Diane was flirting with me even more that the two nights before. The other night Scott was too drunk to notice Diane’s flirting. On this night she was openly flirting with me again and Scott didn’t seem to notice. At one point I looked over at her and she was rubbing a braless nipple under her thin white blouse. Only I could see what she was doing due to where she was sitting and the dark jacket that she wore over the blouse. She caught me watching but instead of pulling her hand away she continued to caress one nipple and then the other as she smiled at me. I looked over at Scott and he too was smiling at me. I had never done a three way before but it was beginning to look as if this might be the night.
My girlfriend was in Philly with her family for the holiday. Her parents didn’t like me. Maybe it was because I was divorced, twelve years older and fucking the life out of their princess. If they only knew what she would and could do in bed. Anyway I was free for whatever Diane and Scott had in mind for me.
I t was nearly 9:00 and I was starting to clean the bar in preparation for closing. Diane had gone to the lady’s room. Scott called me over looked me straight in the eyes and asked if I liked Diane’s tits.
“Sure” I said.
“Want to see more?”
The question left me speechless.
“It’s OK; I like to watch my wife getting fucked. Are you in?
“SSure” I stammered. My cock was starting to get hard already.
“Alright then. When you finish here come to our suite. The number’s 201. You OK, got any questions?”
“No, I’m good.”
At that point Diane was back and took her seat. While looking straight me and smiling she asked Scott, “Is he in?”
“Yes, darling he’s in.”
Diane’s smile got wider and she said, “Lovely.”
With that Scott signed the bar tab to their suite. Diane blew me a kiss and they headed for the door. When they got to the door Diane turned and gave me another smile and a blown kiss.
I turned around and Tom was watching from the dining room service window. Tom was the hotel’s night security guard. He was there to get his nightly double shot of Smirnoff and to walk me to the front desk with my cash deposit.
“She’s hot” he said as I was pouring his vodka.
“Yes, she is very hot and her husband is going to watch me fuck her”
Tom was incredulous, “No, you’re not.”
“Oh but I am. And you’re going to help me.”
“And what will my role be? Will I have to hold her down or just hold the husband back?”
“Nothing of the sort, your job will be to let me in the north door after I park at Denny’s.”
Only the main lobby doors can be opened from the outside after sundown. Tom would open the door from the inside to let me in. Company policy did not allow employees on the property outside of normal working hours. That is why I needed to hide my pick-up at Denny’s and sneak in the back door. Since all of the managers were at home on the holiday I still didn’t want to take any chances.
At 9:10 I started my truck and drove the service road to Denny’s. I parked, put my wallet under the driver’s seat and half jogged the 100 yards back to the hotel and the back door. Don’t ask me why I left my wallet behind. I just did.
When I got to the back door, Tom was waiting with the door ajar. “You lucky bastard” Tom said as I passed.
“Maybe, I’ll let you know how lucky tomorrow.” I said without stopping.
I got to the elevator and pushed the up button. On the second floor I made my way to their suite. I knew it was a suite from the number. Zero ones were suites. I knocked quietly on the door and Diane opened it almost immediately.
She was in a short black satin robe. I was guessing that she wore little else underneath.
She asked if I cared for a drink from the fully stocked bar. In addition to the bar with four stools there was a mini kitchen, and a sitting area with two large overstuffed leather chairs, a leather sofa and a coffee table. I said that I would have a Scotch and water. Diane told me to have a seat as she went to the bar for my drink.
When she returned and found me sitting in one of the chairs she said, “No, no sugar. You’re over here with me.” She held onto my drink as she sat on the sofa. I looked over at Scott. He just smiled and nodded. So I moved to the sofa for my drink and whatever else was to follow.
First the small talk. Scott wanted to know if I had a steady girlfriend.
“Yes, she’s with her family for the holiday.”
“How old is she?” Diane wanted to know.
“Nineteen.”
“Young. What are you, thirty?”
Thirty-one.” I answer.
“What is your take on older pussy?” Diane said teasingly.
By now I am loosening up. I had had a stiff drink at the bar and now I was half way through the one that Diane poured me.
“I never had any older pussy but I am always ready to explore.” I said boldly.
This brought a chuckle from Scott. The first sound he made since I got there.
Diane just smiled then took my Scotch and put it on the coffee table. Then she straddled my left leg and took my face in her hands and kissed me. At first two small pecks on the lips then a sensual kiss with her tongue deep in my mouth. As we broke the kiss I took a peak at Scott. He already had a hand inside his robe. Diane caught my look at Scott. She again took my face in both hands and directed my eyes to what was in front of me.
She undid the belt to her robe and let it fall open. She pulled it open even more to reveal a black lace babydoll and matching lace thong. When she leaned in to kiss me again, both of my hands went to her breasts and her hardened nipples. I caressed her nipples with my finger tips the same way she was doing it earlier at the bar. That’s when her hand went to my hardening cock.
I returned the favor by massaging her clit with my thumb. Her moans that followed told me that I was making her very happy. Again, I looked over at Scott. He now had opened his robe to expose his nakedness and was stroking his rock hard cock. Apparently I was making them both happy.
Diane got to her feet and uttered a single word, “bed.” I was on my feet in a flash. Diane took my hand and led the way.
Diane removed her robe and sat on the bed and went at my belt and zipper while I removed my shirt. With my trousers around my ankles I kicked off my loafers and removed my socks. I was now standing in front of this beautiful woman in just my boxers. Diane looked up at me with a smile and put her thumbs in the waistband of my boxers. She pulled the waistband out and over my raging hard cock and down to join my trousers. As she did this her cheek brushed the tip of my cock. She looked up at me and there was a drop of pre cum on her cheek. She smiled as she wiped the glistening droplet away with a finger. Still smiling, she put the finger in her mouth.
She lay back on the bed and pulled me to her. She put a hand behind my head and directed it to her gorgeous tits. I obliged by licking, sucking and tweaking her nipples. As I moved to lick her pussy she already two fingers buried in the wetness there. I did my best to stimulate her clit with my mouth while not disturbing her fingers. Soon she achieved what I hoped would not be her only orgasm of the night.
After she caught her breath she pushed me back onto the bed. I sensed that I was about to get a blow job. I was not disappointed. In a matter of seconds Diane’s mouth was pumping up and down on my cock. I closed my eyes and let her work my cock with her beautiful mouth. When she stopped sucking I opened my eyes. She had my cock in hand and continued to stroke it. She smiled at me and told me to relax and close my eyes.
When she resumed the sucking something felt different. I opened my eyes again to find that Scott was now sucking my cock. My first reaction was to push him away. But a blow job is a blow job, right? So this was the price I had to pay to fuck his beautiful wife. Diane watched me watch her husband suck my cock for a while. When she pushed him away and resumed sucking I again closed my eyes. I felt something wet touch my cheek. I opened my eyes to find Scott’s cock pointing right at my lips. Oh shit. He wants me to suck him.
It wasn’t like I had never sucked a cock before.
“No”
I was surprised. “What do you mean no”
“No, means no. I just wasn’t interested, OK?”
We were going to football camp early in the morning. Since we had to be out by 6:00am the plan was for me to stay over at his house. I could sleep in his room in his older brother’s bed. His brother was away at college. We showered before bed so that we could sleep late in the morning. We didn’t wear PJs to bed. Only me in my boxers and Greg in his jockeys.
We were watching ESPN. His not interested comment earlier was bothering me. I had to ask. “What did you mean that you were not interested?”
He waited to answer for so long that I thought he wasn’t going to answer at all. Finally he began to speak. “Bill, you’re my very best friend and I need to tell you something that I have never said to anyone before.”
“I’m gay or at least I think I’m gay” he went on.
I was speechless. I didn’t know what to say. I was thinking, how could it be. Greg was the best athlete in our school. He was all-county in football and the leading hitter on our baseball team. Now he is telling me that he is gay. All I could say was, “No you’re not. Why would you say something like that?”
“Because it’s the truth. Are you going to out me?” Greg said with a tear on his cheek.
Now my best friend, the star athlete, was starting to cry. I had to do something to make him smile and not cry. ”So” I said with a chuckle. “You mean to tell me that my best friend is a cocksucker?”
This brought a small smile from him. “Well, no, not yet anyway.” But I have thought about it a lot. “I would like the first cock that I suck be that of someone that I care a lot for. Someone like my best friend.”
“Whoa, what are you saying?”
“What I’m saying is that I want to give you a blow job. If you say no it’s OK. I’ll understand.”
Of course I wanted to say no to my best friend after he had just poured out the biggest secret of his life. Problem was my cock was beginning to harden with this talk. I thought about the prospect for a minute and asked, “What would I have to do?”
“Nothing, lose the boxers is all”
“OK”
“OK, are you for real?”
“Yes, now get over here before I change my mind”
Greg was beside my bed in a flash.
I lifted my ass to remove my shorts as Greg watched. He sat on the edge of the bed and gingerly reached for my hardening cock. It didn’t take long for me to achieve full erection. Greg had climbed onto the bed and began to stoke my cock in earnest. I had to admit that Greg was doing a better job than the girl who had given me the hand job earlier that evening. He had his hand inside his jockeys stroking his own cock as he played with mine. Then he pulled off his shorts to expose his raging hard on.
I had seen his cock many times in the gym showers. But now I am looking at his erect cock for the first time. I was somewhat disappointed to see that his cock was a bit bigger than mine. He moved to between my legs with my cock just two inches from his lips. When a drop of precum appeared he wiped it away with his thumb then kissed and licked the tip. I watched as he took a deep breath, opened his mouth and took my cock deep into his mouth. It didn’t take long for me to say that I was about to cum. Greg continued to jack and suck my cock.
Just as I was ready to cum he removed my cock from his mouth and watched as my cum shot out onto my stomach and chest. A drop of cum managed to hit his lower lip. Greg put out his tongue and licked it away. “Let me get a cloth” he said as he ran to the bathroom. A lot of thoughts went through my head while he was gone. I had little time to sort out my feelings before Greg returned with a warm washcloth. He sat on the edge of the bed and cleaned the cum from my chest and stomach. When he finished he stood and turned to the bathroom.
“Wait” I said as I grabbed his hand.
“What?”
I didn’t answer. I sat on side of my bed and put my hands on his hips and turned him until his cock was right in front of me. Without thinking, I took his soft cock into my mouth. It didn’t take long for his cock to grow to full erection. He pumped his cock in my mouth. Soon he announced that he was cumming. I let go of his cock with my mouth and took the cloth from his hand to catch his ejaculate. He took the cloth to the bathroom. I had my boxers back on when he returned.
Again Greg sat on the edge of my bed. “Thank you. Next time I’ll want you to cum in my mouth”
“Greg, there’s not going to be a next time.” “I don’t regret what just happened. Actually it felt good but I don’t want to do it again. I hope you understand.”
Greg nodded, his assent.
We stayed friends throughout high school but eventually we drifted apart. He is now living with his gay lover in Harrisburg. Sometimes when he comes home to visit his parents he will call me to join him for a couple beers. Once he brought his lover, Pete, along. Pete was a nice guy and he made Greg very happy. So I was happy for my friend.
Now Scott had his cock pointed at my face. Without thinking, I opened my mouth and took in the tip of his cock. I didn’t allow this for very long. Before Scott could cum, I turned my head away from his cock. All the while, Diane was working her magic with her mouth on my cock. She must have known when I was about to cum because she grabbed the base of my cock and squeezed hard. She continued to squeeze until urge to cum subsided.
I looked over at Scott and he was applying lube to his cock. While I am thinking he is not going to butt fuck me, Diane said to Scott. “You ready sweetie?”
Scott answered by sitting on the edge of the bed with his feet on the floor.
Diane positioned herself over him so that she could take his cock in her ass. Ever so slowly his cock disappeared into her ass. “Eat my pussy, Bill.” Diane commanded. I complied with vigor. Diane began to moan and her body jerked with multiple orgasms.
When I thought that Scott’s cock in her ass and my mouth had her totally spent she pulled my face from her pussy. “Fuck me. Bill. Fuck the fuck out of me.” “Oh fuck me” she screamed.
My cock easily slid into her soaking wet pussy. I slammed her pussy as hard as I could. I took long strokes, pulling my cock completely out and slamming it back in. Out and back in again and again as Diane screamed. Oh yes, yes, fuck me, fuck me hard, I love it, fuck, fuck me. Her body jerked again and again as she had orgasm upon orgasm.
She then surprised me by pushing me away. I stood in front of her as she lifted herself off of Scotts’ cock. He rolled away and took hold of his cock. Diane sat on the edge of the bed and took my still hard cock in her hand. “I want you to cum on my tits, so please don’t cum in my mouth.” And with that, she again took my cock in her mouth. And again, Scott watched intently. It didn’t take her long to bring me to a climax. I let my cock slip out of her mouth and shot my load onto her tits. As I backed away she took my hand held it tightly.
“OK, honey” she said at first looking at her husband then nodding toward my cum on her tits.
Scott needed no time moving to lick my cum from his wife’s tits and stomach. When he finished licking up my cum, Diane looked at my cock and nodded. Now I knew why she held onto my hand. Scott scrambled to take my cock into his mouth again. At first I thought he was just going to clean the cum and his wife’s love juice from my cock. When my cock began to harden again I thought, what the hell, maybe I could cum again. “OK. but let me lay down for this” I said.
They moved to allow me to spread eagle on the bed. Scott again took my cock in his mouth while Diane began to play with my nipples. I took one of her tits in my hand as she sucked and licked my nipples. It took a while for me to cum again but when I did Scott moaned and took then swallowed all of my cum. He held my cock in his mouth until I had completely softened.
When we stood up Diane gave me a quick peck on the lips. “That’s it sweetie, you have to go now” she said matter-of-factly.
I picked up my clothes. Scott led me to the other room as Diane remained behind with the bedroom door closed.
Scott waited patiently as I got dressed. He walked me to the door and put his hand out to be shook. The hand held two $100 bills. The best tip I ever got.
I made my way to my pick-up. Even though it was Christmas Eve, Denny’s was still open. I was hungry. I went in and ordered breakfast. My waitress tried to hit on me. She knew that I had a girlfriend. Still she flirted away. I ignored her.
