Cheerleaders of a Certain Age

My high school reunion was coming up. Two decades had passed, and I still had fantasies about the girls I knew back then.

I was a scrawny dork in school, and dating the hot girls was out of the question. I doubt any of them remembered me.

News of the reunion was on a social media site where we could add information and send messages. I updated my information, and to my surprise one of the old cheerleaders, Gail, sent me a message about something I had written.

We started exchanging messages. She had married her high school boyfriend, a football player, but said that the marriage didn't last long. She divorced him and remarried.

By now I had blossomed into a normal looking guy, much improved over my teen years.

Gail and I bantered back and forth for a few days online. Even though years had passed, she was just as appealing.

I decided to take a leap. In response to her message about her first marriage to the hunky football player, I wrote, "Going back to your first marriage, what went wrong? Dick too small?" I hoped she would understand that I was making a joke.

She didn't respond for a while, and I feared that she took offense. So I added, "Only kidding."

A day later she replied, "How did you know?"

I wrote her, "Oh, ha, I was just thinking about the old joke about the handsome athletic guy who has everything, except...."

She sent a happy face emoji.

Even though I ad been a loser in the looks department back in school, my cock size was a winner. Over the years news of my cock size has opened up many opportunities to fuck married women, many times as a bull at the invitation of husbands.

Her next message popped up, "Ha! We were young."

I replied, "Too bad you weren't dating me back then."

She wrote, "Oh?"

"Dorky as I was, I didn't have your first husband's problem."

Gail replied, "Oh?"

I wrote, "I'm blushing."

She wrote, "LOL, Size isn't everything, but you sound like a boy I'd like to meet."

"You will. At the reunion," I typed. Then I added, "Can you still fit into your cheerleader outfit?"

She wrote, "Sort of." Then she told me that she and another former cheerleader were thinking about putting on their old uniforms to lead a cheer at the reunion.

"I look forward to that," I told her.

She didn't respond, and I thought it was best not to try to keep messaging unless she initiated something. So we fell silent.

A month later, I checked into the hotel for the reunion. At the opening reception that evening I saw Gail with her husband at a table with other former in-crowd alums.

I walked over and smiled. Gail looked up, "Greg, is that you?"

I said, "Hi! It's been a long time." I shook hands with her husband, then leaned over to give Gail a friendly hug. Nearby Millie, her other cheerleader friend, watched and then exclaimed, "You don't look like your old self. Some things do improve with age."

Gail's husband asked me if I was playing in the golf tournament the next day. "No, not me," I replied. "I may have better things to do," I winked at Gail then asked, "What are you doing tomorrow afternoon?"

She smiled, "I'm not sure. Probably hang out with Millie."

I nodded then spoke quietly to her, "When your husband is golfing, why not come to my room? Number 922," and then walked away.

At the breakfast buffet the next morning, I waved at Gail and her husband as I passed by their table. "What time is the golf outing," I asked.

Her husband said, "Ten o'clock."

"Good luck," I told him, and I winked at Gail. "I hope you'll have a good day, too." I had a second cup of coffee then returned to my room to wait. I put on stretch nylon briefs that I wear for husband-wife bull sessions. It allows lots of room for cock expansion.

Eventually, there was a tap on my door. There was Gail, dressed in a hotel robe covering her beachwear.

"Come in," I welcomed.

"Well, okay, but I'm on my way to meet Millie by the pool."

"She can wait for you, I'm sure," I said.

Gail did not say anything as I motioned for her to enter. She looked at the view from my window and didn't speak. So I asked, "Are you here to satisfy your curiosity?"

She looked down between my legs.

"Watch it grow," I said.

Her eyes were glued on the inflating cock holder. My balls and cock filled it when not aroused, and now Gail could watch the shapes change as my dick looked for room to grow.

"You want to see it, don't you?" I asked.

I was pushing her to make a decision. Her better judgement probably told her to be careful, but I hoped this was an offer she couldn't refuse.

"Whew, you're having quite an effect on me," I said as my cock squirmed and pressed hard against its inadequate restraint. "If you'd prefer to go, that's okay," I added, wanting to put her at ease.

Before she could speak, I went ahead and pulled aside part of my pouch, revealing an inch or two of thick stem bending into view. I pulled the other side, and both balls dropped out.

"You don't have to speak," I said. "Just know that you can leave any time you want." Then I pulled my briefs down slowly to give her time to leave if she felt nervous.

My cock was being exposed as I had done it so many times before as a bull for a wife. I stopped when five inches were in view. "Do you want to see the rest?" I asked. "You should see it all so you can tell Millie about it."

She smiled as I dragged down my briefs until the ridge of my bellhead caught the fabric. All eight inches were in view, minus my dick crown. With a little care, I released my full cock. With the added cock head now in view, Gail saw my fill size wave up and down.

I thought back to the time when a wife wanted to back out when she saw my full size. She exclaimed, "I'm afraid to try it!" I didn't mind. It was a compliment nonetheless. Her husband talked her into sucking on me and watching her give me a hand job. He was clearly excited to watch his wife with my cock. After licking my cockhead and trying it in her mouth, she changed her mind. It was a tight fit, but we took our time getting my big bull cock into her pussy.

Would Gail back off?

"There's no charge to touch it," I told her.

As Gail moved toward me, her robe parted more to let me see her little bathing suit barely covering her pussy. She reached out and grabbed me.

"You're free to go, you know," I said. "But as you can see, I am ready to provide you with any service you may desire."

She hefted my cock and wanked me, then reached down to gather my balls in her other hand.

"This was all here in high school," I told her. "But sadly no one seemed interested back then."

Gail looked up at me and said, "I'm interested."

I didn't need more of an invitation. "Go over to the sofa and lean over," I told her.

She stepped across the room and bent over the arm of the sofa. I approached her from behind and lifted her robe, revealing her round ass covered only by her bathing suit bottom. My cock waved back and forth, slapping up against Gail's open legs.

"It's easier if we start this way," I said, as I rolled her suit down. Her ass globes were full. I looked at her crack splitting her cheeks and falling down out of sight. I stood center-ass and gripped her cheeks in my hands, pulling them apart.

"Bend down more," I ordered. "Spread."

No hands were required to direct my cock. I stepped forward to let it kiss her pussy entrance. Gail shuddered and tried to look back. "Eyes straight ahead," I told her. "Try to relax."

Those were my last words before entering her from behind. She felt herself being spread wide by my thickness, and I gave her time to assess the sensation. "This position helps you take a bigger cock," I said. "How's it going?"

Gail exhaled and answered, "I still can't believe that thing is real." In response, I pushed into her another few inches then began the rhythm of full penetration. A little push in, then out, then in and pressing briefly, then out. Back and forth in predictable motions so our bodies knew what to expect as I went deeper into her pussy.

Once fully inserted, I began a slow fucking. Gail tried to reach back to feel my cock in her pussy, but I grabbed her arms and pulled them back so she was helpless as I fucked her.

I exited her and laid on the floor, "Why don't you control things for a while?" I asked.

Gail flipped off her robe and tore away her suit top. Her tits flopped out, the same ones I desired in high school. She stepped over me and squatted down on my dick. My view of her pussy was divine. I had beat my meat many times while imagining this same pussy. We locked fingers and held hands as she rocked up and down. At that point, I heard her gasp, making involuntary sounds of womanly pleasure.

Her knees tired, so we uncoupled. We stood, and I drew her near me. We kissed, finally, and I said, "Seems kind of late to finally kiss." She laughed as her hand found my dick. I lifted her up so she could wrap her legs around me, and I guided my cock into her pussy as she slid down on it.

It was easy to hold her and kiss while my cock diddled her. I asked, "Is Milly still waiting for you by the pool?"

Gail was startled, "Oh yes!"

"Why don't you call her and invite her up to my room?"

I handed Gail her phone. While she was impaled on my cock, Gail rang her friend. "Sorry I didn't get to you, Millie. I'm with Greg in his room. Why don't you come up?"

I unlocked the door and then took Gail to the bed, held her legs wide apart, and entered her pussy for a proper fucking. With careful cocksmanship I got her to the edge again as I heard a knock on the door.

I called out, "It's open, come in."