u/Secure_Parfait1313

My first bookstore encounter

Or the deflowering of Erica

When I was in the army I was lonely and a bit horny in a central coast area of California so I decided one Saturday to go to a local adult bookstore for some “spank” material. At the time, I was young and naive. It was my first time ever going to one. As I was walking around the store I notice an older guy watching me. It made me a little nervous being alone so I kept moving away not realizing what he wanted.

As I stopped to look at some magazines I looked over and he had squatted down so only I could see. He had on some loose denim shorts that were extremely short and had pulled them to the side so I could see this huge soft cock he had hidden. It was as big as mine soft (7”) but thicker. I immediately started shaking. I’m still not sure if it was excitement, fear, or nerves but I quickly made a small purchase and walked out back to my car and put the purchases inside.

I looked up and noticed he had followed me outside. Out of nerves I quickly went back inside and used the restroom. I came out to a note on my windshield that said follow me. I looked over and saw the same man, older but handsome smiling. Nervously I nodded yes and smiled.

As I followed him I thought to myself what am I doing and you know what you’re doing at the same time. My dick was semi swollen from excitement during the drive. Even now I shake as I’m writing this.

When we pulled up to his place no words were spoken. I followed him to the door and he gently took my hand and followed him inside. This wasn’t my first time being with another male. When I was in HS I had experimented at sleepovers but no actual sex. This time I was legally a man but this would be more.

He took me to a bedroom with soft sheets on the bed and started kissing me. The first time I had been kissed by a man and when his tongue entered my mouth I thought I would pass out. Thankfully his arms were around me holding me, supporting me, then he started feeling my ass, squeezing it, parting my cheeks and rubbing where he intended. Rubbing my cock through my pants.

The next thing I knew I was on the bed totally naked. He was above me kissing me hands caressing me. His shorts and shirt were off. (How did that happen?) his massive cock agains mine and I was stroking his. Sounds were coming out of me. Soft, moaning, was that me? Then he got a bottle of lube and started prepping me for what was next. Ample amounts of lube on two fingers. Sliding into me, in and out, so wonderful that feeling. Next I raised my legs and I felt his well lubricated tip against my opening pushing.

Pressure at first. Then some pleasure and pain. Not pleasure. Then the pain hit. Oh my god it hurt. He was huge. Larger than anything I could ever have imagined. For what seemed like eternity though he was gentle, patient, in a little further, a little more paint, more pressure, more pleasure, then some movement that eased the pain and increased the pleasure.

In and out. Each downward thrust a little more in. Then I felt him against me. His base against me. His balls tickling me. Him grinding a little as he gave little tiny thrusts. Small kisses as he proudly announced that he was all the way in. That I had taken all of him. Then he started to thrust. Slowly at first. In and out. My eyes locked on his, our bodies moving together. I felt him starting to swell. Then a moment of panic as I remembered we didn’t have protection. Thrusting faster. Pounding me. Familiar smacking sounds but this time it’s against me. Then he suddenly pulls out! Thick liquid warmth on my chest, face, stomach. I’m so turned on!!! Body writhing still!!! Then his mouth takes me all in. Swallowing me whole. Sucking. My balls tighten as I scream out in pure pleasure. He swallows every drop. And as soon as it’s over he caresses me and kisses me. We dress and leave.

For 4 years on and off we meet. Then I moved and never saw him again. I long for him or someone like him. I need to be taken like that again. Loved like that. Used like that again.

I miss it.

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u/Secure_Parfait1313 — 11 days ago

My first sissygasm

I was sitting at work one day and I got a text from a guy I was seeing. Before long it started to get a little steamy.

As the texts went on and on I got extremely turned on. I had started taking some estrogen pills that I got. Not strong but just enough to give me a little effeminate kick.

As we talked my nipples were tingling and I started to get a tremendous ache deep inside like I needed him in me badly. The more he talked the stronger I ached for him and the more desperate I felt.

All of a sudden I had a discharge from my penis. My whole body shuddered and a clear sticky fluid flooded my panties and pants.

Luckily I was seated and wearing dark pants so no one noticed but I sat in this sticky wetness for a few minutes before I realized what it was and was able to go remove my panties

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u/Secure_Parfait1313 — 11 days ago