One of the first experiences that pushed me toward my femboy journey or at least helped me begin accepting the submissive side of myself, was with my ex.
I had told her a few times that I was curious about trying anal and about being fingered. I remember looking away when I said it because even saying it out loud made me feel embarrassed.
She told me she would be okay with doing it.
“Hey, you don’t have to be embarrassed with me. If you want to try it, we can try it. I’m not judging you.”
Hearing that from her made me feel encouraged and a little more comfortable with that side of myself, but I was still too shy to actually ask her to do it. Whenever I thought about asking, I felt awkward and embarrassed.
Sometimes, though, she would press one of her fingers against my asshole or gently massage my taint. It always felt really good, but I still struggled to ask for anything more.
One time, I had a lot going on in my life. I was extremely stressed and nervous, and that day I couldn’t get hard.
It made me feel terrible about myself.
I went down on her and made her orgasm, but even afterward I still couldn’t get fully hard, so eventually we stopped trying.
“I’m sorry.”
“For what?”
“I don’t know. I just feel like I’m disappointing you.”
She kissed me.
“You’re not disappointing me. You don’t have to perform for me.”
“But I can’t even get hard.”
“I don’t care. Come here.”
I felt bad about myself and asked her if we could just cuddle.
“I want to be the little spoon.”
She agreed and wrapped herself around me from behind.
A few minutes into cuddling, everything I had been holding in started to overwhelm me, and I began crying in her arms.
“I’m sorry. I don’t know why I’m crying.”
“You don’t have to apologize.”
“I feel stupid.”
“You’re not stupid. Just stay here.”
She comforted me, kissed me, and kept reassuring me until I slowly calmed down and stopped crying.
We stayed in the same position.
I could feel her hands moving over me as she caressed my chest and neck. A few times, she lightly dragged her fingernails along my hip.
I was tired and still emotional, and without thinking too much about it, I finally brought up what we had talked about before.
“Are you still okay with doing it?”
She said yes, but told me we could talk about it later.
“You need to rest for now.”
I don’t really remember what happened immediately after that because I fell asleep.
The next thing I remember was waking up the following morning.
As I started waking up, she kissed the top of my head.
“Morning, love!”
She said it loudly enough to wake me up properly.
I got out of bed, still naked, and she handed me my underwear and clothes.
I got dressed.
Then she told me to come to her.
I walked over and hugged her.
While I was hugging her, she put her hands underneath my hips.
“Hold onto my neck.”
I wrapped my arms around her neck, and she lifted my legs off the floor.
“You’re actually carrying me?”
She laughed.
“Yes.”
I hid my face against her shoulder because I felt a little embarrassed by how much I liked it.
“Don’t get shy now. Hold on.”
She picked me up and carried me to the bathroom.
I was about 5'10", and she was around 5'11" and athletic, so she could actually do it pretty easily.
When we got to the bathroom, she sat me on the counter.
Then she put toothpaste on my toothbrush and handed it to me.
“Brush your teeth.”
I started brushing.
“Faster. Breakfast is ready.”
Then she left the bathroom.
Something about the whole thing felt really good to me.
Afterward, I climbed down from the bathroom counter, rinsed my mouth, and used the toilet.
Then I went to the table.
She had already made breakfast for us.
We ate a light breakfast together.
After breakfast, she picked me up again and carried me back to our bedroom.
By that point, I felt really clingy and safe around her.
She cuddled me from behind again.
While we were lying there, I finally brought up what I had asked her about the night before.
“I still want you to finger me and massage my prostate.”
She asked, “Are you sure?”
I hesitated for a second and felt my face getting warm.
“Yeah. I’m just nervous.”
“That’s okay. We’ll go slowly. If you want me to stop, tell me.”
“Yes.”
“Then lie down on your back.”
I did what she said.
As soon as I was lying on my back, she started kissing me on the lips.
After a little while, she moved down to my nipple.
I had been very insecure about my chest when I was younger, especially as a kid and teenager, but she loved that part of me.
She started licking my nipple, and I began moaning quietly.
Then I felt her hand against my dick through my pants.
I still wasn’t fully erect.
She kept doing that for a few minutes, then started taking my clothes off. After that, she took hers off too.
Then she took my hand and helped me sit up on the bed.
I barely felt like I had the energy for sex, but I was still enjoying all the attention she was giving me.
She moved behind me and sat back against the headboard.
Then she wrapped her arms around my waist and pulled me backward toward her until I was sitting between her legs with my back resting against her chest. She was basically cuddling me from behind while keeping me close against her.
Then she reached around me.
One hand started rubbing my dick while the other played with my left nipple.
I was making little sounds and whimpering.
Then she told me to lie face down across her lap.
By that point, I felt deep in subspace and extremely receptive to whatever she was doing.
She gently guided me down onto her lap while she stayed sitting and leaning against the headboard.
As soon as I was lying there, I felt two of her fingers against my ass.
At first, she kept both fingers outside. She slowly rubbed around my asshole with them, then alternated between rubbing and gently pressing against it.
“Still okay?”
“Mhm.”
“Use words for me.”
I swallowed.
“Yes. It feels good.”
“Good.”
For a few minutes, I mostly just lay there whimpering from the feeling of her fingers rubbing and pressing against me.
Then I felt something cold and wet against my ass.
It was lube.
She rubbed it around with her index finger, then slowly pushed that finger inside me.
There wasn’t much pain. It went in surprisingly easily.
In a whimpering voice, I said, “Add one more.”
I felt embarrassed almost immediately after saying it and buried my face against the bed.
She laughed softly.
“You asked for it. Don’t hide now.”
“I know.”
“You’re okay.”
She added a second finger.
This time, I moaned louder and felt my dick twitch.
Then I felt her other hand wrap around my dick and start jerking me off while she continued fingering me.
I don’t know exactly how long it took, but I came in her hand fairly quickly.
Afterward, she gently told me to get off her lap and lie down on the bed.
I moved forward off her lap and stayed face down as I settled onto the bed.
Then she went to the bathroom to wash her hand and came back.
By then, I was still lying face down, breathing a little harder and feeling extremely submissive.
I felt her fingers again.
This time, she was behind me and pushed two fingers inside.
I got hard again almost immediately.
She pulled her fingers out.
“Turn around.”
I turned onto my back.
I lifted my legs onto her shoulders, and she put her fingers inside me again.
This time, she curled them.
The feeling was very strange.
From what I had read about the G-spot, I remember thinking that this might be the closest comparison to that kind of sensation.
I moaned much louder.
I think she liked the reaction because, almost immediately afterward, she added another finger.
With the third one, I felt a little pain, but it was mixed with pleasure.
I moaned and came very quickly for the second time.
Afterward, I rolled back onto my stomach.
She lay down over my back and cuddled me from behind, letting her weight rest against me while she kissed near my neck.
I loved the feeling of her weight pressing against my back while I was lying there.
Being underneath her, almost completely covered by her, with so much of our bodies touching, felt incredible to me.
“How do you feel?”
“Are you okay?”
I just made small sounds, like “Mmm.”
“Too much?”
I shook my head.
“Good. You don’t have to talk yet. Just stay still.”
I felt strange, but not in a bad way.
I was actually very happy.
More than anything, I just wanted to be hers.
I think we stayed like that for around ten or fifteen minutes.
Eventually, I started feeling like I needed to pee, so I told her.
She moved off my back and lay down to my left while I went to the bathroom.
When I came back into the room, she was already underneath the blanket.
She lifted it and looked at me.
“Come here, baby.”
I climbed into bed with her.
I tried to be the big spoon.
“No.”
“No?”
“Come here. You’re the little spoon.”
I felt myself getting shy again, but I turned around anyway.
“There you go.”
I felt extremely needy.
I shifted backward until I was as close to her as I could get.
She moved closer too, wrapped one arm around my waist, and pulled me even closer to herself.
I told her I loved it.
The whole thing felt euphoric.
She told me we needed to buy a strap-on for next time.
I just answered, “Mmm.”
After a little while, I suddenly realized that I hadn’t really done anything for her that morning.
I turned around so we were cuddling face-to-face.
“I haven’t really done anything for you.”
“You don’t have to keep score.”
“I still want to.”
She smiled.
“Then ask me what you want.”
I felt a little sheepish when I asked, “Can I suck your nipples?”
“Yes, baby.”
I started sucking her nipples.
Almost immediately, she started making noises.
That surprised me because she usually didn’t react that strongly that early.
Then I asked if I could go down on her.
“Yes, baby.”
I moved lower and started licking her.
I had never seen her that wet during sex before.
I asked her, “Are you really aroused?”
“Very.”
“Do you want me to finger you?”
“Yes.”
As usual, I slipped two fingers inside her.
Almost immediately, she said, “No, make it three.”
So I added another finger.
This time, everything felt different.
While I was fingering her and eating her out, I could hear the wet sounds of my fingers moving inside her.
After a few minutes, she put one hand on top of my head and gathered some of my long hair in her hand.
She gently pulled me upward and brought me up to kiss her.
After we kissed, she told me, “Lie down.”
I lay down on my back.
She got up and sat on my face.
Then she told me to eat her out.
I couldn’t reach her clitoris very well from that position, so I focused lower, using my tongue as deeply as I could while she touched herself with one hand and jerked me off with the other.
After a few minutes, I heard her moans getting louder and louder.
Then I felt her thighs tighten around my head and felt her body quiver above me.
It became harder for me to breathe.
A moment later, I felt a small amount of warm fluid on my face.
I found it extremely hot.
At the same time, she was squeezing my dick harder without really seeming to notice she was doing it.
Eventually, she relaxed her legs a little and stayed still for a moment.
Then she lifted herself off my face.
“You okay?”
“Yes.”
“Too much?”
“No.”
She touched my face.
“Tell me if it ever is.”
“Okay.”
“Do you want to cum?”
“Please.”
She moved on top of me and lowered herself onto my dick.
Then she bent forward.
While she moved on top of me, she also started licking my nipples.
I came inside her within a few minutes.
Afterward, she cuddled me for another two or three minutes.
I figured the amount of cum and fluid, combined with how long we had been having sex, might have felt like a lot for her too.
I asked her, “Can I pick you up and take you to the shower so we can just wash ourselves?”
She said yes.
I picked her up and carried her to the shower.
She washed my face first and kissed me.
Then she gently pushed me forward.
“Bend a little.”
I did.
She ran the warm water over my ass.
Everything there felt very sensitive and a little sore after what we had done. The warm water made the sensitivity stronger, and I still had that strange, lingering submissive feeling from everything that had happened.
“Aww.”
She laughed.
“Sensitive?”
“Very.”
“Poor baby.”
I felt embarrassed by how much I liked hearing her say that.
Then I washed her too.
Afterward, I realized we only had her towel with us.
I gave it to her.
She started drying herself, and when she tried to dry me too, I protested.
“Nooo. That’s your towel.”
She gave me a look.
“I squirted on your face. You came inside me. It’s okay to use my towel on you.”
She dried me anyway.
Then she hugged me again.
“Lift your legs.”
I did.
This time, after I lifted them, instead of putting both hands under my hips like she had before, she supported me mostly with one arm while keeping me held tightly against her. Her hand was between my legs, pressed against my asshole as she held me.
There was something about being held like that, especially after everything we had just done, that made the position feel even more sexual and submissive to me.
Then she carried me back to bed.
She put me down on the bed, walked around to the other side, and climbed in beside me.
Then she pulled me into the little-spoon position again.
She talked to me softly, cuddled me, kissed me, and kept taking care of me.
“You okay now?”
“Mhm.”
“Still feeling shy about any of it?”
“A little.”
She kissed the back of my head.
“You don’t have to be shy with me.”
I relaxed a little more against her.
I don’t know how long we stayed like that.
Eventually, I fell asleep.
