Gay Fem Boy Finds His Man

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was wonderful. We've finally mated and I'm seeded and fertilized and had a special orgasm to boot! I had a climax better I have ever imagined possible. I even started giggling as spasms of pleasure coursed through my body!

He continued to kiss me as he told me how much he loves me as he rocked gently in and out of my wet and gushy hole until be began to soften.

We rolled on our sides and he made remained in me for as long as he could.

I rolled over on my stomach and faced him, hoping I only oozed a tiny little mess. He rubbed my butt gently with his hand.

Teasingly he asked me, "Are we going to have a baby?" he asked in his kindest voice.

"I hope so, honey." I replied in the most sweet and feminine voice I could muster.

"Good girl. It could happen, you know. I want my sperm in you all the time." he replied with loving finality.

"I love that idea."

"How about I give you a little kiss." he said as he got upright and lay between my legs.

I spread my legs to make room for him, and he began licking my hole. I was a wonderful act of love, and was a most calming and sexual experience ever. I'd been worrying about my hole after this experience, but now in my mind, all was well and good!

I felt wonderful. When he was done, we took a nap.

After a bit, it was time to get up and dress for hor d' oeurves tonight with other guests. As I began to think about dressing for the occasion, Robert came up to me and gave me a big hug and a kiss.

I was so lost in the moment during his sudden embrace, I neglected to intercept a little rivulet of semen that escaped and slowly made it's way down my leg, tickling every inch of the way. It felt very sexy!

"Oops. I should take a shower." I said, noticing my dribble.

"No, you're just fine. I think it's cute that you had a little dribble."

"But I smell like sex, too." I answered.

"I know. I like it. I'm proud of you, Honey."

And that was that, so I began to lay out my clothes for the community happy hour.

I decided to wear my black, below the belly leggings and a my black panty thongs. The leggings are nice and tight but ride fairly low. For a top I put on a thin white fluffy blouse with a mini cami under it, giving me some modesty in case I take off my spa jacket. I plan to wear it unzipped so I can show some jiggle under my blouse. I combed my hair back and held it with a rainbow scrunchie, then slipped into my pink flip flops with plastic flowers so I could show my pretty toes.

I lightly retouched my make up and realized how happy I felt being able to dress for Robert, especially knowing Robert's seed was inside me.

We joined the people milling about sampling hors d' oeuvres and wine.

As we stood around and made chit chat, I noticed that the more manly partners seemed to wander away and separate from us less manly partners. Robert gave me a nudge, so I stayed with "my" group.

This separation I learned was the custom here and soon we eight guys were all in a gaggle. One guy started acting out and talking with a very gay and girly inflection. After a couple of glasses of wine, we were all doing it and making feminine gestures and carrying on. We were soon all hinting about sexual things our partners liked, and how much we loved to do this and that.

I was the only one dressed this fem, but the guys appreciated that and remarked positively about what I was wearing. We all made little jokes and some shared that they often wore feminine things underneath, or to parties and, of course to bed.

We all got to giggling stupidly as we kept our wine glasses full. It was really fun being one of them and for the first time in my life, enjoying "coming out" into a different sexual identity. I really did feel like a blushing bride!

With more wine we began to get more silly, all of us at least hinting that we just came from an afternoon of having powerful sex with our alpha males!

After my second glass of wine, I noticed Robert looking in my direction. That meant it was time for me to leave my new friends. As I left the gaggle, I couldn't help but notice "My" group did act like a bunch of silly girls! I smiled proudly to myself.

We went to the restaurant and had two nice steaks and more wine. I felt completely different. I felt comfortable dressed the way I was, I enjoyed being with the other "boys" tonight, and I feel really great that I've crossed the Rubicon and am carrying Robert's seed. I felt happy, loved, and complete.

But, I was about done in and ready to go back to the room.

We got back to the room and poured a glass of wine.

"I'm beat. I can't wait to get to bed." I said.

"Me too."

We went in the bathroom and maneuvered around each other until he got done and left. I lubed my tender hole again just in case and put on my sheer baby doll nighty with the frilly panties and got into bed with Robert, who was nude.

I snuggled up to him and gave him a kiss, then turned my back to him to spoon with him. He put his arm over me to comfort me, then moved it under my nighty and gently rubbed my breasts and nipples before coming to rest on my stomach.

"That's my sweetieboy. Do you feel OK, honey?" he asked me, kissing my neck.

"Will it always hurt?" I asked.

"Not really. After this vacation, you should be used to it. The more we do it, the easier it becomes. Are you hurting?"

"It hurt at first, but it's not bad now."

"It a matter of me being careful, and you getting used to it."

"How do you know that?" I asked, too quickly.

"Google, honey."

"I think I'm looking forward to that." I said, careful to not give the wrong impression.

He reached under my nighty and began playing with my nipples again. I could feel him poking me with his cock, so I reached back and lowered my panties and kicked them off. Then I put his cock up to my lubed hole. I was hoping we could do it again! Get that baby in shape!

With very little discomfort, he was balls deep inside me.

He pulled out and rolled me over and lifted me so I would be on my knees. I widened my legs, pushing back to present my boy pussy to him as he painlessly reentered me. He began working in and out, holding my hips to him, as I enjoyed each thrust.

"Oh, honey. You are wonderful. You make me feel so good. I love you." he whispered to me.

I was fascinated my the slapping of his butt and balls on me as he grasped my hips and pounded deeply in me.

I squeezed my pussy tightly as my skin began to tingle and my cock began twitching and oozing as he plunged in and out of me. He grunted and I felt him twitching gently as he gave me another measure of his feminizing liquid for me to absorb.

We gradually sunk into the bed with Robert on top of me.

In a few minutes of gentle kisses, he rolled off of me and kissed me gently.

"That was wonderful. Good night, honey." he said.

"Good night, sweetie." I replied.

I was thinking, "Wow. My first quickie!"

We quickly dozed off after that. I was beat. But, boy howdy, the dreams I had.

Chapter Seven

I woke up early and did my thing. There was no semen that I could see in the toilet so happily it all soaked in and I didn't jettison any of Robert's sperm. I went ahead and did a douche and shot a bit of silicone lube up me. I took a shower and felt around a little back there. I was only slightly sore but I was definitely looser down there than before. Other than that I was I was pleased to find myself in a very happy mood.

There wasn't much to do in Guerneville, so we had a leisurely breakfast at a local bar/restaurant. I really had a case of the grins. I don't know what got into me, but I felt as if I was the happiest person in the world. I couldn't help but wonder, "What is in that stuff besides sperm? Tranquilizers?"

Finally, we each got the same idea and decided to head back to the resort. Robert decided to call to have the room made up so we could go to the pool again and not get in the way of housekeeping. Since I got a bit of sunburn on my nipples yesterday, this time I had little choice but to wear my top, and accept my tan lines as being part of who I am.

As we began undressing we took our time and when we were both naked, he gathered me up in his arms and maneuvered me onto a sitting position on the bed.

"Did you think I forgot about my sweetieboy?" he said as he moved my legs out of the way and knelt down on the carpet and began to kiss and lick my little cock.

He slowly licked along the side and the bottom and around the head, then licked all around my crotch. I began to breathe heavily as he took my cock in his mouth. He slowly sucked on me and massaged all around the head with this tongue, causing me to feel as if I was getting tickled by a thousand butterflies as I crept close to a climax. As I writhed with passion, he knowingly licked the head as if it were a clitoris until I had the most wonderful slow motion climax imaginable, as my thin semen dribbled into this mouth.

"Oh, baby. That was wonderful." I said, breathlessly.

"Hummm.... I love you, honey." he replied.

I climbed back on the bed and rested for a bit waiting for the tingling of my orgasm to subside while he softly rubbed my sides and my stomach.

We kissed deeply for a few moments, and then he scooted down between my legs. He lubed up his cock and wiped some on my hole and pushed my legs up. I widened my legs more and reached down to guide him to my opening.

"Careful, baby, she's still a little tender down there.".

"I'll be gentle, my love." he replied.

I was in worried disbelief that he went in so easy with just a few gentle thrusts, and almost no pain. I felt his heavy balls bouncing off my buttocks, as he began to work himself in and out slowly and purposefully.

As he began to pick up the pace of his thrusts, he lay fully down on top of me. We began kissing as I got my hips in motion to match his thrusts and held him tightly, buffeted by his earnest pounding. I squeezed as tightly as I could in time to his thrusts in the hope of achieving a climax. The harder I squeezed the better it felt and the closer I came.

As I worked my hips and my tired sphincter began to slacken, I strived to hurry my climax by pleading in his ear. Since we have been having a lot of sex lately, our sessions have become longer and less frantic until right at the end when he really goes for it. If I climax, that's when it happens.

"Oh, baby. I am so close!"

He started thrusting more powerfully, and I held on tightly as I changed my angle a bit, greedy for my pleasure! My little cock oozed and quivered gently in sync with the slow rolling waves of pleasure sweeping over me as Robert thrust expertly to bring me to my special climax, realizing now that my orgasm was born of a different process than his.

"Arrrgh!" came out of his mouth as he began pulsing inside me just as my climax came and waves of pleasure wracked through my body. I held him tightly, feeling every twitch of his cock as I tingled from every pore and nerve ending in my body as if each had it's own personal climax.

He rested on top of me thrusting gently as I greedily took every iota of pleasure I could. When we regained our composure and rolled over, I felt loose, wet, and messy, and very loved as I rolled face down to keep from leaking.

"How are feeling, honey." he asked.

"Absolutely wonderful." I replied.

"Ready to go to the pool?" he asked as he gently rubbed my butt.

"Sure, in a bit." I lied. I was still foggy headed and buzzing from my climax.

After we rested a bit, we put on our suits and headed for the pool. The shady chairs were taken, so I had to take the sun until it moved.

I smiled and nodded to guys I met the other night when we "boys" all got together for a giggle. We all had secrets to share.

After two hours, it was time to go in. I was getting cooked!

We went back to the room and I took off my clothes and we took a nice cool shower together. Robert was getting frisky again, and I was wondering if maybe I could give him head and give my boy pussy a break.

We got out of the shower and the first thing out of my mouth, was "Oh, wow!". I had a serious and obvious top and bottom tan line, if you consider darkened freckles a tan. I didn't know how to feel about that, except that it was obvious I have been wearing a two piece womans bathing suit. Oh well.

We both lay on the cool sheets, naked and spent.

We went to dinner in a nice up scale restruant, then went back to the resort and began packing and went to bed. I missed getting the dick. I know he probably thinks I don't want it all the time, but I do. And besides that, his semen seems like a drug. Really. I feel better than I have ever felt and different in a positive way.

We woke up early, and I got in the shower and douched and lubed. I got my travel mirror and positioned it so I could look at my boy pussy. It looked like a coin slot. It was not a round, tight little sphincter anymore. Not that it matters, I guess. All in all, it's fair to say, I've changed.

So I slipped back into bed. Robert was stirring, and gave me several sweet "morning breath" kisses which I gladly accepted.

And with that, he began kissing me again, and for the first time in my life I mouthed the words:

"Please fuck me, honey!"

It seems so dirty and unlike me, but today and the last few days have been really special!

I turned my back to him and put his rigid cock up against my hole and pushed toward him. He was inside me in a second.

He rolled me face down, and began pounding his cock into me.

"Let's turn around, honey." he said as he withdrew and rolled my on my back.

He pushed my legs up all they way to where I could rest them on his shoulders and entered me again. I pushed my hips up to help him go as deeply as possible, as he put his arms outside my legs pinning me, allowing my boy pussy to be pummeled.

I began to cry out in my most uninhibited and feminine of voices, and egged him on by panting and huffing like a dime store harlot.

"Oh baby, please." I cried as the tingling began to take over and I began to come close to my orgasm.

"That's my girl. Daddy knows you what you need." he said as he pounded into me, constantly changing positions so as to hit the places inside me that got me over the edge.

"Oh, baby!" I cried out, seconds away from my orgasm.

"Oh!" I almost screamed as my orgasm washed over me with a the force of a Tsunami!

"Oh honey, that's a good girl, let it come." he said as he kept on thrusting into me. I clamped my arms and legs around him so tightly, we became one. He finally let out a roar for all to hear as I felt his familiar pulsing as he released another flood of his feminizing potion deep within me.

"Oh, honey. That was really special." he replied.

"That was wonderful." I said as I rolled over to let his juice soak in.

He began rubbing my butt again, then moved down to play with my little balls and asked me,

"Do you really need to keep these, honey? The hormones would work better." he said.

I replied, "I should probably keep them for now, honey. I don't know if there is much demand for a story about that!"

And after that, we checked out and on the drive back to the hotel we began to talk seriously about matrimony, and agreed to come back again as soon as we had time.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymousabout 2 years ago

very nice romantic story. I get sick of all the stories that are all about cock and no kissing or romance. Thank you. Great job.

jamie427jamie427about 2 years ago

Absolutely loved this, so perfect!

AnonymousAnonymousover 3 years ago
Pregnant

Hey! I am a mtf crossdresser from india. I loved reading your story.. Esp the section you would like to get pregnant. Any cd with a true feminine heart desire to have a baby..

AnonymousAnonymousabout 4 years ago
Get pregnant

Absolutely loving this story...I always fantasise to bear children of my man, breastfeed them....do my duty as a “wife” of my man....yes please. Would love you to get feminised and uterus and bear children

Happyman47Happyman47over 5 years ago
Great story

I loved your story but you should have described yourself at the beginning. I got lost a few times. Are you a guy who is a cross dresser and wears girls cloths under your male cloths?

Show More
Share this Story

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Pink Fuzzy Slippers A guy falls in love and becomes a man's wife.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
More Stories