A Special Love

Story Info
Claire was more than I expected.
2.5k words
4.59
32.2k
60
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

I'd never claimed to be Mr perfect. I was average looking, had been called handsome by a few women but never really believed them and considered myself average. I still wonder some days how I got so lucky though. Here's me, 5'10", average build, okay job but yet I have a stunning blonde asleep in my bed every night. How it all began is a story I'm going to start at the beginning...

"I need you to work late again Joe, we have 3 projects overdue and 2 people off sick."

I swear my boss hated me, she'd spring those very words on me at least 3 times a month. Being one of very few to ever get the bonuses was the only thing stopping me from just walking and the coffee was good so I mumbled my usual 'sure no problem' and plodded along. Lately there was also the added bonus of the new woman in the office to drool over too. She was tall, blonde and beautiful, pretty much my definition of Goddess and clearly about 50 levels out of my league.

She was fun to talk to though, had a really sweet and soft voice and never seemed to get mad the few occasions she caught me staring at her breasts or her ass.

It was late one Friday night when everything changed for me.

"So, Mr quiet, you never talk about your girlfriend, she not mind you working all these hours?" Said Claire, my office Goddess.

"I've been single for 3 years, little hard to meet anyone when I'm working almost 80 hours a week. What about you?" I replied.

"Oh, no girlfriend at home either." She noticed the smirk on my face and laughed. "I'm kidding, I'm single too."

"How the fu..." I blamed being tired for almost blurting 'how the fuck is a stunner like you not taken' "Sorry, I mean, really?"

"Yup, really. Everyone always seems so surprised at that but I'm really picky and I'm hard to get along with."

I wasn't sure if she was teasing me again, there never seemed to be a moment when she wasn't smiling and hers could light up a room.

"That's fair enough I guess. Well, I'm almost done, do you need help with that last chart?"

"Sure, this one has been a bitch to complete, lets celebrate with some cocktails!"

Was she really inviting me for a drink? I was always one to read far too much into things.

Later that night Claire and I sat in a booth at the bar, both of us 3 margarita's and 2 tequila shots in and having a fun time.

"Sorry folks, my manager said I'm not allowed to serve you any more alcohol, I can bring you a water and that's it"

Our waiter was polite about it, in their defense we were pretty rowdy, Claire was great fun and pretty mischievous when she was drunk, I almost choked on a pretzel when she told a guy she was saving herself to be a nun when he tried to chat her up.

"Well, I know I'm not done drinking. I have more booze at home, wanna join me?" Said Claire, still smiling.

"Uh, ok." Figuring it would be drinks then a cab home I pushed away any thoughts of getting lucky. As we stood up though, Claire grabbed me by the waist and kissed me on the mouth.

"There's no need to be so afraid of me you know, relax and enjoy yourself, I promise I won't bite unless you ask me to."

"I, um.. I'm no good with women, especially one like you."

Claire let me go and put on her jacket.

"One like me, what do you mean?" she replied, frowning slightly.

I was positive she knew exactly and wanted to tease me.

"Well, you're so pretty and out of my reach and...." Before I could say any more Claire softly put her hands on either side of my face and kissed me like I was the last man alive. She stopped smiling and had a serious look on her face as she looked in my eyes.

"Joe, stop putting yourself down, I am far from perfect despite what you think. I like you, you are always polite, you're open minded and nice to people despite how they are to you. Now lets go get some Vodka, I'm starting to dry out here."

The cab ride to her apartment was a lot of fun, she pushed away any doubts I had that she liked me by kissing me the whole way there. Her apartment was nice too, a few boxes were laying still unpacked but her furniture was comfortable looking and she had a good eye for decorating.

"Sorry about the boxes, you'd think after 3 months I'd have them all unpacked but the hours we work I can never be bothered.

While you make us both a drink I'm going to get changed." Said Claire as she headed for the bedroom.

I mixed 2 pretty strong vodka drinks and sat at her counter.

"Sorry, hope you don't mind sweat pants, after the office all week I like to dress down."

Claire had on pink sweatpants and a loose t-shirt but still looked gorgeous to me.

"Hey, is your place, dress how you like."

We only made it through half of our drinks when Claire pounced on me again. Not that I was complaining, I even let the boldness of the many drinks and fondled her breasts through her shirt as we kissed. Claire took my hand and put it under her shirt, letting me have a brief moment of panic thinking I'd gone too far but she wasn't wearing a bra and her breasts were magnificent.

She stopped me when I tried to get between her legs though, moved my hand back up to her boobs with a soft 'too soon'. I guessed the same rules didn't apply for me when she unbuttoned my pants and pulled them down along with my shorts to my knees. Half expecting to wake up I gasped in pleasure when Claire leaned down and took my already hard cock into her mouth, gently fondling my balls as she sucked me.

Her tongue was wonderful and in no time I warned her I was close. It didn't stop her though and I closed my eyes as I exploded into her mouth. Claire only stopped when I started getting soft and looked up at me with a sheepish grin when I was completely spent.

"Enjoy that sweetie?" She said as she helped me pull my pants back up.

"Very much, how about I return the favor."

"Not yet, I like to move at a very deliberate pace, when I'm ready you'll know ok?"

I was still coming down from probably the best blow job I'd ever had so didn't think about arguing.

We spent another couple of hours kissing again, Claire let me suck her nipples and actually gave me head again but I didn't remember crashing out. I woke on her couch with a blanket over me and a very nasty headache. Claire was already up and about, once she seen I was awake she handed me a couple of aspirin and a nice strong coffee.

Weeks went by and our relationship became more than just a fling. The more I got to know her the more I was infatuated by her and I thought myself the luckiest man alive just to spend time with her. I was a little frustrated with our sex life as making love to the sexiest most beautiful woman I'd ever known would have made me so happy.

When she asked me to remove a virus from her laptop I got to find out more than she wanted but I couldn't have been happier and couldn't wait to talk to her about it.

"So, the virus is gone, really tricky bastard that was embedded in one of your movie files. I hope you're not mad but I found your collection." Claire stopped smiling and was going red. "I have to say, a few of them were pretty good but let me give you a better site, especially if the place you got that virus is where the movies are."

"You.... You're not mad or grossed out?" she said, looking at my face for any signs.

"Um, yea, mad at you for the very same porn that gets me off, I have to tell you, I couldn't be happier my dear." I pulled her to me and kissed her.

"Most guys run when I show or tell them about it, are you serious, strap on and she-male porn turns you on?"

"Yes and if I may confess, the domination stuff your bookmarks are all pointing to has me curious too. Please tell me you're the dominant type, I uh, prefer to be controlled."

At that point I thought I'd blown everything, Claire had a look on her face I couldn't decode and tears started running down her face. My heart sank, hurting her was something I never wanted.

"I.. I'm sorry" I tried to say more but Claire grabbed me, held me really tight and kissed my face over and over.

"You have no idea how happy you've just made me. I've never been able to share this stuff with any man. They see me as the sexy conquest and freak out when they actually get to know me.

Are you serious about the she-males turning you on?"

"Yes, most of those videos you have the women are stunning, I've jerked off many a time imagining how much fun it would be to have one to play with."

"Last night on the couch you told me you you were falling for me, did you honestly mean it?"

"I did, I feel like the luckiest man alive to have you. You're beautiful beyond words, you're funny and now that I know you have a mind as dirty as mine, how could I ever want anyone else."

Claire closed the lid on her laptop and without saying anything led me by the hand to her couch.

"There's something we need to talk about and something you need to be happy with before we go any further. I know you have been very eager to fuck me and I hope all the blow jobs have kept your frustration at bay but before we can make love let me show you what you're getting into."

My mind was going in all directions but I had no idea what was coming next. Claire let go of my hands and stood up, facing me.

She took off her shirt first and I was treated to my favorite breasts, then, she slowly removed her sweatpants.

It took a moment to register and then I couldn't take my eyes away. Expecting a trimmed bush neatly framing a perfect looking pussy I was staring at a shaved and very real cock. I didn't know what to say. I'm pretty sure time froze for a while but I was stunned. The blow jobs all made sense now, keep me drained so I didn't venture south but despite having come in her very pretty mouth no longer than 20 mins ago I was rock hard again.

Her cock was as perfect as the rest of her and I was actually a little jealous as she was bigger than me.

"You're killing me here, please say something." said Claire, her face almost contorted in pain.

"Can I touch it?"

It was her turn to be stunned. She slowly walked towards me and sat next to me on the couch, her eyes never leaving mine. She opened her legs for me and was breathing heavily when I started to stroke her. I felt it grow in my hand and guessed her to be at least 8 inches and pretty thick. I kept stroking her gently and kissed her passionately.

"How did you manage to keep this hidden, you're bigger than me!"

Claire giggled, her smile finally returning to her face.

"Low cut tops sweetie, you're pretty easy to distract with cleavage."

I still couldn't believe I had gotten so lucky. I guess mostly to my own surprise I leaned down on the couch and took her cock into my mouth for the first time. I'd never done anything like it before and didn't give a damn what sucking this sexy woman's cock made me but I loved her more than life by that point and did my best to emulate the things she did to me with her mouth. When her beautiful sweet voice moaned "I'm going to cum" I couldn't have been more turned on and sucked harder, circling the head of her cock with my tongue. A few seconds later I was rewarded by spurt after spurt of her seed and did my best to swallow as much as I could. When she got too sensitive she pulled me up to her face and kissed me, licking the cum that had escaped my lips.

"You've made me the most happy woman alive, come to bed with me, I want to give you something." Said Claire, gazing into my eyes.

I watched her ass as I followed, my cock still hard from sucking her.

Claire reached into a drawer beside her bed and pulled out a bottle of lube and after pulling me up onto the bed with her, poured some into her hand and coated my cock with it. She then pushed me onto my back and fed my cock into her ass, taking it slow until she had all of me inside, her balls resting on my pelvis. She rode me slow and deep, her beautiful tits swaying in my face as she leaned forward. She got up and had me enter her from behind and I took hold of her hips as I fucked her, watching her tits and cock swing in the mirror with each of my thrusts. Claire was wonderful and tight so I didn't last as long as I'd wanted to but it felt good, pushing in deep as my cock spurted what was left in my balls into my woman.

As the weeks went by my life took a pretty wonderful but surreal turn. Claire asked me to move in with her and we worked on our lives together without fear of any surprises. She told me about her past, moving cities every few years, told me about her transition, being very feminine made it easy for her (apart from her big cock).

She slowly introduced me to some of her friends too, most of them women who loved being fucked by her. She even lets me fuck a few of them when she's there, a reward for taking her monster cock in my ass but a lot of the time I just do as I'm told and enjoy every second.

As for the office? We both quit at the same time, took jobs with normal hours and have a lot more time to enjoy each other.

I look over at Claire again and she's smiling at me, I know that smile all to well.

"Yes Mistress, I'll stop writing and get the lube for you."

It's going to be a great day.....


Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
510mike510mike11 months ago

Lovely! I'd love to trade places with him!

AnonymousAnonymousabout 1 year ago

Pretty good but I hate that he turned gay.

AnonymousAnonymousover 1 year ago

I enjoyed the story quite a lot, even though it needed a bit of proofreading.

However, I feel it would have been much richer with a more detailed description of his first experience with sucking a cock. Having his senses - and ours - involved is what true erotica is all about.

Nicely done, though.

BrokenQuillBrokenQuillover 2 years ago

Great story! I loved the way it became more than just sex, and became a love story in the end.

jrrtolkien420jrrtolkien420almost 3 years ago

Great story!!! Would love to know what became of them?

Show More
Share this Story

Similar Stories

Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
More Stories