Author: CuteJessica1989

A daydream [TM][gangbang][cuckold]

This is a daydream I had. So that makes it fiction which is why I post it here.

A little background story: My FWB recently turned into my boyfriend. I am an unouted crossdresser. This is the first time I am out in public. I’m watching my boyfriend’s soccer team dressed as a basic bitch. Sunglasses, jeans, boots. You get the idea. There are a lot of cute guys (25-30) on the field. I mean, they are sweating and competing, that’s kinda hot. One of “my” team’s teammates had a dick that was clearly showing through the shorts. The silhouette was easily visible. That got me dreaming…

After a hard match the team was still chatting on the field. I sneaked into the locker room to suprise my bf and to congratulate him on the great job he did out on the field. He was drying himself after the shower when I found him. His face had a look of “what if someone finds us, knowing full well that the rest of the guys would inevitably show up. I just smiled and put m1y finger on my lips “hush, you did such a good job out there. You deserve a reward” I took his towel, put it aside and started to blow him on my knees. He quickly grew inside of my mouth. The inevitable eventually happened and the team came in, only to see me on my knees servicing one of them. Read more »

More! How I spent Saturday in bed, getting thoroughly fucked. [TM]

Brace yourselves, wall of text incoming.
Seriously, it’s a fuckload of text.

So, last Saturday I did something I hadn’t done before. Let’s start at the beginning

7:30 (-ish)

I get up. The man in my bed is still asleep. He’d better be, because I sucked him to sleep yesterday. To the bathroom I go to freshen up. I feel horny and prepare myself. The night gown is being switched with a new fresh one. I climb back under the blanket and start nibbling on the man’s soft cock. It quickly starts to grow and commence sucking. Alex is gently woken by the sensation of being mouth milked. “Shush, keep sleeping” I tell him jokingly.

“Bu..” I interrupt his ‘but’ by cranking up the sucktion to subject him. He complies.

Since he’s already hard and in bed, I jump on his dick facing him. I gently grab his hands, smile at him and start to ride him slowly, enjoying the sensation of making him enter me at my command. Soon be starts thrusting his with his hips. His wish is mine as well and start to slam myself down on him. I bend down to kiss him and guide his hands down my thighs. I lean on his chest and increase the speed. He splitting me real good now. Soon I cum quietly, my mouth opened for a silent scream. My asshole’s twitching kicks him over the edge as well and he floods me with his cum. Read more »

More! My boyfriend and I discover my hidden desires [TM]

Edit: wall of text

TLDR: I’m a whore for the right guy.

Quick recap:
The guy I’m fucking on saturdays(Alex, not his real name) booty calls me and I think I fell in love. Also: steamy sex. He’s lingering around and sort of not leaving. He blew a load in me and we just had breakfast.

Alex asked what I normally do now. I answer  “grocery shopping, then getting ready to come over and see you”

“Well you already ‘saw’ me so i’d say it’s groceries, huh?” I don’t know what to say because I haven’t been out as Jessica yet because of the possible fallout. But I also want to look good in front of Alex so I hesitantly get my list ready. Funny how such a mundane task could make me so nervous. “Can we please drive to the supermarket two towns over?” I ask timidly.

“Do you have coupons from them?” I just look at the floor embarrassed. 10 minutes ago I told Alex to fuck me on the kitchen counter and now I couldn’t get a word out. I felt so stupid. 

“Oh… is it because you…?”

“Yeah…” Read more »

FWB turned boyfriend [TM]

Brace yourselves! Wall of text incoming.

Background: I visit Alex for Sex on Saturdays.

TLDR: kinda ruff sex turns fwb into boyfriend (I think)

The following happened 2 weeks ago.
It was about 3 at work when I received a text message from Alex:
“Tonight”

I replied:
“Come over at 7”

Alex is the guy I’m seeing on Saturdays he’s a sweet guy. I’ve written about one of my encounters with him on this sub. We always had this unspoken agreement that if one of us needs to see the other for “sexy time” we wouldn’t turn it down.

His next message read:
“Can you do the thing?”

I replied:
“? yes I can do the thing ?”

The thing was his schoolgirl fantasy. Sitting at work with anticipation of serving him this night was almost too much. I couldn’t wait to hurry home. On the way home I bought white knee high stockings. I had a heavy grey chequered mini skirt that was just waiting for this occasion. The obligatory white blouse and pointy white High Heels concluded the outfit. Underneath I wore my favorite red G-String Set. Getting ready took me about an hour and suddenly it was 6:30. I took a quick few provocative selfies and send them to him. Read more »

[M]y first (and las[T]) big dick.

It’s been a while since my last post.
This one is about living out my fantasies and biting of more than I could swallow ( figuratively speaking).

Edit: wall of text.

One of my fantasies is Cocks. BIG Cocks.
I went looking for a guy with the proper schlong, but since it’s me it took about 6 months until I found someone I vibed with and who didn’t flake or did drugs or was a creep.
Let’s call Mr. Big “Joe”. I’ve found him online and he had a thing for “girls” like me. And he also had an absolute unit he commanded with his loins.

7.5″ long 1.5″ wide and circumcised with a pointy head. Also, he was 6’1″ and was a highschool wrestler. He still had that brawly vibe

We skyped back and forth and finally found a date that worked for the both of us. I wanted it to be special for me so I shopped for some lingerie for the occasion. White garter belt, white stockings a lacey white g-string and a fitting corsage. So the Friday arrives and it’s 7Pm when I’m still getting ready. The doorbell rings and I let him in, wearing only a blue shift dress, the set and high heels.
He immediately checks me out and starts grinning. He even brought me a flower. A dandelion he picked from the frontlawn. Read more »

Strong independent “Woman” [TF]

First time, mobile phone.

I’m a slut and I love it
I’ve [M29] been crossdressing for quite a while and half a year ago I finally had the guts to start having sex and embracing my lifestyle a little more openly. I’m still scared shitless that my boss or my family are going to find out. But a “girl” has needs.

Now I don’t just jump on cocks. I just can’t do it, I don’t have it in me. I have to build a relationship and trust the guy to some degree.

Since dressing up and getting ready takes effing long I mostly do it on the weekends.

Here’s my craziest day: Every Saturday I dress up and visit one of my guys in his appartment. We ended up agreeing on one visit every Saturday. That’s a long story….
Here’s the deal: I come prepared and ready to go, ring the bell and he waits for me naked in his living room. I get rid of my coat or jacket or whatever fall to my knees and blow him until he’s hard. Doesn’t take long. He then chooses whatever furniture he likes and fucks me on it. The wall, the couch, kitchen table, we’ve done em all. Here’s the kicker we both don’t say a single word. Once he’s done I readjust my clothes and leave without looking back. At this particular day I also had a dinner date plannend. Read more »

A Captivating Night [TM]

Tldr: i tried my cuffs for the first time.

This fond memory happened on a Friday night.
I met my lover (let’s call him Alex) online, we chatted back and forth and this was going to be the first date. It looked good on paper. And as I would later find out he looked good in Person too. 5’11, light tan, cute face, he was in shape, white buttoned down shirt black ironed pants. Yummy.

I wore a ruffled rose blouse, dark blue office skirt, white bolero jacket, black stay ups, a pink bra and a matching thong. Hair was open, smokey eyes and beige lipstick. This girl was dtf.

He arrived. When I let him in he had this killer smile and I knew right away that he would get lucky tonight. It’s still awkward though because I can’t think of anything else other than smalltalk.
I brush his shoulder to direct him to the couch. This sucker had SHOULDERS! We continue talking about hobbies and his hand starts caressing my thigh. I was still wearing the skirt and he basically went for the bullseye. And he kept talking as if nothing had happened. So I move a little closer put his hand back and start grabbing his package. “Tell me more about” yada yada yada who cares. Read more »