My name is Samantha, my best friend, Greg, and I were driving across the country heading to my new school, my new life in fact.

Greg and I have a special relationship. We have known each other since we were kids, we have never fought, and most importantly, he knows I am a trans girl.

It hasn’t always been easy for us, and it has been a bumpy road sometimes, but he always ends up giving me his full support.

Now we are friends, but also friends with benefits. We are both bisexual, and we have had oral sex with each other numerous times. He has even fucked me, but I had never fucked him.

It was the end of August, and it was hot and muggy; I was wearing a tank top and a short skirt; my bare feet were perched on the dashboard. Greg had his shirt off and was wearing his board shorts. I glanced over as the sweat glistened on his muscular chest and biceps. I had to admit, he looked quite sexy.

The conversation turned to sex, as it often did, and Greg mentioned a few things from his sexual bucket list. “Group sex” and “Blowjob, while driving,” were at the top of the list. I smiled and decided to take care of one right away. I leaned over and took his already hard cock in my mouth; The musky taste of his cock; the speed of the car, added to the danger; Added to the turn-on. I licked the sides of his cock, and then I took him deep in my mouth and moved up and down the length of his cock, trying not to bang my head on the steering wheel. Greg started to squirm in his seat as he began to cum in my mouth. He came a lot, and I tried to contain it all.

“Fuck,” he said suddenly.

I looked up at him quizzically.

“There is a woman in the next car watching us,” he told me.

I instinctively lifted my head and looked out the window. There was a woman in the passenger seat of a car watching us and was very excited to see my head pop up from Greg’s lap. She turned to the man in the driver’s seat, excitedly as if she won a bet. The woman smiled and gave us a thumbs up, as they sped away. I swallowed the rest of Greg’s cum, and then we started to laugh hysterically.

“Blowjob while driving.” Check!

“Sex in public.” Check!

We checked into a motel for the night. It was still sweltering, so we decided to go to the pool for a burger and a swim. There were two other couples there, a middle-aged couple about fortyish and a much older couple about sixty.

Greg was swimming laps as I climbed out of the pool and was drying off as the older couple was leaving.

“That’s a man,” The older man whispered to his wife about me.

The older woman looked at me and the bulge in my bikini bottoms.

“You're right, there outta be a law,” the older woman answered.

I was speechless as this stung me deeply. I turned away as if I didn’t hear the couple. Then I heard a woman’s voice.

“If there were a law against being an asshole, you would get life,” The other middle-aged woman said.

“What did you say?” The older woman said, shocked.

“What are you deaf, narrow-minded, and stupid?” The younger woman answered smartly back.

The older woman looked to her husband.

“Are you going to do anything about that, Jim?” The older woman said to her husband.

“No,” He said matter-of-factly, and then walked away to their room.

The older woman paused for a moment and then followed him.

“Thank you,’ I said to the woman.

“No problem, it made me feel better, and she was a judgmental bitch,” The woman said.

“Well, it was very nice of you. I’m Samantha,” I said, extending my hand.

“Carole,” she said, shaking my hand, “and this is my husband, Alan,’ pointing to the man at the table.

Greg climbed out of the pool.

“This is Greg,” I introduced.

“Boyfriend?” Carole asked.

“No, just friend,” I told her.

“Very special friend,” Carole said slyly.

That is when Greg and I both realized that this was the woman from the car that was watching me give Greg a blowjob.

That could have been an awkward moment, but instead, it broke the ice, and they invited us to join them and have some wine.

Carole and Alan were married for twenty years and had two grown children, and they were just finishing their vacation. Carole was blond, tanned, and pretty, and she had large breasts and full-figured and very sexy. Alan was balding and had a paunch and was extremely funny, but also very good-looking. Greg and I told them our story, and they seemed genuinely interested, and I think a little turned on.

The wine was flowing, and Carole admitted that they enjoyed swinging and steered the conversation to sex, while also trying to steer us to their motel room.

I whispered to Greg and asked what he thought, and he said this could a once in a lifetime event.

I nodded, and we agreed to join them in their room. Alan poured us some more wine, and Carole wasted no time and started to kiss me. She told me how beautiful I was, which made me blush. Carole gracefully untied my bikini top and admired my small breasts. She sucked on both nipples, making them hard and sensitive. Carole then went to her knees and, in one motion, pulled off my bathing suit bottoms. My shaved cock bounced in front of her smiling face.

“What a beautiful clit,” she told me.

Carole then took me deep into her mouth. She massaged my cock with her tongue and her lips as she deep-throated me. I looked over at Alan and Greg on the other bed, and they were already naked, and Alan was moving to suck on Greg’s cock.

Carole pulled her sundress over her head to reveal her incredible naked body. Her large breasts and hard brown nipples begged me to suck on them. Carole moaned as I took each nipple in my mouth and sucked.

Carole then took me to the other bed and positioned us into a sixty-nine with me on the bottom. Carole had a well-trimmed pussy, with a large, brown labia and a huge clit. She moaned loudly as I tongued her.

I looked up just as Alan was guiding Greg’s cock into Carole’s pussy. I had a fantastic view of Greg’s cock sliding into Carole’s pussy. I rubbed Carole’s clit as he fucked her hard. It wasn’t long before Carole was cumming hard.

“Fuck me hard, Greg, fill me with your hot cum!” Carole screamed.

“Fuck that pussy hard,” Alan encouraged.

Greg started to pound her faster until he came inside her. I loved the close-up view of Greg’s cock and balls pulsing as he came. When Greg pulled out, his cum dripped from her pussy, and I greedily lapped it up. My licking caused Carole to cum again.

We all spread out on the bed and took a break with some wine and brief conversation. Carole was playing with Alan’s hard cock as Alan looked at me lustfully.

“Alan, would you like to fuck my pussy?” I asked Alan as I ran my finger around my tight asshole.

“God, yes!” Alan said quickly.

I laid back on the bed and spread my legs. Alan lifted my ass and started to tongue my asshole, lubing me up. I looked over at my audience of Greg and Carole, and they were masturbating each other as they watched the show. Then Alan positioned his cock on the opening of my tight pink hole and pushed his cock into my boypussy. Alan’s cock was about the same size as me, but a bit larger cock head. I craned my neck to watch him push his cock into my asshole. He completely filled me up and didn’t waste time and fucked me hard. Alan grabbed my ankles and thrust his cock into my tight hole. Alan started to fuck me hard and fast! Carole came forward and began sucking on my cock. This was so intense, watching this husband and wife sucking and fucking me. I started to cum right away in Carole’s mouth. Alan asked to cum inside me, and I begged him to cum. Alan quickly shot his cum deep inside me; it was incredible. Alan kissed his wife’s cum lips, and we all fell into a heap on the bed.

Greg fucked Carole one more time, while I gave Alan a blowjob as he watched his wife being fucked by the younger man. They all came within a minute of each other.

Afterward, we exchanged emails, and then we went back to our room.

The next morning, we happened to meet them at breakfast.  It could have been awkward, but it was enjoyable. We told them about our group sex bucket list, and they laughed as they told us they checked off quite a few boxes as well.

Greg and I drove off, smiling.