How I Started Craving Cock

During my college graduate program, I met a female classmate who became a FWB. I was a small town guy and only knew about sex play with women in a more "traditional" manner. I did not realize at the time that she was way more adventurous and way more experienced than I was.

I grew up in a small rural town. So when I saw a dildo on her nightstand by her bed, I asked about it. I tried to just seem curious and I asked what things would you be doing with that even though I knew - or I thought I knew. Of course I thought she used it on herself when she jilled-off. Her response was "James uses it on me when he stops by." I thought that would be fun to use it on her. I didn't think anything about her with James since I knew she was busy with others besides me. Then she looked at me and said, "and then I use it on him."

That got my attention and I think she was gauging my reaction. I know I had a little surprised look - I'm sure my eyebrows gave it way - but all I said was "that's interesting." And then we started with our standard, routine play and we both needed to do.

The next time we got together the dildo was still on her nightstand along with a tube of KY jelly. We crawled into her bed and started playing with each other with our tongues and fingers. She was pulling on my cock when I felt her finger circle my butt hole. I know I was breathing different once she started probing but I didn't stop her or say anything. And after a short period, I could feel her finger tip wiggling inside me. I think my cock spasmed a little and got harder.

I think she saw me close my eyes and let out a big breath. My cock head was a little wet at the tip when she whispered in my ear, "feels good doesn't it?". I moaned back, "oh yes. Yes it does". She took my cock head into her hot, wet mouth. i could only mosn as i felt her wet tongue slide apund my cum slit. Then she reached over to the nightstand and picked up the KY jelly. She put a little on her finger that had been inside me and then started to coat my little hole with the jelly. It felt cold at first but it made it easier for her to put her finger deeper in my ass.

When she started massaging my hole open, I heard myself releasing a little moan. I reached down to my cock and started to jack. But she quickly took my hand away and said "Just wait. I can see that you like it. I promise you it will be a wonderful experience."

She started with one finger and I could feel when started with two fingers. And then I could feel her working the third finger in to me. With each additional finger my hole became more relaxed and I started to crave her fingers in me deeper. I didn't touch myself but I could feel cum running down from the tip of my cock. I was on my back and she gently moved my knees up by my chest to give her better access to my butt hole.

When she stopped I released a big breath and she said, "it's gonna get better. Just don't open your eyes and relax." So I did as she directed. Then I could feel the head of her dildo pushing at the entrance of my hole.

She continued slowly working it into me while whispering to me, "I thought you would like it. See how it feels when I rub it around the entrance of your opening and put just the head inside of you. That's how I like it when James uses it on my ass when we start. That's how James likes to start too. "

I nodded my head and said "yes I can see why you like it."

" I thought you would like it. Haven't you ever touched your boy pussy before? Haven't you ever just rubbed around your pussy opening?"

I didn't respond because I didn't want to tell her the truth that I when I was in middle school I did touch my boy pussy and that I wondered how a cock would feel using hole. It was usual for me to include playing with my ass opening. I even started using my mothers douching nozzle to gently probe my private hole. I was breathing deep and relaxing into the feeling, a feeling I had been missing for some time.

She continue to push the dildo in me and opened my hole for the entire dildo. I could feel the stream of pre-cum running down my cock. And I could tell she was working at something inside me that was building the feeling of cumming. Still, I didn't touch myself like she ordered.

"James likes me to call his little hole his sissy pussy. Would you like that too? Do you want me to continue fucking your little sissy pussy?"

"Yes please I gently moaned. Don't stop."

"Don't stop what? What do you need Joe?" She said as she slowed down rubbing my hole with here dildo. Then she took my hard cock at the base and squeezed so that it kept me from squirting my cum. "You need to be very specific on what you me to do and don't whisper. Say it louder and clearly."

"Please keep fucking my sissy pussy. Please don't stop." I said in my usual voice. Even I could hear the desire and need in my voice

"I'm not going to stop honey. I enjoy hearing you moan like a little sissy and beg for my cock dildo. Do you enjoy this size cock or do you want a bigger, fatter dildo working your hole open."

"Bigger please. Fatter, please. Please use my hole and open it wide. Make me gape."

"My, my, my, little Joe wants a gaping sissy pussy doesn't he?" Her voice seemed louder and it raised my awareness of what was happening. I wasn't in a dream state, this was really happening. I was getting fucked by my friend with her dildo that's been in her cunt, her ass, her friend James ass. I was letting all my secret nasty fantasies out in front of her.

"Yes, I want my sissy pussy to gape and be able to take any cock you want me to take". I could feel the urge building to cum but she grip at its base was keeping me from erupting.

"Any cock? Do you want to feel James cock cum in your sissy pussy?"

"GOD YES! GIVE MY SISSU PUSSY TO YOUR FRIENDS"

I took a deep breath in as my hips pushed forward. She relaxed her grip on my bock and I released a big stream of come all over my chest, belly and on my face. My cock was pulsing streams of jizz as my balls emptied.

"I think that's a big yes" she said with a little laugh. She had left the dildo in me and milked the last bit of come from my cock. I kept my eyes closed because I was very relaxed and was just trying to catch my breath. I could feel her fingers gathering the cum on my chest and stomach. Then I felt her fingers rubbing along my lips and encouraging me to open my mouth to her fingertips. I could smell my seed and feel its wetness on my lips.

"Here honey, I've tasted it. It's not bad. In fact I really like how your seed tastes since you don't smoke. I think you'll like it."

I opened my mouth and felt her cum covered fingers enter. I closed my mouth around her fingers and started sucking and licking her fingers clean.

"You did that very well Joe. I think our play times are gonna be more fun now. But I get this feeling you're not completely new to this. I bet your wife doesn't play like this at all. But that's OK I'm not gonna tell her. I want these type play sessions for myself."

"I'm going to leave that cock in you as you recover from your spraying baby seed all over your self. James always gets harder quicker if i leave it in his sissy pussy".

I left my eyes closed so I couldn't look her in the eyes. I wasn't sure i was comfortable exposing my enjoyment of getting my ass pussy used by my friends dildo. And what did it mean that admitting that I wanted her friend James fucking my sissy pussy.

"Yes" she said, "I think we're both going to enjoy our play sessions even more now.". I just whispered my confession "yes I will."