from earlier. I'm definitely intrigued."

"Okay," I began, indulging in a long stretch before continuing. "So...I had this friend in college, Sarah, and she used to tell me details about her sexual escapades. One day she told me that she had been with two guys-her boyfriend and a guy they met at a party. She said it was the hottest thing she'd ever experienced. At the time, I didn't think it was anything I would ever even consider doing. But now..." I smiled and wiggled my eyebrows.

Alex laughed. "Well I would love to help you make this fantasy a reality. You should probably know that I have never been in a threesome either, but I'm definitely game. As long as you don't want me and the other guy to..."

I looked at him questioningly for a moment before realizing what he meant.

"Oh, no," I replied. "I want all the attention on me!"

Alex laughed. "Well then," he said, getting up from the bed, "Let's get cleaned up and head down to the casino to find you a boy toy!"

We got in the large marble shower together and soaped each other up for far longer than was necessary to get clean. Alex called down to the front desk to have a toothbrush brought up for me. The only clothes I had were what I had arrived in, so I left my jacket off and went with just my skirt and dress shirt. I left one more button undone than I normally would, and I left my panties behind altogether. I had no makeup other than the powder compact and lipgloss from my purse, but Alex assured me that I didn't even need that.

Alex shaved and got dressed in dark jeans and a royal blue button down. He looked gorgeous. We left the room and headed downstairs.

In the elevator, Alex asked what type of guy I was interested in.

I thought about it for a moment. "Nice looking, clean, not too skinny...taller than me." I paused briefly before firmly adding "Single." I would not play a part in anyone else's infidelity, knowing firsthand how it felt to be on the receiving end of that devastation.

"That's it?" Alex asked.

"Yeah," I replied. "Beggars can't be choosers." I smiled up at him.

He laughed at that. "You are most certainly not going to have to 'beg' for anything, sweetie." The elevator doors opened and we stepped out. "Now, let's go to the bar, because there is someone I would like for you to meet."

Surprised, I turned to Alex with wide eyes. "You already found someone?!" I shrieked. I was suddenly nervous.

Alex took my hand and chuckled. "Relax. This is gonna be fun. And to answer your question, I may have sent a quick text to one of the guys who was at the bar with me last night. I've known him for five years, and we keep in touch sporadically. We usually try to fit in a round of golf while we are here for the convention. He's a good guy, but he's had a tough time. Hasn't dated since his wife passed away two years ago."

"Oh...how sad."

Alex continued, "I thought maybe he can help make your fantasy come true, and you can help boost his confidence so he can get back out there."

"Okay." I took a deep breath as Alex led me toward a handsome man standing by the bar. He looked to be around Alex's age, 35 or so. He had dark blonde hair, nicely styled, bright blue eyes, and a well-kept beard.

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"Hey, Ross! Meet my good friend, Cherry." Alex was beaming.

"Cherry, so nice to meet you," Ross said has he took my hand and kissed it softly.

I giggled. "Likewise, Ross. That's my favorite name, by the way."

"No way," Ross replied, smiling.

"Way," I said. "I have a very special teddy bear named Ross."

"Wow," he replied. "I'm going to pretend he was named after me and not the TV character."

We all laughed, and then ordered drinks. We found a table in the back of the room and made small-talk for a while. They caught up on the events of their lives since last year's convention, and I learned that Alex had a ten-year-old son named Jonah. Ross had eight-year-old twin girls, Sadie and Emma. I thought about how difficult it must be for him to be raising them alone.

"What about you, Cherry? Any kids at home?" Ross asked.

"Nope," I replied with a smile. "Just me, and I'm expensive enough."

The guys laughed politely, then Alex quickly changed the subject. I was grateful.

I ordered a second drink, which I hadn't planned to do, but I felt perfectly safe with Alex...and I thought it might not hurt to get a tiny bit tipsy. I needed the liquid courage, and it definitely helped.

I let my eyes wander over Ross while the men continued chatting. He was extremely handsome, and I loved his beard. I wondered how it would feel between my thighs. Pretty good, I bet...I smiled inwardly at the thought, and silently hoped I would find out soon.

My eyes dropped to his chest, and I could tell he looked good under his fitted black T-shirt. My hand moved to Alex's thigh under the table, and I gave it a little squeeze. When he turned to look at me I winked at him. I was fairly sure that Ross was aware of the exchange, but he said nothing.

"It's so loud in here," Alex announced. "Why don't we move this party upstairs where we can hear each other a little better? I'll order us a nice bottle of wine." He smiled, and got up from the table, and Ross and I followed suit. It wasn't very loud in the bar, but neither of us pointed that out.

Alex seemed perfectly at ease as he took my hand and led me back toward the elevator. He continued making small talk all the way to the room.

When we got inside, Alex picked up the phone and ordered a bottle of wine. He dimmed the lights and started some soft music. "This is better, huh?" he asked with a big smile. He moved to the living room area and took a seat on one end of the couch.

I sat in the middle, giving Ross the option of the other end of the couch or a chair facing us. I was happy when he chose the couch.

I had butterflies in my stomach, but I forced myself to act as nonchalantly as possible.

I turned my body so I was facing Ross just as a knock sounded at the door.

"That's the wine," Alex said cheerfully as he rose to answer the door.

"So," Ross said. "Have you known Alex long?"

I smiled. "You know the answer to that question, Ross."

His handsome face turned red. "Oh, yeah. Sorry. I guess I'm just a little nervous."

Seeing his nervousness somehow made mine vanish and give way to a new kind of excitement.

I reached up and touched his cheek softly, then gently scratched my nails through his beard. "No need to be nervous. We're gonna have a good time. Don't you think so?"

Ross smiled. "Yes...Yes, I think so too." I could tell he was having a hard time not looking down at my breasts.

Feeling frisky, I unfastened the next button on my top and watched his face. No longer able to resist, he looked down, then immediately back up.

I returned the favor by dropping my eyes down to his crotch, and was surprised to see a bulge already forming in his jeans. I raised an eyebrow at him and watched the adorable blush return to his face.

Alex returned, handing us each a glass of wine and making a toast to new friends. I thanked him and tried a sip; it was delicious. I took another, much longer drink before standing up and placing my glass on the side table. My nervousness was long gone, and I was ready to start living out the fantasy I didn't even know I had until that morning.

Alex had returned to his side of the couch and was leaning back, looking quite relaxed. He had a mischievous grin on his face, as if he couldn't wait to see what was going to happen next.

Ross took a long drink of wine, then set his glass aside, trying to look as comfortable as Alex clearly was.

I looked back and forth between the two of them as I kicked my shoes off to the side of the room. They were both so great-looking, in such different ways. Alex, sexy and intense with those dark eyes, and Ross, wholesomely handsome and all-American. Both beautiful. And I was about to have them both. With that thought, a surge of excitement spurred me on.

Remembering how Alex drank in the sight of me the night before, I decided to stick with that tactic. Both men watched me as I untucked my top and unfastened the last of the buttons. Their eyes were glued to me as I dropped the shirt to the floor. I decided to mix it up and get some participation from my captive audience.

"Alex," I said, "can you help me with this?"

"Of course." He stood up and moved behind me. His fingers made my skin tingle as he unhooked my bra and slid it off of my body. I watched Ross, no longer trying not to stare as my bare breasts came into view.

Alex dropped my bra to the floor and reached around me to give them a squeeze, but only for a moment. He obviously did not want to deprive Ross of the view. He reached down and unzipped my skirt, and it fell to my feet, leaving me naked. I kicked it aside.

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