For some backstory on this particular tale click here.
I should have known better than to pick up a stranger on the side of the road but, had you seen her, you'd have done the same. Even driving past her on the on-ramp as I sped up to get onto the freeway I could tell she was a looker. In that split second I decided to stop my car and back down the side of the road where she was standing, helpless, next to her vehicle.
"Oh, thank you so much!" she said as I got out of my car. I had checked her out in my rear view mirror to see if I had been correct in my quick assessment. Indeed, she was a nubile young woman with big boobs, a small waist, and very pretty face. I looked at her in that order. She was wearing a faux fur coat with a skirt and low cut shirt underneath.
She told me the sad story about her car breaking down on her way home from work and blah, blah, blah. I'm sure she said a lot but my eyes were locked on her bountiful breasts. I'm usually able to keep my eyes north of a woman's bustline but this girl, Callie, might as well have been wearing a big arrow in front of her face pointing to her cleavage.
Knowing nothing about cars, I volunteered to drive her home. "That's great," she said, "I need to get home before Bobby does."
Bobby? Oh, shit. It wasn't like I had any chance of sleeping with this girl but it's always such a nutcrusher to learn that the hot chick you're talking to has a boyfriend. I had already made the offer and couldn't rescind it. It'd still be nice looking at Callie on the way to her place. I'm never one to refuse some eye candy.
She had only been a couple mile away from home when she broke down. I wondered where she had been working to be "leaving work" so early in the morning and she answered my question when she told me about her job at the Velvet Touch massage parlor. Mentioning how much I enjoyed a good massage she offered to hook me up with one once I got her home.
She lived in a little trailer far off the side of a two lane blacktop. The ruts leading up to the patch where she had me park were nearly enough to bottom out my car. I was amazed that such a put-together girl could live in such apparent squalor.
The inside of the trailer bespoke a different story. It was immaculate, not the shithole I expected from the rusted through trim and the cinder blocks used for a variety of purposes.
I didn't think she could look any better than she had but Callie took off her faux fur coat, revealing just how shapely her figure really was. "Now, how about that massage?" she asked. I swear, you could almost hear the "bom chicka-wah-wah" of the porn music starting up as soon as she said it.
She showed me to her front bedroom where she had a massage table set up. After allowing me some privacy to undress (not that I would have minded otherwise), she lit some candles, started a CD of meditative music, and spread some oil on her palms that she warmed with the heat of her body.
Her fingers were a revelation. She worked my muscles with a skill I'd never known before. It hurt, but in a good way. It wasn't just my back that she worked on, either. She gave special attention to my calves where she worked out quite a few knots. She seemed to electrify every inch of my body.
She hummed along with the music, occasionally talking to me, telling me more about her life. Despite being lulled into a state of extreme relaxation, her fingers and voice kept me aroused, so much so that I was tenting my towel when she had me roll over to massage me from the front.
She looked from the bulge under my towel to my face and smiled. She went to work on my shoulders and chest, down to my feet, and back up my legs to my thighs and finally she took ahold of my cock.
Putting more oil on her palms, she slid them over my turgid dick. Her hands were strong and sure. She began stroking me, smiling. "You have a lot of stress built up in your chakras," she said. "I'm going to help you release it."
With that, she stripped out of her clothes revealing a body that looked even better naked than clothed. She held her hand in front of her face and licked her fingers before putting them between her legs and wetting her pussy. This display did the impossible; it made me even harder for her.
She climbed up onto me, her knees on the edge of the massage table on either side of me. She took my oil-slicked cock and slowly slid it inside of her as she lowered herself onto me. She felt wonderful and that only made what happened next even more shocking.
"What the fuck is going on here?" came a gruff voice.
Callie turned, still on top of me, and exclaimed, "Bobby! It's not not what it looks like!"
"Callie, for Christ's sake. How could it not be what it looks like?" came the voice. I couldn't see the person yelling as Callie was between me and them but I noticed that the voice wasn't as gruff anymore and, if anything, it sounded slightly feminine.
I suddenly realized that Callie's boyfriend, Bobby, was actually her girlfriend, Bobbi.
Callie's pussy grabbed onto me tight, despite the sudden fading of my erection. I didn't fancy being in the middle of a domestic dispute.
"Get the fuck off of him!" Bobbi screamed as she reached her flannel-clad arms around Callie, pulling her reluctant body away from me and tossing her on the floor.
Bobbi was all of five and a half feet tall but with broad shoulders. She had gray-blond hair cut into a short mullet, long enough to go over the collar of her flannel coat. Had I been able to look all the way down her, I'd have seen her shitkicker boots under her ragged bluejeans.
I was stunned, but not so much that I didn't instinctively cover my quickly deflating hard-on with my hands as she stepped up to me. "You think it's funny?" she asked, "My girl, cheating on me?"
"Funny" was the furthest thing from my mind at the time and I'm sure I had a look of embarrassment on my face rather than anything close to a smile. Maybe a grimace.
"Maybe you think it'd be pretty funny if you got fucked," she said.
Before I knew what was going on, she undid her belt buckle with one hand while hoisting one of my legs over her shoulder, pulling me to the edge of the massage table, with the other.
She let her jeans drop to the floor in a clatter, hooked her boxer briefs with a thumb and yanked those down to reveal a large, flesh-colored strap-on cock. The sight would have been more disconcerting on a less-masculine woman. As it was, Bobbi looked pretty natural with a cock between her legs.
Still in the heady space of sex, it took me a few seconds to figure out what she was going to do. She spit on her hand and rubbed the shaft of her hard rubber cock. Once I realized that she was going to fuck me, I started struggling to get away.
She was having none of that. She held tight to my leg grunting, "Hold still, little bitch. I'm gonna pop your cherry."
She pulled me closer and I felt a searing pain tear through me. "No, please! Stop!" I gasped, begging. Her cock inside of me, she grabbed my other leg and started pulling me band and forth on her. It felt like she was tearing me in two. Loud sobs filled my ears and I felt bad for Callie but, when I looked over to her, I saw she wasn't crying. It was me. The pain was terrific. But, hidden behind the pain, was something else.
"Oh my god, Callie," Bobbi said with her slight Southern drawl, "You picked up a faggot. Look at his little cock."
I looked down to see that Bobbi was right. Through my tears, I saw that my cock was sticking straight up, a small bead of precum at the tip. I felt mortified that I could be enjoying this somehow and wondered what the hell was the matter with me.
I looked up to see the look of determination on Bobbi's face as she pounded my ass. She was thrusting like her cock was the real deal, her face getting flushed and sweaty from the effort. She was grunting like I'm sure I'd grunted as I had fucked girls in the past, but I was the girl now.
I looked back up to the ceiling, willing it all to stop, realizing that my body was no longer feeling pain now. I was awash with a discomfort topped with pleasure and lust. I couldn't believe it, but I was enjoying Bobbi's cock pummeling my ass. This thought ran through my head before the world exploded in white light. I didn't even know I was close to orgasm but there it was, overtaking me.
I felt the beads of sweat from Bobbi's face landing hot on my stomach, mixing with the puddle of cum that was collecting there. She yelled, "Oh, shit, yes!" and started jack-rabbiting inside of my ass as she came, too.
She pulled out of me and I felt the void where her cock had been crying out for her to be inside of me again. I turned on my side, away from Callie, and brought my knees up to my chin, balling myself up and crying out of shame and release.
Bobbi left the room and Callie followed quickly behind. I could hear them arguing in the front room as I tried desperately to shut out the world around me. More than anything, I was reeling from a horrible sense of confusion. I didn't understand how Bobbi could make me cum the way she did and why I had enjoyed it at all. I didn't want to admit it to myself and couldn't let anyone else in the world know what had happened.
Eventually, the tears stopped coming. I sat up, the cum crusty and dried on my stomach, the blood from my behind smearing the white towels on the massage table. I found my clothes and began to dress.
Callie must have heard my movements. She came to the door and stood there, "Don't worry, Bobbi's got it all out of her system. She's had a few drinks now."
I didn't say anything because there wasn't anything to say. Callie had a bruise under her right eye where she had either hit something after Bobbi had thrown her or where Bobbi had possibly hit her. I just nodded and kept dressing.
I tried to leave the room but Callie was in my way. "Hey," she said, putting her hand on my arm, "It's okay. It doesn't make you any less of a man."
I shrugged off her hand and pushed past her, keeping my head down. I walked quickly to the front door and, as I fumbled with the lock, I heard Bobbi behind me slur, "Come back any time, faggot boy, and I'll cornhole you again."
I came back the next week and she was good to her word. But this time, instead of begging for her to stop, I begged her to fuck me.