Rachel and Chris

She answered by squeezing my cock, which she had stopped massaging as her climax was building. Then she lifted her chin up and kissed me while gazing into my eyes.
“What a sexy and incredible girl,” I kept thinking to myself as I took a napkin and discreetly placed it under the table and into her hand rubbing my cock. She took the hint and used it to clean up much of the semen that was coating me and her small hand.
“How about we continue this back at my place,” I asked.
I didn’t know what to think for a moment because Rachel didn’t respond but seemed lost in thought. I began to think that she was all about “heavy petting” as they use to call it but didn’t go any farther. I was hoping such wasn’t the case but was resigned the possibility. I thought that either way she was great.

“Jack, let’s go,” she said very carefully and thoughtfully as she squeezed my hand. “But let’s go back to my apartment if you don’t mind.”
I didn’t mind. If it was fine with her it was fine with me. Her brother being there was a bit weird for her I thought but it didn’t bother me in the slightest. I assumed that with her dating he had likely seen many of her boyfriends come home with her.
Before I could reply and react, Rachel added: “Don’t worry about my brother. I don’t think he will mind.”
Thinking he wouldn’t mind was not exactly reassuring but it was more a problem for her than for me so off we went.
As we drove back across town to her apartment, Rachel began to tell me about her brother as it seemed she wanted me to be fully briefed before we made it to her place.
“I love Chris with all my heart and I will not let anyone hurt him,” she said as I wondered what this was building toward.

“My mom and dad couldn’t go a day without putting him down and treating him like crap. It didn’t matter what he did, he was wrong. His friends were bad, his effort at school was bad, the way he dressed was bad, and on and on,” she said.
“Chris has been different since we were little kids. He always wanted to play with my toys and dolls; wanted to play with my friends and not the other boys, and; got caught over and over dressing up in my clothes.”
“When I was in middle school and started wearing more grown up things, my Dad caught him dressed up as a girl one afternoon and just lost it. He didn’t hit Chris but he called him so many things that Chris wouldn’t even speak for several weeks afterward,” she continued. “They sent him to all kinds of counselors but the fact was very clear that he wanted to be a girl.”
“When he was sixteen, and had been to over a dozen counselors, one of them told my Mom and Dad that he was “trans-gendered” and we all had to learn about that. All the while, the only person Chris would talk with was me and even then he was limited in what he would share,” said Rachel.

As she was telling me this I was wondering how she would take it if she knew that I had been with a couple of TG girls before. I wasn’t about to tell her that it was one of my great fantasies.
Rachel continued, “It was impossible for me to understand how my parents, who were very loving to me and our younger siblings, could be so rejecting and hateful toward Chris. It wasn’t as if he decided to be a girl for sex or something. He was doing it as a little kid and they tried to ignore it but couldn’t.”

By this time, Rachel had my hand between in hers on her lap right on top of her hot pussy and was showing plenty of leg. She was so hot and I was looking forward to having her petite body on top of me, with her long hair and breasts hanging toward my mouth, while she fucked my cock with her hot pussy. There’s little like the look of a hot woman when she reaches orgasm while on top of your cock.
“Chris was not out screwing around in high school, in fact, I think he is still a virgin in every sense of the word,” explained Rachel.
“But, as soon as I started college I knew that I had to get him out of the house so he wouldn’t be put down every day and feel so depressed. And, since we got the apartment two year’s ago, he has quit being down and seems happy. He has some good friends from school, girls and guys, and seems to be getting along with everyone although I don’t think that he as actually let all of them know of his leanings,” she said.

Laughing now, Rachel said: “The only bad thing about having Chris in the house is that he keeps borrowing my underwear!”
“I just wanted you to know, because at home Chris often dresses as a girl but so far I’ve never seen him do so outside of the house,” she added.
Understanding now what her hesitation was about going back to her place, I asked some questions to let her know that I wasn’t shocked in any negative way.
“Do you help him put on makeup and everything? Do you fix up his hair? Does he look like a girl?” I asked Rachel.
“Yes,” she said. “I’ve taught him how to wear his clothes and do his makeup and hair. And, yes, he does look very pretty when he is dressed as a girl. I’ve told him that he should go out because no one would even think he wasn’t a girl. But, so far he has been satisfied to live in the apartment as a girl without letting others know,” she told me.

“Does he want a sex change?” I asked as I shifted gears exiting the freeway and then put my hand back on her lap.
“I asked him that and he said that he doesn’t think so,” she replied.
“I do know one thing, and don’t you tell him I told you!” she said laughing.
“What?” I said as I looked at her sexy lips.
“He seems to like having a dick! I’ve caught him masturbating many times when we were younger at home and now that he has his own room, I know that’s what he is doing in there sometimes,” she explained.
“And I know something else about him that he doesn’t think I know,” Rachel declared as if telling me a state secret. “He has a vibrator and uses it on himself because I can hear it buzzing through the door!”
“So he likes the best of both worlds?” I inquired with a raise of the eyebrow in her direction.

This comment seemed to make her think for a moment as we drove closer to her apartment. I assume that she thought I’d say nothing, object, or just be polite about it. Instead I said something that suggested some understanding and curiosity. I don’t think she was expecting that.
I pulled up before the apartment and before we got out of the car we exchanged a very hot, wet, tongue-tied kiss. My hand went back to her pussy and gave it some attention as we kissed. She had her hands on my cock almost immediately and it was as hard as possible once again.

As I moved my kisses to her ear, I whispered to her that it would be exciting if she would give me a blow job while we were sitting in the car out front. No objection was forthcoming but my cock was. It was pulled right up and out by Rachel as she lowered her sexy little head down and took my slick dick into her hot mouth.
Her tongue swirled around the head of my cock and she gripped the shaft firmly with her head. I was lifting my hips up to get more in her mouth while beginning to tickle her asshole through her panties as she was bent over the console sucking me.

She moaned each time I applied press against her sphincter so I thought that to be a sign that she may have a fun-loving ass which is always a plus. She sure knew how to work her mouth around the most sensitive parts of my cock and I was about to blow.
“Rachel, I’m going to come baby!” I declared in time for her to pull off if she so desired.
She stroked my shaft and took my come on her lips and around her mouth. Not exactly swallowing but not turning away either, she rubbed the come around on her lips with her tongue and scooped much of it up with her hand. Grabbing a napkin from the map pocket right in front of her on the door, she cleaned me up and wiped her face off while looking at me with the best “fuck me” look I’ve seen.

Part 2
In the Apartment

We managed to gather ourselves and get out of the car. We laughed and touched each other as we stumbled to the door. Just as Rachel opened it, she put her finger to her lips for me to be quiet.
As we walked into the entry, which was a short hallway, Rachel loudly called “Chris, oh Chris.” And as he likely thought her to be alone, he walked into view by the sofa which we could see plainly.
Maybe I should rephrase. She walked into view.
Rachel was right on all counts. Chris was as hot as his year older sister but with shorter hair in a pageboy style cut. Chris was dressed in mid-thigh length skirt, bare feet, and a white blouse. Her legs were every bit as smooth and attractive as his sister though slightly bigger but still petite when compared to most guys.
As Chris noticed me he seemed to be shocked that Rachel would have brought someone in the house without telling him. And, as Chris stood looking, not knowing what to say or do, his big sister Rachel, the girl who had been well mannered the whole time, spoke loudly to him.
“Don’t worry Chris, this is Jack. I just sucked his cock and he is about to fuck me!” she said in a very tipsy voice which clearly indicated that she was more intoxicated from the dinner than I thought. I guess talking about the serious issues of her family had masked her state of mind.

Now I was a bit shocked and looked at Chris with an equal expression of shock. That statement did not sound like the Rachel I’d been with all night.
Next thing, again before Chris or I could say or do anything, Rachel reached back and unclasp her little back dress and let it fall to the floor.
Here I was. Staring at this gorgeous twenty one year old Latina with long dark hair a perfect bronze body standing in heals and encased in sexy black lace-front panties and a matching mid-length bustier which was what she was using to push those lovely tits up so high and firm.
Chris, her brother looking much like her sister, was on the other side of the room and appeared to be shocked by seeing her this way as well. It certainly appeared that this was not normal behavior between them. And, all of this theater from lovely Rachel had so distracted Chris that he wasn’t any longer thinking about his appearance.
“Wow sis,” he finally said breaking the silence, “you sure look hot!”

Chris’ voice was just a bit lower than what you’d expect from a girl his size but not manly in any way. He laughed as he told his sister that she looked hot.
It was at that moment that a wave of embarrassment passed over sexy Rachel who stood there in black lace and high heels between her boy-girl brother and me, her date and a man twenty years older. I stepped in to squeeze her against me and she wrapped her arms around me and began to giggle.
“Which way to your room?” I asked.
“This way,” she said as she tugged me off and through a door which she closed as we fell through arm in arm.
Leaving Chris in the other room without another thought at the moment, she turned her petite, sexy body toward me and began kissing me as she unbuttoned my shirt and pulled it off. Next she undid my slacks and let them fall to the floor as she pulled my boxers down after them.
Kneeling in front of me, Rachel again took my now very stiff cock in her mouth and began to suck and lick as she fondled my free handing balls. I ran my fingers through her hair on the top of her sexy head as she sucked me and squeezed my ass and balls with her hands.

“Oh Rachel that’s good,” I said as she took me to the back of her throat clearly having learned to deep throat as a good young upper middle class american girl.
Even better, taking a hint from my previous actions with her in the car, she took a finger to my ass and began rubbing my semen and her saliva all over my asshole applying pressure as she deep throated my cock.
Here I was, an old man when compared to her, and I was about to come a second time in less than twenty minutes! What a sexy, talented lover Rachel had turned out to be. She may have been used to young college boys having this type of recovery and stamina but if she knew what a deal it was for me she would have been proud.
Still wearing her sexy bustier and black panties with her heels on, she was so gorgeous to view as I looked down and saw her silky dark hair spread across her back. Then she did it: She pressed her finger slightly into my asshole, applied pressure to my cock with her mouth and tongue, and looked up at me with those big dark eyes. My sphincter clamped down on her finger as my cock began shooting come.
Rachel kept taking my much smaller load of come in her mouth and massaged it all from my cock using her tongue and lips and free hand. She pulled her finger from my ass and then stood up suddenly and pranced off to the bathroom.