Posted in Story: Fiction, English | Categories: Fetish, First Time, Taboo, Lesbian Sex, Romance, Toys and Masturbation | Tags: masturbation, lesbian, toys, straight, Shemale, Trans
After swallowing my load, Joy wiggled her way up my body. She laid on top of me with her face next to mine, looking down into the pillow as I held her tight little naked body. I could feel her mound on my now-softening cock and our breasts were pressed together. I held her butt, cupping both cheeks. She was silent for several minutes, then raised her head and whispered in my ear:
"Is there something you want to tell me?"
I said stared at the ceiling and said nothing.
"Don't you think you owe me an explanation? That I deserve one?"
After a minute of piercing silence I replied, "It's not what you think, I'm not a guy... I'm not a ladyboy or transgender..."
And then it all came out, my whole sordid, awkward story. Joy became the first person I ever told. As I explained, I cried but I felt like the burden had finally been lifted. She became the first besides my family that knew my secret. She had a few questions and I answered them honestly. She cried too. Then we lay there silently for several minutes until I broke it.
"Huh? What do you mean 'now what'?" She sounded hurt and a little irritated. Then continued, "I love you, Maricel".
Ane we fell back into silence for who knows how long. The first one to come back to life was Junior. He began stirring underneath her pussy. The little prick was getting hard again! Joy lifted her face and kissed me. We began making out with passion, Joy grinding on my cock as we kissed. As Joy moved forward for me to suck her nipples, I stabbed her with my dick and it slid inside her. She backed up and took it all, although there wasn't much to take. It was sort of awkward, being so small there wasn't a lot of room for thrusting. Joy figured out a solution, she began to grind her clit on my pubic bone by moving her hips in a circular motion. We fucked like that in a frenzy and she came with me inside her. It felt awesome when her pussy contracted and spasmed, I never experienced that before. The second one put me over the edge, and we orgasmed together. Mine was dry, but wow... it felt great! The word "earthshaking"came to mind. Then I realized I had hold of one of her titties with a death grip. I released it and she rolled off me and to my side.
Weeks passed, and Joy and I were happy and as sexually-active as newlyweds. But something began bugging me over time. I realized that Joy needed a man... and I realized that I needed a cock. When we made love, things were fine. But when we fucking GOT IT ON... we both needed a guy. My problem was when and how to broach the subject with Joy. She was conservative, and introducing another party into our sex life might make her uncomfortable, or worse, hurt.
I finally raised he question one night after we had a great fuck in the shower. We had just prepped and climbed into bed.
"Do you ever miss fucking guys?"
"Why, do you?"
"I asked you first...."
"Honestly? Yes. Do you?"
And it was that simple! Then we began to discuss the logistics, who and when, etc. It would take some thinking and some careful planning. Joy had no experience with picking up strangers. I had plenty of experience, but I kind of dreaded seeing her with a man. The idea was hot, but felt kind of threatening. And where would we find someone? After all, we were a couple and deeply in love. It wouldn't be so easy to let a stranger in on our love life. It's the most intimate thing we shared together! Getting someone we knew and mutually admired wouldn't be simple either. What if something went wrong, and we still had to see that person? What would it do to the friendship? Wouldn't it be awkward?
Joy fell asleep, she had to work in the morning but I was off. I lay there thinking and came up with an idea. The next morning, as soon as she left, I showered and headed to Makati. There was a sex shop there that I had heard about. As much experience as I had, I never ventured into toys at all so this was another first for me. I was astounded when I walked through the door. First, the very strong smell of plastic. latex and silicone hit me. Next, I was amazed by the selection! I browsed the aisles, looking at the many, many toys. I wondered what some of them were; how they would be used and what it would feel like. I browsed the vibrators and dildos next, then came to the section I was looking for... strap-ons. I was feeling so fucking horny by now, I leaked some cum into my panty.
All of the ones I liked were so expensive! But I continued looking, the selection was immense. Finally, I found what looked like a pretty good one; large, flexible, an internal vibrator, and a comfortable-looking harness. I felt it... it had natural feeling skin. Mmmm... my knees shook a little as I squeezed it. This is it! I just barely had enough money to buy it and get home. I walked to the counter.
Suddenly I was embarrassed, but the clerk, a middle-aged man, rang it up like it was a bag of chips or something.
"You have batteries?"
"Well, you're gonna need some". He reached for the batteries and rang them up.
"LUBE!" He rolled his eyes at me.
"Yeah, give me some...." I didn't know if we needed it or not! I imagined she would be pretty wet. Shit... even without a pussy, I was wet from just looking at this thing.
"Yes, of course"
He rang everything up and I had just enough to pay for it all with nothing left over. Looks like I'd be walking back to Taguig. I guess I could cut across the golf course. I paid him and exited the store. As soon as I got outside, a sleazy-looking guy hit on me. "Ugh", I thought.
But then I had an idea. I told him I would wank him for enough money to take the jeep home. He was looking for more than a hand-job, but he took me up on it as he was horny and the price was right. My memory bank was going wild as we walked into the alley. I wondered if this was cheating? I took the cash, kissed the creep and let him feel my tits as I unzipped his pants. He became hard quickly and I began stroking him. He pleaded for a blowjob but I told him no. He decided to take what he could get and finally quit pawing at me and relaxed against the building. I stood so as to block the view from the street and tugged his average-sized dick. I started talking dirty; telling him how much I loved his hard fucking huge cock. OK, I lied but that's business. In just a few minutes, he blew his load onto my hand and arm. I was a little turned on, but mostly I just felt slutty. Then I remembered the cause... I would give Joy the surprise of her life this evening. I wiped the cum off my arm and left the alley. The man gave me a tip, so I had enough for lunch. Bonus! I got home a few hours before Joy.
I bathed again, I felt so dirty. It felt good to make sure there was no "evidence" left on me, and it cleansed my feeling about what I had done. I installed the batteries and naked, I donned the dildo and fitted the harness, adjusting as necessary. It rode overtop my own little cock, I pulled it straight up and put the dildo over it. Since the toy was flexible, I folded it downward and put on a pair of black unisex briefs that I had. Then I dressed adrogynously, and tucked my hair into a backwards ball cap. I felt ready.
Right on time, Joy arrived. I heard the key in the lock and I was standing there, ready with "my package". My little cock was half-hard behind the big one. When she walked through the door, I stepped out from behind it, whirled her around, and kissed her. She dropped her backpack on the floor and I kicked the door shut, scooped her up in my arms and laid her on the bed. While kissing her lips, neck and ears, I unbuttoned her uniform blouse, opened it up, and reached under her and unsnapped her bra. I pulled it up over her shoulders then resumed kissing her while I unzipped her skirt. She was stunned, but of course offered no resistance. The skirt gone, I wasted no time stripping off her panty and I dropped to my knees on the floor between her legs. I placed her legs over my shoulders and ate her pussy and butt like never before! She was soaked and wiggling so much it was hard to keep my face in her crotch. She smelled great after a full shift at work, and tasted fantastic! I continued to lick her through two orgasms, and swallowed as much as I could. Then I stood and unzipped my jeans, and pulled down my jeans just enough to expose the monster.
Her eyes were glued to it now as I bent it upwards into "action position" and stroked it like a real cock. Her eyes widened. Just for safe measure, I reached into my back pocket with one hand and extracted the tube of gel, and rubbed it all over the fake dick in front of her. Then I gently lifted her legs, placed her feet on my shoulders and rubbed the head of the dildo in her wet, slippery slit. She closed her eyes and I began to push.
Joy had never been penetrated with something of this size. I was careful and went slowly. I was glad I bought the lube, even if I had to wank that pervert afterwards. I pushed in, she was breathing in short gasps and doing her best to take it. Finally, I was all the way in. My real cock was now fully erect behind the fake one as I fucked my girl slowly, in and out. Joy was moaning now, no more pain. And I fucked her like she had never been fucked before. Her eyes rolled back in her head as I wore her little pussy out. When we got to the point where she couldn't take anymore... I reached down and pressed the switch! The vibrator kicked on full force.
"Ohhh MYYY... SHETT!!!" Joy was beside herself, now starting to kick her legs. I held them still and continued fucking. The whirrrr of the vibrator raised and lowered in pitch to my stroking as the fake dick went in and out of her hot, tight pussyhole. She grippe... Read More