Dory and Jim

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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 almanbahis 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.

We were laughing too. So hard that we were actually convulsing. I steadied myself with my hands on the couch and came up with a coin in my hand that must have fallen out of Jim’s pocket. I was caught up in the mood and without thinking I blurted out, “Heads I win, tails you lose.” Clearly I’d forgotten that I had a secret I needed to share before things went too far.

Jim snatched that coin out of my hand and flipped it high up in the air. We watched it come down and land on the rug before us. It was heads.

I was drunk and I seemed to have no inhibitions around Jim. Again without thinking I said, “Well, coins don’t lie. Heads is head, and I never back out of a bet.” I slipped off the couch onto the floor in front of him. I’d never seen a man smile so much before and it was all because of me.

I rubbed his cock through his pants. He stroked my hair so gently it made my heart melt. But I couldn’t let him find out it was a wig yet, so I put his hands back down on the couch. almanbahis yeni giriş I told him, “It’s my first time doing this. Would you be a Dear and sit on your hands?” I was really looking forward to tasting his cum and he was such a great guy that the idea of sucking an actual cock didn’t seem like a gross idea. I could tell him after.

I really wanted to make him happy. I really wanted him to like me. Maybe if I did a good job he would want more.

I unzipped his pants and fished out his cock, hoping there would be a drop of cum on the tip. I have to admit I accidentally stabbed it with my fake baby-pink fingernail when I reached in. He flinched but was understanding.

When I saw it completely exposed and hard, for the first time in my life I thought a cock was a thing of beauty. Even though I’d seen his once before, last time it was just a source of cum, this time it was an amazing living tube that secondarily was a source of beloved cum.

I figured if I stroked it from base to tip I could work some elixir out. After five or six loving pulls a drop emerged like magic. I wanted to suck it up before it fell off so I pointed his dickhead towards my mouth and pursed my baby-pink lips over the end.

I held my mouth completely still with just the first part of the head of his cock in my mouth. I kept pulling from bottom to top, relaxing on the down stroke and holding firmly on the up. Once I coaxed a few honeydrops onto my tastebuds I couldn’t wait for the whole load.

I’d gotten enough blowjobs from Tory to know what’s good. She knew how to give a good blowjob even if she was more interested in the power dynamics of a relationship than in the act.

This hard cock sticking out of my mouth was going to give me what I craved. But in order for that to happen I needed to give it pleasure too. The arrangement seemed mutually beneficial, the opposite of what Tory made it.

I was going to make love to Jim’s cock. His beautiful cock deserved it and so did he. And why not? He had paid for dinner and made me feel so sexy all night. I was going to give the most beautiful blowjob in the history of blowjobs. Then Jim was going to give me the tastiest load of cum in the history of cum.

I slid my mouth down several inches driving his hard wonderful goo-giving meat into my being, causing Jim’s whole body tensed up as he grabbed fistfulls of the couch cushions and drawing in a lungful of air through clenched teeth. It all came crashing down. Jim held back from screaming, instead hissing, “Eeeeeaww! Whoa! Teeth! Teeth!”

Damn! My first try and I’d scraped my teeth down two sides of his cock. I yanked off suddenly, “Sorry! Sorry! I’ll do better. Oh, can you ever let me suck your beautiful penis again?” I was crying, in mortified fear that I’d hurt the most precious part of him. My mascara ran and my lower lip trembled.

“Oh Dory, this really is your first time. I thought you were just feigning innocence. You know, I’ve had a number of women do that before but none, not a single one, ever had your level of impassioned enthusiasm. You’re a very special girl. Yes, you can try again. Can I, can I use my hands to help you? I won’t force you down, you know.”

“Ok”, I answered. Regaining my composure. “But you can’t mess up my hair. Will you leave your hands out of my hair?” Jim smiled adoringly and nodded. How amazing to be adored by a man! Here I nearly mangled his dick and he adored me. What an amazing man. From my spot on the floor I smiled up, looking into his eyes, “Jim, do whatever you want as long as you watch the hair.”

Jim touched my face gently then slid his hands back around behind my neck, “Is this alright?”

I wiped my face with the back of my hand and grinned really wide so he would know it was alright. I felt slight pressure on the back of my neck and I lowered my head. Jim was talking me through it, “Open wide. Now make it all wet. Use lots of lip but watch the teeth above all else.” I let Jim guide my head up and down. He went slow. My inclination was to bob wildly, to claim my reward, but after my last mistake I needed to trust him.

“Now we want to go as deep as you can without gagging. I’ll pull gently and you tap my leg when it’s far enough.” True to his word he pulled gently causing more of the amazing man’s amazing cock to enter my mouth. When he got to the back I started to worry about what would happen when he came. If it were too far back he wouldn’t drop his cum on my tongue. I wasn’t gagging at all but I tapped frantically.

“Oh, Sorry Babe. I didn’t mean to hurt you. I guess it’s my turn to be careful.”

If he only knew the half of it. I was starting to get the hang of this, but I just let him lead me. Up and down, slowly he touched my neck when he wanted it deeper and I tapped his leg when I worried I would miss the joy juice. Every time I tapped he said he was sorry.

His hips started to lift off the couch. Then he started uncontrollably to hunch up into me. I needed cum so I needed to control the depth. I just kept almanbahis giriş tapping.

He was close. Jim said, “This being your first time I’ll warn you so you can pull off.” He jabbed into my mouth just a few more times when he started yelling out, “Now. Now! NOW!”

This was my moment! His hands flew off my neck and Jim literally sat on them. I could tell every fiber in his being wanted to fuck up into my throat, but he tried really hard to sit still. I sucked as strongly as I could with maybe two inches in me. The perfect depth to feel the incredible sliminess when it came out.

Jim’s body shuddered and he shot several large streams of fantastic jiz in me. Thinking back to that hand job so long ago I remembered he made a lot.

I couldn’t help myself. I pulled off so I could see the rest come out. The last two shots leaped six or seven inches into the air then landed on my hands. I drooled the rest from my mouth into my hands and with great fascination watched it roll around as I held my hands up twisting and turning them to control how it dripped from finger to finger. I tapped my fingers and did a slow motion clap to make long gooey strings.

I scraped as much as I could into the palm of my left hand then plastering my palm to my mouth, sucked all the cum in. I licked off what I couldn’t get the first time, swishing it around in my mouth to feel the essence of it.

Several minutes went by and when I looked up Jim was watching me intently with a sort of perplexed look on his face. What must he think of my display? This was hardly lady-like. My heart pounded in my chest and I must have turned a dozen shades of red.

I jumped up. The knees to my pink stockings were in tatters. The remains of his cum was on my hands and face. Surely, my mascara made me look like a raccoon. Mostly, I hoped my wig didn’t get displaced.

I managed to jam one foot into one high heeled pump and dashed out the door. It was a short run along the river to a more populated area where I caught a cab home. The cabbie confirmed my ragged appearance by his insistence on asking me how I was repeatedly. He didn’t even charge me for the ride. Luckily, when I looked in the mirror at home my wig was just fine.

The light on my machine was blinking: Jim said he had a wonderful time with me, liked talking with me at dinner, thought I was a marvelous and captivating girl, said he wanted to see me again next week, he would return my other shoe, and ended the call by calling me Cinderella.

I fell into my easy chair, satisfied and overjoyed.

Jim and I started seeing each other every week, sometimes twice. For obvious reasons I didn’t tell him my secret that first time and then it just got harder and harder despite my weekly resolve.

We only did blowjobs on our dates and soon enough he would be bound to ask me about that. He never mentioned my unseemly behavior with his cum that first time, or any other time, and seemed to enjoy my cum shows. I just went to the restroom to wash my hands after, and changed the subject when I returned, as if nothing were out of the ordinary.

I always tried to tell him my secret but always chickened out. Jim knew I wanted to share something. He just said when I was ready he would listen.

We’d been dating almost two months when Jim sat me down all serious. I was sure he was going to stop seeing me. Then he started blabbing cutely about kinks.

Jim confessed that he wanted to have sex with a guy, to try giving a blowjob, and my heart jumped when I realized this was my chance to come clean and for everything to work out just fine.

If only he had wanted a guy to blow him instead – then it all would have worked. I offered my ass to him but he was intent on wanting to suck a big cock.

This had all turned so wrong. Here he was admitting to his presumably female girlfriend, who was really a guy, that he wanted to have sex with a big dicked guy – but my dick was only five and a half inches long.

It got worse when it turned out that he had a big dicked guy on the line already. If there was ever a time for me to lose him as my boyfriend now was that time. How much easier would it be for him to reject me if I told him right now?

I was going to have to wait for a better time. Next Jim said that the guy wanted me to come along to watch. Jim told me that he wanted to suck this guys cock because it was 26 inches long. Of course I didn’t believe that. Jim showed me the ad from the guy. It said, “26 inch cock needs sword swallower. First time deep throaters need not apply. If you can’t imagine performing in a circus then you won’t be able to swallow mine.”

I told him that it was obviously just an exaggerated way to describe his dick. It would be very big but no one had a 26 inch dick.

But Jim was obsessed and he wasn’t listening to reason. He was determined to go meet the guy and he wanted me to go along too so nothing bad would happen. Safety in numbers and all..

I was going to have to go. I couldn’t let anything bad happen to my Jim. I didn’t love the idea of seeing Jim suck a cock that wasn’t mine. I imagined that he knew all about me, that he didn’t mind that I wasn’t a woman, and that we lay on the floor 69ing each other. But I couldn’t compete with Jim’s fantasy.

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