Amanda and Me Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

We climbed in, buckled our seatbelts and Amanda quickly navigated the industrial park and got us back on the freeway. Chatting as we made our way back to the city the conversation started out light and then slowly turned to sex and sexuality. I tried not to be too curious but Amanda was an open book and she explained how when she was growing up she always felt different and that by age ten her mother had found her trying on women's clothes. Amanda was grateful that rather than scolding her her mother had helped her to figure out who she really was.

"How about you cutie? Did you always like cock before you met me?"

"Ummm, not really. I always considered myself straight but the last few years I really got into watching shemale porn. There is just something so amazing about a sexy, feminine girl with a cock between her legs."

"Yeah, when I pulled my panties down Friday night I could tell it wasn't the first time you had seen a girl like me. The lust in your eyes would have been obvious to a blind man. I just didn't know if you were one of those insecure guys who needs to be on top so you don't feel gay or something."

"No, I don't feel gay being with you. In fact, letting you be on top and dictate the action has been a huge turnon for me. Even though this is my first real experience with anything like this it just feels natural to be that way with you."

"Good, I'm glad to hear that because I've always been very sexually aggressive. I love to take charge and try new exciting things like we did back at the warehouse. That was actually the first time I've ever been blown in public before. It was also the first time I have ever given a facial before. Sorry about not warning you first."

"No problem, it was definitely a surprise but I'm really glad you did it. Like I said, this is all new experiences for me but I'm pretty much willing to do anything you want to try sexually... Well, within reason."

"You really are amazing." With a contented sigh she glanced down at her skit and said, "Now look what you've done, just thinking about it is starting to make me hard again."

Never the shy one Amanda took my hand and placed it on her skirt so I could rub the bulge underneath. After a few minutes of rubbing she hiked her skirt up again so I could rub her cock without any material in between. Her cock wasn't as hard as back at the warehouse but as I pumped the shaft it got harder.

"Want another taste?" she teased with a wink.

I was a little unsure what she meant at first but when she looked down at her cock and then back at me I smiled and undid my seatbelt. Leaning over into the driver's seat I tried to avoid the stearing wheel as I put my head in her lap and took the head of her cock in my mouth. Once again I tasted a trickle of precum from the tip which only got me more turned on. I began licking the side of her cock while at the same time using my right hand to play with her balls.

At first the motion of the car and the thought that someone could possibly look in and see me made me a little timid. But Amanda's soft moaning and my realization that the windows were tinted relaxed me and I focused all my energy on making her happy. I went down on her cock as far as I could before I had to come back up for air. Repeating the process a few times I was startled by a car honking close by.

Amanda glanced over at the car that honked. "I don't think that was for you but if it was they must have been jealous. You have a very talented mouth, are you sure you haven't done this before?"

Blushing, I returned to bobbing my head up and down on her cock for a few minutes until I felt the car exit the freeway. Lifting my head up I continued to stroke her cock with my left hand as I directed her to the visitor's parking lot at my apartment complex. After parking I reluctantly let go so Amanda could slide her skit back down and we could head inside.

Bursting through the door into my apartment we were all over eachother. Our mouths met while our hands snatched at clothing. Her tank top landed by the door, my shirt by the couch, her skirt by the bathroom and my pants and underwear just outside the door to my bedroom. Turning to head for my bed Amanda stopped me by hugging me from behind. Whispering in my ear, "Stay right there baby", she left a trail of kisses down my back. Reaching my butt she planted a kiss squarely on each cheek.

Using both hands she spread open my cheeks and licked a path from the top of my butt, down my crack to my hole. It felt so good that I thought my knees were going to buckle so I had lean forward and support myself with my hands on the edge of the bed as Amanda stuck her tongue deep into my clean ass. I could feel the swirl of her darting tongue on my hole as my rock hard cock bounced between my legs.

Reaching around Amanda took my cock in her hand as she buried her tongue in my ass. Using her fingers she tickled the underside of my cockhead as she ran her thumb along the shaft. Slowly tightening her grip she began stroking the length of my shaft as her warm, wet tongue continued probing my hole.

In a daze I felt her hand leave my cock and I heard the sound of lotion being squirted. I looked back just as Amanda stood up behind me with her eight inch cock glistening in her hand. She grabbed my waist with one hand and guided herself with the other, quickly positioning her cock at the entrance to my pre-lubed hole. Applying pressure she was able to pop the head of her cock into my ass without nearly as much trouble as Friday night.

"Oh yeah, that feels amazing. I can't believe you're still this tight after we did it on Friday." Slowly pushing more of her cock in my ass she moaned and added, "Oh baby, I could do this every night."

As my ass stretched to take more of her large cock I let out several moans of my own. Although there was still some pain like there had been on Friday night it subsided and turned to pleasure much faster. Once again Amanda took her time and slid her cock in inch by inch until she got the entire length in my ass. Waiting a few seconds for me to completely relax she began to slowly slide it back out.

Amanda had her hands on my hips as she gently started her in and out motion. Picking up the pace she penetrated me with long strokes that went so deep that I could feel her balls brush against mine. As she continued to increase her pace she tightened her grip on my hips as she leveraged her thrusts deeper into my willing ass.

I reached back and played with my still hard cock, making sure to keep my stroking at a light pace so as not to hasten my orgasm. Finally getting the strength back in my legs I straightened my upper body so she was now fucking me while we were both in the standing position. I turned my head to look back at her and our lips and tongues met as she continued thrusting. I had no idea that being penetrated while standing would feel different than it did being bent over but somehow it did.

After making love to my ass for a few minutes Amanda slowed to a stop and then withdrew her cock. "Want to lay back on the bed?"

"Sure", I said as I walked over and laid down on my back. She climbed up on the bed with me and spread my thighs as she glided her still wet cock back into my tight ass. Grabbing each ankle she spread my legs even wider to get better access to my hole. Looking up at her beautiful face we made eye contact and smiled at eachother as I reached down to resume stroking my cock. Her small perky breats bounced in rhythm as she penetrated me and her smooth body glistened as she worked up a sweat. I looked down past my own cock and watched her cock disappear into my ass and then quickly reappear as she pulled it back out.

Watching the penetrating motion of her cock in my ass was a huge turnon. I had watched it online but nothing compared to the experience of watching it and feeling it actually happen. I started thinking about the fact that in the past when I watched straight porn I always masterbated by imagining that the cock was mine but that it was the opposite when I watched shemale porn. Even when it was just a solo shemale I always imagined myself pleasing her and fantasized about her shooting her cum on me. I was brought back to reality by the thought that fantasies do come true.

Amanda brought both my legs down to one side and continued fucking me as I lay on my side. Gripping my upper hip with both hands she was able to leverage her cock even deeper into my ass. Leaning my head back and closing my eyes I focused on the sensation of her full penetration. It felt unbelievable, like every pleasure giving nerve ending in my ass was being stimulated for the very first time in my life. Her large cock seemed to fill me completely and give me more pleasure than I thought possible.

Opening my eyes and looking back up at Amanda she winked and gave my butt cheek a light pinch. We were both breathing heavily as I wiggled my ass in reponse and Amanda started to hunch over a little as her thrusting went deeper and deeper. Putting more of her weight on my hip caused my legs to start to straighten out a little. Continuing the movement I slowly straightened them as I moved into a position where I was laying face down on the bed with Amanda laying on top of me with her cock still pounding my ass.

By then the speed of her penetrating thrusts and her corresponding moans had increased to a frantic pace. Laying on top of me she continued to furiously pound my ass before finally slamming her cock in as far as it would go. She gave a girlie little scream at the same time that I felt her cock unload a flood of cum deep into my bowels and I could literally feel every part of her cock convulsing as her hot cum filled my ass. Her feminine grunts continued as I felt her body and breasts press firmly against my back. Placing her hands over the top of mine I felt her orgasm subside and her body finally relax as she lay breathing heavily into the back of neck.

"That... was... awesome!", she managed to breathe out as she caught her breath. "It takes a special guy... to give me two great orgasms... in one night."

I smiled into the pillow as I felt her slowly lift her upper body up off of me. Her lower body followed and she slid her now mostly hard cock out of my ass. Slowly lifting myself up from my face down position I practically had to peel my body from the bed, especially my rock hard cock. Sitting up on my knees I looked down at my throbbing cock and then over at Amanda when I heard a small sound of surprise from her.

"Awww, you didn't get to finish yet." Reaching out her hand she gently took my cock in her hand. "Here, let me help."

With a loose grip she started stroking at a leasurely pace. Leaning her body into mine she kissed me and then put a hand on my chest indicating she wanted me lay back on the bed. Doing so she tightened her grip on my cock while she took one of my nipples in her mouth. Licking and sucking my nipples she removed her mouth from my body only long enough to move her head down and take my cock in her mouth in one quick motion.

Focusing on the head of my cock Amanda licked and sucked while stroking the shaft. Stroking and sucking it didn't take long before I felt my balls tighten and my body brace for the impending orgasm. I tried to tell her I was coming but all that came out was garbled gibberish as I felt the first shot of cum shoot out of my cock into her mouth. Based on how amazing my orgasm was I was surprised I didn't blow a hole through her as shot after shot of my cum filled her mouth. Taking it all Amanda continued to pump my cock until I was completely spent.

My body went limp as Amanda finally took my cock from her mouth. I could hear and see her throat muscles working as she swallowed my entire load. With a contented sigh after getting it all down she muttered, "Mmmm, not bad" as she collapsed on the bed next to me. Turning my head to her I kissed her passionately, opening my mouth and allowing her to swirl her cum-flavored tongue with mine. Seeing that I was not afraid of tasting my own cum Amanda continued the tongue kissing until we both had to catch our breath.

"I'm glad you don't mind tasting yourself on my tongue, had I known I would have saved you some." She smiled at me as she wiped a small amount of saliva from my chin.

"I would have liked that. You're right though, my cum isn't bad but yours is downright tasty."

We both laid back on the bed in eachother's arms. Finally every muscle in my body began to relax and I felt a trickle of cum start to leak out of my ass. I thought about jumping out of bed and going to grab a towel to make sure there wasn't a mess but I was too exhausted to move. Between the feel of Amanda's soft skin wrapped around me and warm liquid running down my crack I was fully content and fell asleep within minutes.

Amanda shook me awake when it was still dark outside. I sleepily looked up to see her standing next to the bed fully dressed.

"Hey sleepy head, I didn't want to leave without saying goodbye but it's 5am and I have to go home to get ready for work." Planting a kiss on my lips she turned and headed for the bedroom door. "Thanks for another amazing night, I'll see you soon."

I smiled as I closed my eyes and fell back asleep.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
stopinby13stopinby13about 1 month ago

Hot story, hope it cotinues

AnonymousAnonymousabout 3 years ago
A great start

I think that this is a great story. Amanda seems like a great lady to make your girlfriend, if you like shemales of course!

Durth1Durth1over 7 years ago
good work

Nicely done.

AnonymousAnonymousover 10 years ago
I hope that you will continue the story.

I love the story so far. But I found a bunch of typo and other errors in this chapter. Your first chapter, I did not see many errors. You need to have someone check it over and edit the story before you submit it. But the story was good regardless of the errors.

griffin57griffin57over 11 years ago
Great

Again, a great story! Keep it up. The story that is.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Happiest of Endings A massage with a big, hard surprise.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories