Kate

The story does not contain sexual activity involving people under 18.

*****

The day Daisy agreed to go out with me was the happiest day of my life. I was 5'6" and she 5'2", so we matched very well. I loved her red hair, green eyes, mischievous smile, and her thin body frame with B cup perky tits. I saw us finishing college, getting married, having a daughter and a son, and living happily ever after. Our chat and sense of humor fit each other perfectly.

If there was something that could have been better, it was our sex. I could easily cum from watching Daisy's naked body, touching it, sucking her reddish nipples, and having an intercourse. However, I got the impression that on multiple occasions, Daisy did not orgasm. She always smiled and assured me it was no big deal, but it had to be frustrating. She never complained, but I knew that my thin, 5"-when-erect dick had to do with it. I tried to ignore this issue, thinking sex was not the most important thing in life, and since everything else was optimal, our life together would still be fantastic.

Boy, was I wrong. A day after my 22nd birthday, which happened to occur as the summer vacation started, she was in my room and rather than undress as she usually did in the past, she blurted, "Tommy, we need to talk."

"Yes honey. What's on your mind?"

"I am leaving."

"What do you mean 'leaving'?"

"I am stopping being your girlfriend."

"... what? why???..."

"Look, sex with you is no fun. I attempted to ignore it and satisfy myself with my Jack Rabbit, but it's a short term solution. Then, 2 weeks ago, Robi saw me upset and stayed with me to comfort me. To cut the story short, he hugged me, we got excited, and had sex together. Being fucked by a real man taught me what I was missing being with you. After our escapade, he apologized for taking advantage of my vulnerable state and said he would be honored if I agreed to go out with him. Tomorrow I'll tell him I agree to date him. So we are over."

I looked at her with tears in my eyes, "So all the time we enjoyed together means nothing to you?"

She placed her palm on mine and muttered, "It's not 'nothing', but I cannot deny my body the full benefits of physical bliss. I'll always remember you as my nice, first boyfriend." And then she left. I was stunned, cried my heart out, and decided to go to a bar to get drunk.

...

The bar was half busy. I ordered a combination of vodka and rum. The barman checked that I was over 21 and did what I requested. I found a corner table for two, sat down, and chugged the glass contents. Ten minutes later, I asked for another one. My prior experience with alcoholic drinks was minimal: I drank beers only 3 times before, and tasted vodka once. My inexperience, coupled with not eating before coming to the bar, made me start losing it after 20 minutes. With tears pouring, I was thinking over and over what I did wrong that Daisy chose to leave.

My vision became blurred, but I could still see a pretty woman glancing at me nonstop. After a few minutes, I forced a little smile at her. She moved toward my table. She was tall, about 5'9", with brown, shoulder length brown hair. She approached me and asked in a deep voice, "Do you mind if I join you?"

I stuttered, "Iit's a freee country."

She sat by me and said, "I noticed you were crying and trying to get drunk. You obviously suffered a traumatic event. Care to talk about it?"

"Noobody can heeelp me now, Daaisy is gone foreever."

"Who is Daisy?"

"She waas the love of my life, aand decided to leave me for Roobi."

The lady put a large palm on mine and murmured, "Honey, it's her loss. I can see that you are a nice boy and deserve to be loved."

My tears began dripping again, "I knoow, but I feel teerrible."

She looked around. The place became cramped and noisier. She said, "My name is Kate. I feel for you. It's too loud around here. I live across the street. Would you like to accompany me to my place and tell me all about it?"

"... I doon't knoow..."

"You are drunk. I'll give you coffee with some cookies, and let you relax on my bed. This will make you feel better. And if at any time you wish to talk to me, I'll be available."

I attempted to stand up but lost my balance. I was fortunate that Kate caught me before I fell down. She helped me wobble to her small house and sat me on her sofa. As she walked to the kitchen to make coffee, I watched the pictures she had on her living room walls. All of them had a common theme; they showed half naked bodies of guys and girls in various poses. I was light headed, but despite my less-than-clear mind, the eroticism oozing from the pictures was obvious.

Next, Kate arrived carrying a tray with 2 coffee mugs and several cookies. I grabbed my mug, but almost dropped it. She grinned, lifted my mug, and placed it before my lips while hugging my shoulder with her other hand. Her firm breasts pressed against me, coupled with her strong floral scent aroused me and my penis began to engorge.

Kate puckered her lips to signal to me to open my mouth, and then she gently poured some of the coffee into my mouth. Her red shiny lips looked very tempting and soon, my dick was at full mast. I cared less about the coffee than the effect she had on cock and psyche.

Kate continued helping me with the coffee and realized there was a small tent in my pants. She smiled, "I am happy to see you've noticed Daisy was not the only woman who cared for you. Continue drinking the coffee and tell me how you feel."

"Yoou are very preetty..."

"Good boy. Now that you feel better, is there anything else I can do for you?"

"I aam afraid to saaay it. You'll kick mee out of yoour house."

She chuckled, "No, I won't. You'll stay here until I verify you are sober enough to leave."

"... I loove the way your booobs crush against meee."

Kate giggled, "Naughty boy. I am trying to make you feel better, and your brain focuses on my body. At least your mood has improved."

When I finished drinking, she leaned back, placed my head on her ample chest, and mumbled, "You can go to sleep now, and when you wake up, you'll be much better."

I recall feeling terrific with my head between her mounds and whispering, "My name is Tommy. And thank you for everything."

I must have fallen asleep. I was dreaming that I was in my own room, and Daisy came inside topless and said seductively, 'Tommy, I thought of leaving you, but I missed feeling your hands kneading my tits.' I didn't hesitate, cupped her breasts that felt bigger than before, and started tweaking them. I woke up hearing a deep laugh. I found my hands massaging Kate's covered mammaries...

I removed my hands and stuttered, "Sorry, I waas dreaming that yoou were Daisy..."

Kate grinned, "I imagined it was the case. Are you a titman?"

"... I like tiits..."

"Will it make you happy if I let you play with mine?"

"Aaare you serious?"

"Tommy, anything to make you feel better."

"Yes, PLEASE..."

Next, Kate slowly unbuttoned her blouse, revealing a silky pink bra. Then she unclasped it, exposing the most gorgeous breasts ever. They were medium size, with large areolas, and very dark, pointy nipples. Seeing them inches from my face took the breath out of me. My lips got dry, and instinctively, I licked them.

She smiled, "That's OK, honey, you can lick them. They are very sensitive."

I was still half drunk, and the unusual situation did not enter my mind. I concentrated on her amazing tits! My tongue met her nipple, and immediately it hardened. I kissed it and followed with milking it lightly. Kate moaned and pulled my head deeper into her breast. My lips stayed latched onto her nipple for a long time. It felt like a pacifier, and I fell asleep again with her nipple between my lips.

I woke up feeling that Kate was moving under me. My mouth was still attached to her beautiful nipple. I disengaged from her boob, feeling less dizzy than before. I asked, "How long was I asleep?"

"Almost 2 hours. It's in the middle of the night now. Luckily, it's Saturday, so neither of us is in a hurry. But I think we should move to my bed."

"I do not have a pajama with me."

"You can sleep in your underwear, and I'll do the same."

I removed my clothes and remained in my briefs. Kate undressed too. She smiled at me and was left topless, saying, "You already saw my breasts, so no need to hide them." On the bottom, she had on an unusual type of boxer shorts.

When the lights went off, I murmured meekly, "Your tits are not just pretty, but very tasty."

Kate laughed, "Is it about my breasts, or you have an oral fixation?"

"Probably both," I admitted.

"You sucked on my tits for hours and they are sore. How about a compromise: We'll spoon when I am behind you. You'll feel my tits pressing on your back, and you'll suck on my thumb."

"We can try it."

Kate moved behind me, pushed her orbs against my bare back, and her nipples poked me. Then her thumb trailed my full lips. I parted them, and she inserted it on top of my tongue. Her thumb was large and felt great. I sucked on it and... fell asleep like a baby soon after.

...

I woke up when the sun's rays hit my eyes. Kate was behind me with her thumb gently teasing my mouth. I milked it lovingly and thought to myself, "This lovely lady knew very little about me, yet she let me into her house, into her bed, suck on her tits... I loved sucking everything of hers!"

We dressed up and ate breakfast. We hardly talked, but our eyes gazed at each other, smiling when they met. After breakfast, Kate notified me she needed to go somewhere. I asked, "Kate, you were so good to me. I don't know how to thank you."

She smiled, "You don't have to. It's OK."

"... I like you very much. May I see you again?..."

"Tommy boy, you owe me nothing."

"That is not the reason. I like you, and I loved having you in my mouth. I slept better than ever before."

Kate joked, "Buy a pacifier and sleep with it."

"It's not the same. Feeling a warm, live body is a totally different experience."

"Tommy dear, you know nothing about me. Better find another Daisy."

"I don't want Daisy. I want you!..."

"On one condition: That you do what I tell you."

I was relieved, "Kate, I'll be happy to obey all your wishes."

She gave me a strange look and blurted, "Be here tonight at 8:30."

...

I was excited beyond belief: Pretty Kate agreed to meet me again at her house! What could be better? Daisy's shadow disappeared like it was never there...

I shaved and dressed nicely. On my way to her house, I stopped to buy a bouquet of red and white carnations. Kate opened the door wearing a long kimono tied at her waist. Despite her tall stature, she looked as feminine as can be with a pretty face and impressive curves.

She thanked me for the colorful flowers and bent her head to kiss my lips. Her smell was intoxicating. I was in love...

She led me to the living room, poured a glass of Chardonnay for us, and said, "Cheers!"

We sipped the drink quietly, watching each other lovingly. Then we moved to the living room and sat on the sofa. As she leaned forward to place a plate with snacks before me, the front of her robe opened and her bare tits spilled out. It didn't seem to bother HER, but my penis jolted, and soon it stiffened, creating a visible tent in my front.

Kate saw it and grinned, "I see you still find my breasts attractive, aren't you?"

"They are magnificent. I still remember how good they feel in my hands, and more importantly, how good they feel in my mouth."

She winked, "Is this a hint you'd like to put them in your mouth again?"

"If you let me, of course."

"Honey, I suggest a compromise: Put your head on my lap, massage my breast with your hand, and I'll let you suck my thumb."

I did as she said and felt like a baby boy being cuddled and cared for by an adopted mother. It was a new and thrilling feeling. I closed my eyes, and enjoyed the experience. Being encouraged to suck her without being shamed for it was empowering. I sucked it hungrily as her soft hand combed my hair.

Then I heard her mumble, "Tommy, your oral craving is impressive. I think my thumb is too small for your mouth. Have you ever thought how it would feel to suck a cock?"

With my eyes still shut, I blabbered around her thumb, "I know Daisy loved giving head. I myself thought about it, but never tried it."

"As an avid oral, aren't you curious why so many women love doing it?"

"... I do... but between fantasizing about it and trying it in real life, there is a big difference. I would never dare ask a man to give him a BJ."

"Do you wish to experience it without shame or embarrassment?"

"Right now, with alcohol on board and playing with your marvelous tits, I feel free and am ready for anything..."

"OK, honey. I'll give you your wish."

I felt her move slightly, remove her thumb from my mouth, and then a soft, warm flesh touched my lips. I was feeling too relaxed to open my eyes. I spread my lips somewhat and kissed the warm thing. Next, it pressed slightly on my lips. I opened them, and the thing began invading my mouth. 'It cannot be', I thought, and gazed at it with half open eyes.

I saw Kate's opened robe with a monster dick advancing into my mouth! I was so surprised that it took me time to react. In the meantime, the big phallus moved deeper into my open mouth. Kate held the back of my head in a way that even if I wanted to retract my head, I wouldn't be able to. But the feeling wasn't bad: Yes, the head was soft and spongy, and the shaft was large, but the push inside was very slow, and the velvety skin felt good.

She stopped once 4" were inside and muttered, "Tommy, get used to it. You'll like it."

Gradually, my initial fear of choking has disappeared, and I started enjoying the large pacifier. It felt veiny yet soft on the outside, and steely hard in the middle. I gingerly milked it and tasted a drop on my tongue. The taste was very mild.

Kate let my mouth adjust to the new foreign body, as her hand caressed my face, and my covered chest. She whispered, "Good boy. Tommy, I love the way your sexy lips engulf my dick, and how your tongue laps on my frenulum."

Her words would have sounded bizarre had I not was under the influence and horny. I told myself that my main goal was to make Kate happy, but deep down, I knew I liked doing it. It was tough to admit it, but her tumescent pecker down my throat felt very good...

Slowly, I began bobbing on her organ, daring to let more of it penetrate my oral cavity. Once about 2" remained outside, I gagged and pulled back slightly. But then I resumed milking her member.

The more I sucked her cock, I felt more confident, and liked it even more. I increased my pace. Suddenly, Kate's body tensed, and she blurted, "Tommy boy, you were awesome, now swallow my juices." Within seconds, her cock began spasming and jet after jet filled my mouth to the rim with warm, slimy, thick liquid. I thought I was choking and attempted to retreat, but Kate's hand kept me from moving back. I held my breath and tried to swallow the fastest I could. Fortunately, just as I thought I was going to drown with her sperm, the stream became a trickle that was more manageable. I finished swallowing everything in my mouth, and then Kate's hand moved from my head. I let her shriveling organ out of my mouth and looked at it again. It was still at half mast, with the helmet being wider than the shaft, and I saw occasional drops coming from the slit. Not thinking too much, I licked the leaky head and milked the remnant seed that was still inside the urethra. I actually liked the taste...

When I was done, I rested my head on her lap and smiled at Kate.

She looked at me lovingly, "Tommy honey, you were wonderful. Thank you. How was it?"

I grinned, "In the beginning, I was too surprised to react or even think about it. But then having your penis in my mouth felt good. I was not prepared to deal with your spunk, but eventually it got better. Geez, Kate, I had no idea you were a shemale..."

She asked quietly, "Are you disappointed?"

"I am astonished more than anything else right now. I know I did not suffer, but the whole idea of having sexual... something with a shemale is too new to have a definitive thought about it."

Kate covered herself with the robe, stood up, smiled at me, and said, "Tommy, go home. When your mind clears up and you know what you want, call me."

I left her house confused. I returned to my room, lay in bed, and thought about the weird experience I just had; I never thought of myself as anything other than heterosexual. I may have been intrigued by cocks, but never imagined I'd ever touch one other than mine. And now I have become a cocksucker, and not of a normal man, but a shemale!... The whole situation was too much to comprehend.

I fell asleep. During the sleep, I had another dream. Kate stood naked in front of me, with her hands on her waist, her tempting tits winking at me, and her giant tool wiggling before my eyes, hypnotizing me like it was a metronome. Kate teased, "Tommy, are you interested, or shall I offer my assets to another boy?" All of a sudden, I realized that having intimate relationship with a person who had both a cock and tits allowed much more fun than either one. I was hooked. I screamed, "Kate, I want you. I want your dick and breasts." She laughed, and slowly her image began fading. I shouted louder, "Please don't go. I love you and want you very much." I woke up soon after.

I tried to think about my dream. My subconscious wanted to continue being with Kate despite her not being 'normal'. The hell; what IS normal these days?!...

My mouth ached to milk her nipples and... suck her cock. Who was I kidding? Having my head on her body with my mouth filled was the ultimate reward!

I called Kate. She didn't answer, and I got her voicemail, "This is Kate. I am unavailable now. Please leave me a message, and I'll get in touch with you as soon as possible."

I said, "Hi Kate. This is Tommy. I thought about it. I'll be happy to spend time with you and put in my mouth everything you let me."