tagTransgender & CrossdressersJay's Sex Club Adventures Ch. 16

Jay's Sex Club Adventures Ch. 16


Once Holly and Jen were finished their second round that morning they got up, showered, and met me in the living room where I sat anxiously waiting to get some food in my stomach. I was surprised to see them holding hands and giggling as they came down the hallway and stopped in front of me, where I sat on the couch looking up at them curiously.

"Ready Jay," Holly asked.

"Uh... yeah."

"What's the matter," Jen questioned me.

"Are you guys... like... together?"

They both looked at each other and then back at me and proceeded to start laughing. I suddenly felt rather foolish, maybe I shouldn't have jumped so easily to conclusions.

"What happened last night was all in good fun Jay," Holly winked once they stopped laughing, and Jen had started giggling all over again, "That's not to say it won't happen again."

"But we're not a couple Jay," Jen said, "Would it be a problem if we were?"

"Of course not," I said laughing.

"As long as you get to watch, right?" Holly asked.

Once the jokes were finished, we made our way out the door and headed outside to our apartment complex' parking lot. We decided to take my car, since it had more room than Holly's and Jen had not brought her car. Before we left, we sat trying to decide where exactly we wanted to go for breakfast. After a while, we agreed on a nearby diner that Rob and I used after some of our late nights spent at the local bar.

When we got there, I was relieved at the possibility of finally getting something in my stomach. Even though my ass was aching from the fucking I'd taken from Kendra, I was bone tired all over, and still hung over from the previous night.

After we ordered our food, I couldn't take my eyes off of Holly and Jen, who sat across from me and were still flirting and petting quite heavily with one another. I believed them when they said that they weren't a couple, perhaps they were just caught up in the fun they'd had last night. Thinking about what these two girls had probably done with each other last night... it really got me turned on just to think about it.

I imagined the both of them without clothes, kissing, exploring each other's bodies, sucking each other's cocks. Then I began to wonder, who was the top? I know Jen was always more submissive, while Holly was pretty versatile. But maybe in this case, Jen would have liked to be the one delivering the fucking? I was getting carried away with my thinking, when Holly yelled my name, snapping me out of my deep train of thought.

"Earth to Jay... come in Jay, are you in there?"

"Huh? Oh, yeah, sorry about that."

"What were you just thinking about," Jen teased.

"I uh... n-nothing."

"Oh yeah? Bet I know," Holly said through an evil grin, "You must have been thinking about us last night... right?"

"Heehee... I bet he wishes he had been part of what we did last night," said Jen.

"Go on Jay," Holly said laughing, "Ask some questions."

"R-really? Y-you mean..."

I could tell by the look on both of their faces, that they were having fun with this. I found myself wondering why I was even being so shy about it really. I had slept with both of these girls countless times, separately. There was no shame in me asking them what they had done together, when I wasn't around.

"I was just thinking... if you two are going to be a couple of lesbians, at least you don't need strap-ons since you both have the real thing."

They couldn't help but laugh, and Holly reached across the table giving me a playful shove. Apparently, I had been right about Jen... while she preferred to be submissive with men in bed, she loved being dominant when it came to being with another girl like herself. And it now seemed that Holly was a switch, making her versatile by not picking one side or the other, and probably worked out really well for the both of them.

"You know," Jen said smiling at me. "Maybe the three of us could get together and have some fun as a group. Jay, I think it would be a lot of fun if you and I could spit roast our little Holly here."

The idea of Holly taking it in the ass from me, while she sucked on Jen's cock really got me thinking dirty. If we weren't out in public right now, I would probably suggest that we carry out Jen's suggestion right here, right now, at the table.

"I like that idea... when do you think we could do it?"

Holly laughed, taking a sip of the coffee she had ordered when we first got to the diner.

"I'm game," she said, setting her mug back down on the table, "really... anytime is good for me."

"I'd love to say right now too," said Jen. "But I have to go to work in a couple hours, and I'll need to head home and get ready as soon as I finish here. Um... why don't we get in touch at some point during the next week and plan something by phone, sound good?"

We were all in agreement, though I was a bit disappointed that we couldn't carry out this suggestion that had gotten me so turned on. I was definitely looking forward to the day that we actually would carry it out though.

After breakfast, we left the diner and I drove Jen back to her place before taking myself and Holly back to our apartment. I sat down on the couch and turned on the TV, flipping through the channels, while Holly made her way towards her room. She said she wanted to get some cleaning done as well as some wash, which would probably take her a few hours. As for our Saturday night, I had no clue what we were going to be up to once our sun went down.

A couple of hours passed, and Holly came out of her bedroom and sat down on the recliner across from me.

"I'm going to head out for a couple of hours to do some shopping with Annie," she said.

"Where are you two heading?"

"Probably just to the mall... might get some dinner too. I'll be home around ten. If you decide to go out, let me know so I'll have my key ready when I get back."

"No problem," I replied. "Just make sure to clear it with Rob if you decide to hook up with Annie too," I said jokingly.

"Oh, you're so dirty," she laughed.

"Ah, don't worry about it," I laughed back, "we both know Rob would happily share."

She stood up and playfully shoved me, as she always did, before leaning down to give me a kiss on the forehead. She grabbed her keys and made her way out of the apartment, leaving me behind to watch TV and try to think of something to do myself. About an hour went by, and I still had nothing planned. I stood up and was about to make my way to the fridge to grab a beer, when I heard my cell phone ringing.

I picked up the phone, the caller ID read 'Kendra'... I was a little shocked that she was calling me, and found myself wondering what exactly she might want to talk about. I grabbed the beer from the fridge before pressing the talk button, and putting the phone up to my ear.

"Hello?" I said, as I walked back towards the couch and plopped down in front of the TV again.

"Hey Jay, it's me,"

"Hey. What's up?"

"I just got done work, and I was wondering what you were up to baby? I was thinking maybe if your free, we could get together and have a little follow up to the night we spent together last night?"

I glanced over at the clock... it was going on seven o'clock, and I was still sitting at home with nothing to do but drink and watch TV all night. It sounded rather boring actually, and though my ass was still just a little sore from last night, I would have much rather spent my night with Kendra then sitting here alone and bored. Especially after all the teasing from Holly and Jen earlier that afternoon.

"I like that idea! Your place or mine?"

"Either one, doesn't matter," she replied, "I could swing by and pick you up if you want to come back to my place for the night."

Suddenly I was beginning to feel claustrophobic just sitting here alone and cooped up in this apartment.

"Sounds good to me, text me when your outside?"

"You got it babe,"

She hung up, and I stood, walking towards my bedroom to put on some fresh clothes. Before I changed, I pulled out my phone again and texted Holly to let her know I was heading out for the night.

"Hey Holly, I'm going out. Heading over to Kendra's for the night."

I set the phone down on my bed, and started my change of clothes. The phone vibrated as I was pulling on a pair of jeans, and I snatched it up again to find a sarcastically funny reply from Holly.

"Have fun, but don't complain to me about that ass of yours tomorrow."

I chuckled, sitting the phone down again and reaching into my closet to grab a new shirt. The one thing I could say was that, Kendra may always leave my ass sore in the morning, but it was almost always worth it.

My phone went off once again, but this time it was Kendra, letting me know that she was out in the parking lot waiting. So, I headed back into the living room to shut off the TV, before grabbing my keys and making my way out the door. Once outside, I got into the passenger seat of Kendra's car and glanced over to say hello. She smiled back at me.

"Hey there,"

"Mmm, can't wait to get you back to my place baby," she said.

We pulled out of the parking lot and as I sat there, I noticed that even after a few seconds, there was a very obvious bulge showing in the front of Kendra's pants. I couldn't help but laugh as I always seemed to get this girl turned on.

"Whoa... someone's happy to see me," I said, motioning towards the lump in her pants.

"Yeah... you've been on my mind all day honey. We had so much fun last night that it made it hard to finally realize I had to go to work this morning. If I could have found a way to afford it, I would have just called in sick. We would have spent the whole day in bed fucking like a couple of animals."

"I think I would have liked that," I replied, reaching over to rub her hard cock through her pants.

Kendra sighed, trying hard to stay focused on driving as I adjusted myself in the seat so that I could lean over towards her. Lining up perfectly with her crotch, I unzipped her fly, pushing her panties aside, and pulling out that perfectly massive dark cock. Already fully erect, and leaking a little pre-cum as well. I couldn't wait to taste her.

I wrapped my lips around her throbbing meat, taking every inch into my mouth and working my throat muscles around her. Kendra moaned, keeping one hand on the steering wheel, and using her other hand to tug at my hair. She was doing a pretty good job staying focused on the road, while enjoying the feel of my lips wrapped around her cock. I laughed to myself, realizing that this was a new step for me as the first time I had ever sucked cock in a car while the other person was trying to drive.

It was also funny just how much I had become Kendra's little cock sucker, as she called me. I loved being with the other girls I had met at The Raven, and I enjoyed showing many of them my submissive side as well. But it was a whole different feeling with Kendra.

It wasn't a romantic feeling or anything like that, I just really loved being sexual with her. Kendra was probably one of the best sexual partners I had, with Christy and Holly being the only other two that I considered anywhere near as much fun as Kendra.

Christy was a lot like Kendra as far as being dominant, and she knew a lot of the same moves as well. Of course, when it came to Holly there were feelings involved, but she was also great fun to be with, and we could use our Dom/sub switch capabilities back and forth as needed.

"Oh fuck baby," Kendra moaned, "Keep that up and you're definitely going to make me cum before we even get to my place."

I slowed my pace, releasing her from my mouth and sitting back up again.

"Sorry," I said smiling at her.

She laughed, tucking her cock back into her pants as we pulled up at her house and parked the car. Once out of the car, she led me into her house quickly, anxious to get me inside and have her way with me, I could tell.

She dropped her keys on the table, and turned around, shoving me onto the sofa and sitting down next to me. Quickly, she slipped out of her pants, tossing them aside and her panties soon followed, allowing her huge cock to spring totally free.

"Let's continue what you started in the car, shall we," she asked with a seductive grin.

I was happy to oblige, and after pulling my shirt off and throwing that to the floor, followed by my pants and boxers, I slid forward on the couch so that I was lying on my stomach across the cushions with my face in her lap. I took her back into my mouth, sucking hungrily, stroking and slurping. Kendra moaned as I devoured her cock, playing with her balls with one hand and using the other to reach up and rub her nipples.

"Oh baby, you sure have gotten use to my size, haven't you?"

She was right, I had definitely adjusted to Kendra's large cock, at least when it came to oral sex. Even I was impressed with how much of her dick I could take down my throat, and how easily I could do it now without choking or gagging.

"I want you to fuck me now," I said after I stopped sucking her cock.

"Someone seems awfully eager," she replied.

"Can't help it," I said, "ya got me hooked."

Kendra laughed, standing up and had me turn over onto my hands and knees, still on the couch. She planted one knee on the cushion behind me, while keeping her other foot on the floor, and angled her cock to line up with my ass. I felt her hands on my hips as she started to push into me, and I moaned, biting my lip. I was surprised to find that there was very little pain... probably because we had just done this twice last night, and my hole hadn't really had much time to tighten up again.

Kendra took advantage of the lack of pain, and immediately started slamming in and out of me, gripping me tight as she did. I moaned, panting, slumped over the arm of the couch, my ass sticking straight up in the air with her cock ramming me hard.

I guess it was mostly because of the blowjob I had given her before hand, but Kendra did not last very long. I heard her breathing becoming heavier, and felt her start to shake, her body trembling against mine. I felt her cock beginning to swell up inside of me, and she bit my neck playfully as she slammed herself all the way into me and let loose.

"Oh yeah! Fuck Jay, your ass feels so great," she cried out, as her cock spewed her cum deep inside of me.

She was shaking, and I could feel her pumping me full of her load, before she slipped out of me and lay back on the couch. I sunk into the cushions sighing, as I felt her semen leaking out of my ass and down the back of my leg. I sat up, turned around and decided I wasn't done yet... I didn't mind that she had gotten off so quickly. But it was not going to end that soon.

I reached out and took hold of her still semi-erect cock, and started stroking.

"Mm... you want more," she whispered.

"Definitely," I replied, my hand gliding up and down the length of her cock.

I took pride in how fast I managed to bring her back to full erection, and I found myself taking control of the situation now.

Once she was hard enough again, I got on top of her, lining my ass up with her cock and lowering myself down onto it, feeling every inch slipping into me again. I moaned, easing my way down onto her, I knew I had to be easy on myself. Even if I was use to it now, with a girl as big as Kendra, I could hurt myself if I wasn't careful. Once I had lowered myself down onto her completely, Kendra took hold of my hips, and I started riding her. I ground myself against her throbbing cock, humping her, moving slowly up and down, taking it easy at first. Then, after about a minute, I started moving up and down faster and coming down onto her harder, flesh slapping against flesh.

We kept it up just like that for about three minutes, before Kendra slid out from underneath of me, her cock sliding out of my ass, and she took my hand and pulled me off the couch.

"Let's go to my room baby, much more comfortable there."

I followed her down the hallway and into her bedroom, lying down onto my back, on her comfortable mattress. Kendra climbed onto the bed with me, moving on top of me and leaning down to kiss me on the lips. I parted my legs, as her tongue slid into my mouth, and I felt her lifting them up and her cock pressing against my hole again. She shoved herself back into me, and I let out a low grunt as I felt her thrusting deep inside.

I could lay there on my back, with her thrusting hard and deep into my ass. We were in just the right position to look each other in the eyes or make out while she fucked me. I felt my ass clamp down around her cock, as my own orgasm took control and I cried out in pleasure. I felt her swelling up yet again, and she kissed me passionately, our tongues dueling as her cock erupted once more.

She pulled out after a few seconds, as we tried to catch our breath, and lay down at my side. My ass was definitely starting to get sore now, and I wanted to go again but I knew my limits. So we just laid there, in silence for a few minutes before Kendra finally spoke, breaking the lingering silence.

"You really seem to be getting into it more, baby,"

"Yeah," I replied, "I have to admit, in the beginning, I was really nervous about being with someone as big as you. But' I've gotten use to it, if anything, I really enjoy it now."

She laughed, turning over onto her side and kissing me on the lips. "You know Jay; I really like what we got going between the two of us. I have so much fun with you when we get together."

"I feel the same, especially the last two nights," I replied honestly.

"So, can I ask you a question?"

"Uh... sure, what's up?"

She seemed to be hesitating, running her hands through my hair as we laid there in silence once again and I wondered anxiously what exactly she wanted to ask me about.

"Would you want to actually go out with me?"

Wow, that was definitely dropping a bombshell on me. I had never expected Kendra to ask me to start a relationship with her. Honestly, I didn't know how I really felt about it either. What would be the right answer... I didn't want to hurt her. Hell, I almost worried she might try to break me in half if I told her no. At the same time, I didn't know if I was NOT interested.

"It's okay to say no, you know," she said interrupting my thoughts. She must have sensed it through my hesitance to answer the question.

"If you're not interested, I won't be heartbroken baby. I just thought we had good chemistry."

"I think we do too," I answered, "But... I don't know. I don't know if I'm looking for a relationship right now. I kind of like things the way they are between us right now."

"That's okay honey," she laughed.

I could tell by the tone of her voice she was being sincere, she didn't sound hurt, nor did she sound like she was trying to hide her 'pain'. And I was normally pretty good at reading people when they did stuff like that, so I could tell."So... we're cool, right," I asked, just to be sure.

"Baby, we are as cool as ice,"

I laughed, and so did she. We lay there a little while longer, talking and joking and flirting with each other, before we fell asleep like that. I woke Sunday morning, still in her bed, wrapped in her arms, the warmth of her body making me feel a little too hot. I shifted slightly, and felt something hard poking at my thigh, she obviously had a pretty big case of morning wood. I shifted some more, slipping out of her arms careful not to wake her and slid down under the sheets until I was within eye level with her hard-on.

My own cock becoming hard, I leaned closer and accepted her into my mouth, tasting the remnants of her cum on her as I took her deep into my throat and started to suck. She groaned, waking slowly to the feel of my lips around her as I licked and sucked. I moved from her cock, down to her balls, sucking on each of them one at a time, and then sliding my tongue back up the length of her shaft to swallow her whole once again.

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byWhiskeyIsGood© 14 comments/ 32053 views/ 32 favorites

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