Caught with Consequences Ch. 02


As I was dropping her off back at her office, Becca said, "Do you feel like going out and getting a couple drinks after work tonight?" If I didn't know better, I'd think she was asking me out!

I said, "Yeah, that sounds great!"

She said, "Cool, I'll swing by around 5:00 and pick you up." and then she leaned over for a little hug...only when she did, I thought she gave me just the slightest peck on my cheek at the same time.

I thought, "Dang, did I just imagine that?" In any case, as I drove back to my office, I was getting obviously worked up thinking about it, judging by the bulge in my skirt! I had to sit in the parking lot for a while before I could get myself calmed down enough to get out of my car.

As I sat at my desk, all I could think about was, "I can't believe I let my life get turned so upside down. Four days ago, I had to start wearing a dress to keep my job. Three days ago, I spent most of my day on my knees sucking cock, swallowing cum, and getting mercilessly fucked in the ass. Now I've met this incredible girl who seems like she's into me, only she doesn't know who the real me is. Damn, I'm an idiot!!"

I was lost in my thoughts when Natasha called me into her office. She was sitting at her desk and she was clearly in some discomfort. She told me that her neck and shoulders were really bothering her as she was trying to rub one of her shoulders herself. She then said, "Stephanie, would you be a dear and rub my shoulders a little for me please?"

"Of course I will," I said, and I walked over and stood behind her. I gently started to rub her shoulders and neck, and as I increased the pressure, she let out the sexiest moan I'd ever heard. For the next minute or two this continued, with her telling me several times how great it felt. Then she asked me to stop, and to go close the door. As I did, she got her yoga mat out of her closet and unrolled it on the floor.

She said, "I think I can relax more if I'm lying down as you work on my shoulders."

"Yeah, that's probably true," I said. Then she did something very much unexpected, and started to unbutton her blouse.

She could see the shock in my face, so she said, "Don't look so surprised, you should know I don't want my blouse to get all wrinkled." With that she slid her blouse off her shoulders, revealing the most beautiful white lace bra I'd ever seen. She handed me her blouse, and I carefully laid it over her chair, and as I turned back towards her, she had already unzipped her skirt and was wriggling out of it, revealing matching panties. She handed me her skirt to put with her blouse, as she laid face down on the yoga mat.

I knelt beside her and tried to resume the shoulder massage that I started before. My hands were trembling! The woman that I had adored and secretly lusted after for the last 11 months was lying next to me in nothing but her bra and panties, and she's expecting me to massage is looking up again! Again, as I rubbed her shoulders and back, she continued with her sexy sighs and moans, telling me how great it feels. This is almost too much!

I continued massaging her shoulders, but ever so slowly started working on her upper back. She continued with her sighs of approval, so I kept going. I moved to her middle back, just below her bra strap, which she clearly still approved of. I then moved to her lower back, and my fingers then brushed the lace of her panties. She was quite, but she didn't say stop, so I started rubbing the backs of her legs, all the way down her calves and back up to her lacy panties. As I gently brushed over her beautiful lace covered ass, she slowly ground her hips in a circular motion and slowly parted her legs, just a bit.

I couldn't stop myself, so I slid my hand gently down the crack of her ass, between her thighs until I felt the warm dampness of her lace covered pussy. Her sighs and moans were much more pronounced now as she was getting more and more worked up, then with saying a word, she rolled over onto her back. My hand went directly back to her pussy, as I lightly dragged my nails of my other hand over her firm, toned belly. She undid the front clasp of her bra, finally giving me a view of her prefect tits. She looked me in the eye, but didn't have to say a word. I leaned in and took one of her rock hard nipples in my mouth, as one of my fingers wiggled its way inside her pussy. After another minute or two, again, we locked eyes, and again she didn't say a word as she slowly pushed me down her beautiful body.

I slid down her body till my face was between her thighs. I slid her dainty lace panties to the side, revealing her sopping wet pussy, and slowly worked my tongue up inside her. She wrapped her thighs tight around my head, and I felt the heels of her stilettos digging into my back. Her sighs and moans turned to breathless exclamations of, "YES, OH STEPHANIE, YES, YES, YES!!!!"

She was grinding her pussy harder and harder into my face, as I was now moaning and begging her to cum for me. I then felt her thighs start to quiver, as she yelled even louder, "OH STEPHANIE, I'M CUMMING, OH YES, YES, YESSSSSSS!"

I could feel her pussy throbbing as waves of orgasm tore through her entire body. I greedily licked up every delicious drop of her sweet delicate cum, as her orgasm slowly subsided. As I laid there with my face held tight to her creamy pussy and her stiletto's digging into my back, I felt like the luckiest....uh...girl, in the world! After a minute or so more of me nuzzling her sweet pussy, we locked eyes and stared at each other for a few seconds. Natasha then said, "I need to update your job description, and add that to it. We'll call it "Other Duties as Assigned!""

With that, she unwrapped her thighs and released her sexy grip on me. As I sat up, she ordered my to lay on my back on the yoga mat. As I did that, she hiked up my skirt, and pulled off my panties, then pulled off her own panties, and straddled my thighs. She slowly inched her way up my body until her delicious pussy was directly over my throbbing cock, and she ever so slowly lowered herself onto me. I let out my own girly sigh as I felt her pussy massaging my cock while she was grinding her hips on mine.

Then she leaned down, and gave me a slight kiss, put her finger to her lips as if to say "SHH" and then she sat upright. As she started to ride me, I could feel my cock slide almost all the out, then completely bottom out again in her luscious pussy. Natasha leaned her head back and she was biting her bottom lip. Her beautiful, full tits bounced in rhythm as she rode me hard, thrusting her sweet pussy down on my cock over and over. It was a sight I'll never forget! Even though she motioned for me to be quiet, I couldn't stop myself from making girly moans and sighs, and they fit right in with all the sexy moaning coming from her. After a few short minutes, I just couldn't hold out any longer, so with a muffled squeal from me, my cock erupted. Natasha's pussy took wave after incredible wave of cum from my spasming cock.

Even after the waves ended, I could feel her pussy milking my cock of absolutely everything I had. As I laid there admiring Natasha's glistening, beautiful body, again she playfully put her finger to her lips, to silently say "SHH", then she slowly started to move. As I felt my now shriveling cock gently slip from her pussy, she kept moving up my body until her pussy was directly over my face. Once there, she relaxed her pussy, and a steady stream of my cum dribbled from her pussy into my mouth. I gladly gobbled it up as she made sure to give me every creamy drop. I was sure to lick her pussy completely clean, and give it several long slow kisses before she unstraddled my face.

As we both sat on that yoga mat for a minute catching our breath, we didn't say a word to each other; we just sat and smiled at each other. Finally Natasha broke the silence by simply saying, " That was incredible Stephanie!"

All I could say was, "It certainly was!" I really wanted to tell her that I'd wanted her since the day we met, but I figured I shouldn't push it. There are some things a girl should just keep to herself! I watched as Natasha got herself dressed again, and we both cleaned ourselves up. My make-up was a smeared cummy mess, so I took it all off and re did it before going back to my desk.

We spent the rest of the afternoon working. We had several projects going, so we had lots of files scattered around the office. About 4:30, Natasha said, "Well, that was quite a productive day, but I need to take off. Please be a dear and straighten up these files before you leave, OK?"

"Of course," I said, "No problem at all. Have a great evening, and I 'll see ya tomorrow." And with that, Natasha patted me on my ass and we exchanged sexy smiles as she headed out the door.

Just after she left, Becca walked in, and she looked HOT! She was wearing a plaid pleated skirt, and a soft dusty pink sweater. As soon as I saw her, all I could say was "WOW, you look amazing!"

She responded, "Aw, thanks, you look super cute today too! Are you ready to do this?"

"Yup, just give me a few minutes to put all this stuff away."

Becca sat up on the edge of Natasha's desk as I was gathering files and putting them away. She just watched me as I walked back and forth to the cabinets. Every time I walked by her, I could smell her sweet was so intoxicating! I wanted to be closer to her, so I mentioned again that I loved her outfit, and then I stopped right in front of her. I reached out to touch her earrings as I said, "I really love your earrings, where did you get them?" While I was touching her earring pretending to admire it, Becca grabbed my shoulders and pulled me in to her and gave me a deep, passionate kiss. While it completely took me by surprise, I certainly didn't try to stop her!!

The kiss probably lasted for 15 seconds, before we pulled back and just stared into each other's eyes. Our lust for each other was obvious, and again, we started kissing. It was the longest, hottest, wettest kiss I've ever experienced!! As much as I liked it, and wanted to continue, I knew I had to tell her the truth about me before she found out herself...I just didn't know how do it.

Again, we were just looking into each other's eyes, and I said, " don't know if we should be doing this."

"Why not? Don't you like it?"

"Of course I do!! No, it's not that at all...I think your friggin' awesome! It's just that...well...I'm not exactly...I'm not quite who you think I am."

Becca looked at me and said, "Steff, don't worry about it, I already know!" and she reached down and gently brushed her hand against my panty covered cock.

I said, "YOU KNOW? How did you know? Did Natasha tell you?"

She said, "No, Natasha didn't say anything. Yesterday after lunch, when I gave you a hug, you had a cute, but obvious bulge in your skirt."

I said, "And all this doesn't creep you out?"

Becca said, "No, not at all, I find it adorable! And by the way, you're a very convincing girl, you sexy little thing!" and with that, she pulled me in for another hot kiss.

Since she was sitting on the desk as we were kissing, she wrapped her legs around me and pulled me in tight. Becca was so beautiful, and all this felt so good. She was grinding her pelvis against my cock, and making little moans as we were kissing. As that kiss broke, Becca didn't say anything, but she gently pushed me away from her a bit and looked down. My eyes followed hers, down past her beautiful tits, and imagine my surprise when I noticed that she had an obvious bulge in her sexy little skirt too!

I looked back at her face as she gave me a sexy grin, then back at her tented skirt. She slowly, but playfully lifted the hem of her skirt and revealed her beautiful 6 inch cock, encased in black lace panties.

The only sound I could make was "WOW!" as I instinctively sunk to me knees. I just stared for a few seconds before I nervously reached out and took her cock in my hand. I gently started stroking it, playfully dragging my nails from her balls to the tip. A drop of pre-cum had formed, so I leaned in to lick it up; it tasted so sweet! As I looked into Becca's eyes, I took her cock in my mouth. With my pretty pink lips lovingly wrapped around the head, I slowly took it straight to the back of my throat while also massaging the sensitive underside with my tongue. After a minute or two, Becca pulled me back to my feet for another hot kiss. As we were kissing, she stood up and had me get up on the desk. When the kiss broke, she told me to lay down on the desk as she hiked up my skirt.

Becca said, "Oh Steff, your cock is beautiful, and I love your sexy panties! There's just nothing better than a pretty girl with a cock, wouldn't you agree?"

As Becca leaned in and took my throbbing cock in her mouth, she slipped off her panties and climbed onto the desk positioning her own dripping cock directly over my mouth. She slowly lowered herself until half her cock was in my mouth. I greedily sucked on her rigid meat, and took as much of it in my mouth as she would let me. At the same time, Becca was rhythmically bobbing up and down on my cock, easily taking my entire length clear into her throat. It was an amazing feeling, which I certainly wanted to reciprocate.

Becca slowly began pumping her hips, forcing her sweet cock deeper into my mouth, touching the back of my throat. Before too long, she was thrusting her entire length into my cock hungry mouth. Over and over, I watched every inch of her saliva and pre cum covered cock pump in and out of my mouth, her heavy balls hit me on the nose with every stroke. I felt her rigid cock invade my throat and her pelvis slap my chin every time she bottomed out. The sounds of us slurping on each other's cocks, coupled with our increasingly loud moaning were nothing short of incredible, and were almost too much for me to handle! After just a few minutes of this, I just couldn't hold out any longer, and my cock erupted in Becca's mouth.

If I could have screamed in ecstasy, I would have, but that's tough to do with a mouth full of a beautiful, luscious cock! Just as my orgasm was subsiding, I could feel Becca's thighs start to tighten, and soon she unleashed an absolute torrent of cum into my mouth. We were both almost motionless for a minute as we milked every creamy drop from each other, then Becca climbed off me and I sat up. We immediately leaned in and kissed each other, each with a mouth full of cum.

As we kissed, our tongues swished and swirled two enormous loads of warm gooey cum with each other. As our lips separated, strings of our creamy treats stretched out between us, then broke and clung to our chins. We each giggled, then after we each swallowed that sweet cummy mixture, we took turns wiping off the dribbles on each other's chin and seductively licking our fingers clean.

After we put our panties back on, and spent some time fixing our make-up, we straightened up the office a bit, and then headed out to go get some drinks. At the bar, I explained the whole situation to Becca. I pointed out that while I was still really nervous going out in public dressed as Stephanie for fear of getting outed as a dude in a dress, at the same time, I was also beginning to enjoy the experience more and more...especially all the additional duties Stephanie has!

Becca explained that once she hit puberty, regardless of what her body was doing, she felt like she was more of a girl than guy. She started wearing girl's clothes in private whenever she could, and after a few years of hiding it, the feelings grew so strong that she started adding women's jeans and shirts to her everyday wardrobe. Once she graduated high school, she moved away to college, and started dressing as a girl full time. That's when she also started low dose hormones. I asked her if that's how she got her beautiful tits, she cupped them with her hands and said, "Oh no sweetie, I bought these! Dr. Cunningham in St Louis does awesome work doesn't he?"

I asked her if she was going to get more surgery to complete her transition, and she replied, "Hell no! I love my body just the way it is. Like I said before, there's nothing I find sexier than a pretty girl with a nice cock!!"

We finished our drinks and headed out of the bar holding hands. Outside, we gave each other a sweet, passionate kiss while we groped each other's ass. Becca said, "Hey Steffie, I'm headed out of town tomorrow and I'll be gone for a couple weeks, but when I get back, I would really love to see you again!"

"I would love that Becca!" And with that we both got in our cars and headed home.

I only have a few weeks left until the internship is done. I had thought that once it's over, Stephanie would go away, but now I'm not so sure...

Report Story

bySteffinheels© 3 comments/ 20471 views/ 29 favorites

Share the love

Tags For This Story

Report a Bug

2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartEnjoyBoth, Joann69 and 27 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by EnjoyBoth03/13/19

Enjoying the Consequences

Yes, I'm reading through the series and am drawn to how well you have described the characters and their actions. Would loved to have known how Steph dealt with neighbors and the transition. Regardless,more...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 3 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: