Dory and Jim (Part 2)
Part 1 is called "Dory and the Guy Who Claimed to Have a Twenty-Six Inch Cock"
This story contains a spoiler so it really is best to read the first one first unless you have no intention of reading the first one at all. I'm sorry to say that the audience for the two stories might not be the same.
This is one of those times where the same story is told from two different points of view. They are not parallel because the characters have such different thoughts.
So here it is:
Hi. My name is Dory. I blame my mother for that. I blame her for a lot of things. She wasn't a very good mother. My full name is Dorian but given the infamous history of that name Dory is the better moniker.
This is a story about cum loving, cross dressing, and my boyfriend Jim.
Growing up my mom used to compare me to my sister all the time. And not in a good way. She would constantly say things like, "Why can't you be more like your sister?" Or "Your sister has such pretty hair, why can't you do something with yours?"
Up to the age of four she sometimes dressed me in my sister's clothes. But when the neighbors complained about her dressing her son in girl's clothes she stopped - and then blamed me.
**
My first year of college, and I assume unrelated to the first part of my story, I developed a fascination with my cum. I used to cum in my hand and play with it: Spreading it around, making sticky strings, and even tasting it.
Things really progressed when I came back to my dorm one day and my roommate had left a pair of his underwear on his bed with the remains of his last orgasm. It looked just like mine, and there was so much of it.
Gingerly I picked up his underwear and looked at it closely. I hadn't intended to smell it but it was right there under my nose. The odor intrigued me so I stuck my finger in it. Then with my first finger and my thumb I tapped them against each other which was my favorite way to make cum strings. And that was the very instant I realized playing with anyone's cum was just as much fun as playing with mine.
It wasn't more than a couple of minutes later that I decided to taste it. Why not? No one would know. If you can believe it, I didn't debate with myself about whether I should taste it or not, I debated about whether I should scoop it up or lick it up.
If I scooped it up I would only get little bits at a time. But if I licked it up my tongue would come into contact with underwear that had come into contact with his penis. Licking cum didn't seem gross at all but licking his underwear did.
In the end I wanted to savor the entire wad of cum all at once so I stuffed the wet gooey spot into my mouth and licked and sucked all the cum. I loved every drop. As soon as I was finished I lay down in my bed to jerk off and play with my own.
He was my roommate for two years. He must have figured it out at some point when the cum in his underwear always vanished. I imagine that he must have been leaving the cum presents for me.
**
In my last year of college I dated Tory. She was the same height and build as me - tall and slim. Mousy but cute brown hair, perky medium breasts with pointy brown nipples, and a freckled pixy button nose.
I felt like I could share everything with her, all my deep feelings, dreams, and secrets. I shared my delight in playing with my cum. I would have shared how I had played with Stephen's too but it was in the past, I think deep down I also knew not to trust her with that.
She claimed to understand my kink and convinced me that if I liked cum I must have a secret desire to be a girl. Tory encouraged me to wear her things when we had sex and even under my own clothing. We had a lot of fun with it, but in the end when she broke up with me she cited that as the reason.
**
After college I kept playing with my cum and kept dressing up. The two did seem connected in my mind. I got creative with both.
One night I was on the internet when I learned I could meet guys who also had unusual interests or whatever. That night I met Jim, who becomes the major part of this story later.
We both drove over to a secluded parking lot where I got into his car. I wasn't dressed in my girl clothes because I didn't leave the house in them at that time. We were both nervous so we talked for a long time. I learned a lot about what motivated him and made him tick. Finally, I jerked him off and played with and ate his cum as we agreed I would.
That was the only and last I saw of Jim for a year.
**
I continued dressing up, discovered porn videos featuring actors who dressed, and even went outside while dressed - at night anyway. It wasnt that I wasn't passable - I am. In fact, not only am I passable but I'm hot. I only went out at night because it takes a lot of courage.
At first I thought if I went out with a friend who was also dressed I could do it. I thought about that a lot. But the more I thought about it, the more I wanted to go out on a date and be treated like a lady. The idea of being treated like a lady became my driving motivation.
I tried a singles app but in the end it wasn't for me. There wasn't even a category for me. Then I remembered Jim.
How to approach him? Do I just call and say what I want? Would I keep jacking him off, or would he want a BJ? Was I ready to take a cock into my mouth? Would he only want hookups like the other time or would he even be willing to date a crossdresser?
I decided a phone call was the best way to initiate, but I couldn't find out what his number was. You may remember that we had talked a lot on our last encounter so I could figure out where he lived based on his description of the house and neighborhood.
I decided that the only way was to stop by, unfortunately, unannounced, and just lay it all out there. One Saturday morning I headed over dressed to kill in my most attractive feminine clothes, but I lost my nerve and just went to a new coffee shop around the corner.
I was waiting in line when the guy behind me told the barista that my drink was 'on him'. No one had ever bought a drink for me before and I felt the most incredible feelings to finally have it happen. Turning to thank my mystery man it was none other than Jim. I was near his place, on a Saturday morning, so it wasn't an impossible coincidence but it still caught me off guard. I could have even planned to meet him like this, but how many Saturdays would I have had to drink here before we ran into each other?
I had so many plans and ways to tell him and they all went out the window. All I could do was thank him but I couldn't even get that out. Jim was so confident and assertive that he just took me by my hand and led me to a table. What a man!
We talked for half an hour. He was charming and entertaining and easy to talk to - just like that time in his car.
I gave him my number hoping to all hope that he would call. And he did! By lunch time the same day we had our first date set up for that night.
I spent all afternoon waxing, plucking, choosing the perfect outfit, and preparing my speech for when I told him I was that guy from last year. I would do it in private. I was so horned up thinking about when I ate his cum. When it was all said and done, if he asked I would do it on our first date.
He took me to watch some people fly giant kites in the park, then to dinner at a trendy new restaurant, then for a walk along the river. It was totally romantic, something I didn't know I would like until I experienced it, and he was a perfect gallant gentleman. I was on a real date being wooed like a real lady. I was in awe of him and I never wanted it to end.
We were throwing leftover bread from our doggy bags to the ducks when he said he lived just a few hundred feet away and we should go get our leftovers in the fridge. Looking around I could see he was right. I must've been turned around because I didn't realize we were so close. His place would offer the perfect opportunity to tell him.
On the walk over we got to talking about dirty jokes we both watched on Youtube. I guess that's something else we had in common in addition to so much else we had connected over on our date.
He made us more drinks and he said he heard a really funny one the other day but couldn't remember it all. He wanted to look through the history to show me. He found the video and we watched it to find that joke. He was right, it was really good and we both cracked up.
We were sitting on the couch with his arm around me laughing. I'd never felt so close to another human being. The first video was over and another one started automatically. This video was all about guys using cheesy pick-up lines and the reactions from the girls. At one point the guy in the video approached a woman saying, "Let's flip a coin. Heads you go down on me, and tails I go down on you." It was so bad! And the girl wasn't foolish enough to take the bait. She just laughed in his face.
