tagTranssexuals & CrossdressersUnconditional Love Ch. 06

Unconditional Love Ch. 06

byWhiskeyIsGood©

Alison arrived at my house at the exact time she said she would be there. I let her in through the back door and pulled her into my arms, giving her a passionate kiss on the lips. I was glad to see her; I was sick of all the arguing' and was looking forward to spending a weekend with her where there would be no drama or fighting. She kissed me back and then pulled away and tossed her bag onto my bed, walking over to it and started to unpack her stuff.

"Came prepared I see," I joked with her.

She laughed as she pulled out a pair of pajamas and a couple pairs of day clothes. She brought along a bottle of her own soap and shampoo and what looked like some sort of massage oil. She turned back to face me after she finished unpacking and smiled.

"Well I did say I had something planned,"

That she had, and I had been waiting for it ever since she had said it, wondering what the' hell she was going to do.

"Are you ready for your surprise?" she asked.

"You know I am,"

She wrapped her arms around me and kissed me on the lips, I kissed her back and felt my cock beginning to grow hard in my pants. I could not wait to fuck the hell out of her. I was confused though; just how would this be any different from any other time that we had sex.

She was making it seem like she had something in store that would be unique, but I had no idea what she could possibly do to make that happen.

"Why don't you get undressed and lay down, while I go in the bathroom and freshen up," she said.

"Okay," I replied giving her a quick kiss before she grabbed her bag and walked into the bathroom shutting the door behind her.

I took a deep breath, hesitating for a moment, then' pulled my shirt off tossing it to the floor. I followed with my pants, shoes and boxers before collapsing onto the mattress bare ass naked. All that was' left to do now was sit here and wait for her to come out, and for whatever she had planned.

Alison's POV

Once in his bathroom, I set the bag down on the floor and got to work. It was a small bathroom, so I had to be careful not to bang my knee against the sink as I slipped out of my clothes and stood naked in front of the mirror, my cock slowly becoming hard at the very thought of what I was about to do to Mike.

I took the time to brush my teeth and apply a little bit of perfume to make sure that I smelled good; I also applied some cherry scented lotion.

The next step was getting dressed to get undressed. I never usually wore lingerie but seeing as this was such a special occasion I figured what the hell. Finally' after only fifteen minutes, I came out of the bathroom to find him sprawled out across his bed, completely naked with his cock already standing at full attention waiting for me.

I smiled, and laughed, thinking this was going to be a lot of fun on both of our ends. Mostly mine though of course.

Mike's POV

I had never seen her look so beautiful in the time that we had been dating, but right now' she was fucking hotter than hell itself. She walked across my room like' she owned the place, crawling into the bed and moving over top of me.

I could smell that perfume she always wore that I loved and a faint hint of the cherry lotion she knew turned me on every time. She kissed me and I felt my cock straining as we started to make out; I just wanted to fuck her, but she had gone through all this trouble so I was going to put up with the foreplay to.

Through her undergarment's I could feel her own cock pushing against mine, obviously very hard and I knew that we were both sick of just kissing. I flipped her over and tore her panties off, her cock sprang free and I leaned in kissing her on the lips and then making my way down her neck and chest.

I kissed down her chest and stopped to lick one of her nipples, sucking it into my mouth and gently biting it; I earned a moan from her and continued making my way down her stomach. Down past her navel to her groin, I groaned at the smell of the cherry lotion as I reached my destination.

I grabbed her cock and' started stroking it, while licking and sucking at her balls and ran my tongue up the length of her erection to the head of the shaft before flicking it with my tongue. She sighed and I continued on, wrapping my lips around her cock and taking her to the back of my throat.

I had grown use to performing oral sex on her by this point, so I really did not have much trouble doing it anymore. I was glad for that though, because it meant I could really go all out on her without having to worry about gagging.

My head bobbed up and down taking her cock in and out of my mouth while playing with her balls with one hand and her tits with the other. She was starting to get into it, thrusting her hips up and down pushing her cock down my throat and I savored the taste, groaning, as my own dick started getting harder.

I could tell by how fast she was moving her hips and how loud her moaning was starting to get, that she was getting close to her orgasm. She stopped short, pulling her cock from between my lips and shoved me onto my back climbing on top of me and shoving her dick back down my throat. Her balls against my chin and tits hanging over me, I was in heaven in this angle and could not wait to make her cum all over my face.

It felt weird to me that I was willing to do all of this, I even welcomed her doing this to me, yet I still felt uneasy with the idea of taking it in the ass from her.

"Oh shit, I'm going to cum," she moaned.

I reached around and' grabbed her ass pulling her cock deeper into my mouth and moaned as I felt her cock twitch and start to shoot cum down my throat. I swallowed every drop as she gasped for air, gripping the headboard as she unloaded her balls in my mouth. When she finished I gasped for air as she pulled her cock from my throat and wiped the head all over my lips, before moving down and kissing me and' now it was my turn to take control.

I flipped over on top of her, spreading her legs and moving in so that my erection was' pressed up against her ass crack. She sighed as I captured her lips, sliding my tongue into her mouth while probing her ass for a few minutes before pushing the head carefully in for just a second.

She grunted as I pushed in and stayed there for a moment then pulled back out and pushed back in again. I remained inside of her this time, and started pushing inch by inch into her ass until I was' buried up to the balls inside of her.

Alison moaned, digging her nails into my back as I started out nice and slow wanting to take my time; I wanted to make this last as long as possible.

I started thrusting in and out, nice and' slow both of us moaning in pleasure as I felt her cock starting to get hard again from the prostate stimulation. As I felt her breathing become faster and heard her moans getting louder, I began to pick up the pace thrusting in and out a little faster and the bed started to creak underneath of us.

She wrapped her legs around me, pulling me deeper into her and I started really getting into it now thrusting in and out with great speed. I was fucking her with long hard strokes, flesh slapping against flesh.

We were starting to sweat now and I could feel my heart rate picking up moving faster and faster as I started to feel myself getting close to Cumming. I stopped, and pulled out not wanting it to end that soon. She must have got the hint because she pulled me in to kiss her on the lips and we just made out for a few seconds before she rolled over onto her hands and knees and I resumed fucking her.

I pushed right back into her, easier this time than the first time and gripping her by the hips I started pounding her ass now.

Again, I felt the pressure in my balls starting to build up and I knew I was about to cum, when she pulled away from me and I slipped out of her ass. She pushed me onto my back and I groaned in disappointment, but she made it clear there was nothing to be upset about when she mounted me and guided my cock back into her again.

She was riding me now, bouncing up and down on my hard cock, grabbing at her tits and moaning my name.

Her body went into a fit of spasms suddenly and her throbbing dick began to spew a load of cum all over my chest and my face, and that was enough to throw me over the edge as I gasped for air and started to cum,

I moaned, thrusting upwards deep into her asshole and started pumping her full of my' cum until I had nothing left to pump and she collapsed on top of me.

We were both out of breath now and covered in sweat, as we lay together for a few long minutes before she lifted herself up off my cock and dropped down on the mattress at my side. As my breathing began to return to normal, she propped herself up on her elbow and started tracing circles around my nipples with her finger while smiling at me.

"That was fun," I said.

"Did you like the lingerie?"

"Of course; it was sexy."

"I'm glad,"

"So was that your big surprise? I know you've never worn it before."

She smiled and laughed, turning over and grabbing the bottle of massage oil off the nightstand. I had all but forgotten about that, but now' I recalled her taking it out of her bag with her other stuff when she had first arrived about an hour ago. She turned back over and popped the lid open and motioned for me to roll over onto my stomach for her.

"I wanted to try my hand at giving you a little massage; I hope you don't mind."

"Of course not," I replied. "No harm in a good back rub,"

If only I had a clue what she really had up her sleeves.

Alison's POV

So far so good, I thought to myself as he rolled over onto his stomach and I smiled seductively; he could not see that smile though' which was fine by me.

I had to say though, I was quite tired from the fucking he had just given me; it had been one hell of a ride quite literally. I had already gotten off twice in one night; but my dick was still so anxious to get a taste of his asshole. I wanted this more than anything my night would not be over until I got it.

With Mike on his stomach, I proceeded to get over top of him and poured a large amount of the oil all over his back. I smiled as he jumped in surprise and laughed; it must have been cold, I probably should have warned him. No big deal though, he seemed to find it funny which made me laugh along with him. I took in the sight of his ass, and what a lovely sight it was.

I set the bottle down on the nightstand and started rubbing it into his skin, moving my hands slowly up and down his back and in a circular motion. This was my first time giving anybody a back rub, but judging by the sigh of relief he gave me, I figured it was safe to say I was doing it right.

Up and down' I worked my hands across his back, pushing and rubbing and realized just how tense he actually was. It must have been all the stress of the' arguments we had been having lately; I knew they were upsetting to him even though most of them were started because of him. I did not mean to sound like a bitch thinking that way, but it was the damn truth really.

I put that thought aside though; tonight was supposed to be a good night, this weekend was supposed to be a good weekend. Most of the fights we had were over anal sex, so hopefully' tonight would put an end to all those stupid arguments. I continued massaging his back and I moved my hands over to his shoulders and started rubbing them for a few seconds.

I pulled one hand away reaching for the oil and applying more to his shoulders before continuing to work it in. I felt his muscles which had started' off quite tense, begin to relax and I knew I must have been doing a really' good job because he was really starting to relax a lot.

"You like that?" I asked.

"Mm," he moaned. "It feels good; your' doing a great job."

I took that as a compliment, it was a boost in self-confidence for me and I continued rubbing as I felt my cock starting to get hard. Not rock hard, but I' was definitely getting a little bit of a semi-erection where a few seconds ago I had been almost completely flaccid. I worked my way from his shoulders back down to his upper back for a few moments and then after putting on some more oil I worked down to his lower back and he groaned.

I could feel he was really' tense there, his muscles seemed like they were all in knots and I wasted no time trying to work them out for him. In a circular motion, I moved my hands applying just the right amount of pressure and I felt the knots begin to loosen as his body relaxed more and more.

So far, the plan was working perfectly; he was becoming entranced in my attempt to make him feel good in a' none sexual manner and that was exactly what I had wanted.

Mike shifted slightly and I jumped in surprise, hoping he had not caught on to soon and that he was not about to put a stop to my attempt to get a piece of ass. I relaxed when I realized he was just trying to get into a slightly more comfortable position and we resumed my massage therapy right away.

I started working on his arms not, moving my hands up and down them and he sighed in relief as I did. Besides using this as a way to get what I wanted, as Christy had suggested, I was actually enjoying making him feel good.

I knew he was a hard worker at school and I knew he was the kind of person who usually was affected physically by stress so it made me happy to see that I could help take away some of that physical stress just by giving him a massage.

I was going to have to thank Christy big time later on,

It was fun, but now was the time to take it the next step forward; I could not dilly' dally around like this forever. Eventually, no matter how good it felt, Mike was going to want to get up so I had to move quickly. I applied more oil rubbing it into the center of his back and moving my hands up and down trying not to get to frantic with it for fear of not doing such a good job anymore.

Then slowly, I moved my hands down his back to his ass cheeks as Christy had suggested and I started massaging his cheeks. I expected some sort of negative reaction; this was the moment of' truth after all.

I received no negative reactions though, and took that as a sign that things just might go in the direction I was hoping they were going to go. I continued massaging his ass cheeks and moved one hand back up to his back again rubbing his back and his ass at the same time; Mike sighed and I smiled to myself as I started to get really' aroused.

I wondered if he was catching on by this point or not, it would be a major turn on if he knew what I was trying to do and did nothing to stop it but I would take it however' I could get it as long as I could get it.

After a few more minutes of steadily rubbing his ass and his back' I decided it was time to move forward even further. I took a deep breath trying to calm my nerves; it would do me no good if he was willing to let me fuck him but my anxiety prevented me from getting hard enough to do the deed.

I moved forward some and sat on his legs, my cock which had gotten a lot harder in the last minute and a half was now less than an inch or two away from the object of its' desire.

I moved both hands back up to his back and continued rubbing him up there and every couple of seconds I moved up a little more, my cock becoming closer to his asshole. He must have sensed what I was doing by now as I felt the muscles in his back begin to tense up again, but he offered no real sign of resistance; not yet anyway.

Now was the time, I thought, as I moved forward just a little more and leaned over him, my breasts against his back and my cock now resting against his ass crack. I knew he knew what I was doing now, as he gripped the pillow and I leaned in to whisper in his ear, "Relax,"

I started kissing him on the neck trying to help calm his nerves as my cock probed his asshole and I felt myself getting harder by the second. I was so close to finally getting what I wanted and despite the fact that he clearly knew' what I was doing by now, he was doing nothing to try and' stop me.

I kissed, licked and gently bit at his neck, sucking at it leaving a little hickey in the place of my lips. All the while, I gently probed his asshole with my cock for a few moments just to make it clear to him what I was going to do and to let him know he was running out of time to try and stop me.

When I was certain he was not going to stop me, I lifted away from him and reached over to the nightstand grabbing the bottle of lube and taking a deep breath. I popped the cap open and hesitated for a moment; I wanted to make sure he did not feel as though I were pushing him into this.

I would feel bad in the long' run if I found out later that he only did it because he felt like it would start another argument if he said no.

"Are you sure you want to do this," I asked.

"Yeah...yeah, it's okay."

"Really' your' not just saying that because you don't want to fight, right?"

There was a moment of silence and he sighed, trying to calm his nerves.

"I'm positive," he said. "I'm curious; I want to see what it feels like."

That was good enough for me, and I turned the bottle upside down squirting a large glob of lube all over his tight virgin asshole. He jumped in surprise at the cold fluid as he had done earlier when I first applied the massage oil.

I carefully rubbed the lube in and slowly inserted my index finger into his asshole, pushing it all the way in to the knuckle and rubbing his prostate gland. He jumped again as I touched the gland and I waited to make sure he was alright before continuing; I was just trying to get him ready. If anything, the one thing that worried me most was the size of my cock.

Being his first time, I hoped that it would not cause too much pain, both because I knew it would cut our session short and because I did not want to cause him any kind' of harm.

Mike's POV

I was a bit shocked at what was going on right now, more shocked at myself that I was allowing it to take place at all; every time she had attempted this in the past I had rejected the idea. She must have been afraid I was only doing it to avoid arguing, because she had stopped to make sure I was okay with it.

I was okay with it; that was the scary part. I was not doing this so we would not fight, the god honest' truth was that back massage had really turned me on and the feeling of her sitting on my legs with her cock up against my ass had actually gotten me kind of curious and a lot more aroused. Now as I felt her slowly insert her finger, I felt the anxiety begin to kick in and the urge to push her off and change my mind.

I ignored it though because I really did want to try this; I could not always turn her away. Life was full of surprises, or at least they said, for all I knew I could end up enjoying myself if I would only open up and allow myself to try this.

I jumped in surprise, something felt really' weird; like a burning sensation in my cock almost like' I had to piss. She must have been touching my prostate gland; I had heard all about that part of the male body.

When it came to sexual activity, if it was stimulated properly it could supposedly spark an orgasm more powerful than an ordinary one and quite similar to the kind that you could trigger in a female by playing with their G-spot.

I wondered if all' of that was really' true or if it was just a load of bullshit. She continued rubbing me in that spot though and suddenly I was starting to think maybe it was not a load of bullshit at all; I moaned and felt my cock getting really' hard extremely fast. Back and forth, she rubbed my gland and I gripped the pillows tightly biting my lower lip at the sensation.

She pulled her index finger out just slightly, and I was about to groan in disappointment but I relaxed when I felt her push back into me only this time it felt different. I felt my asshole being' stretched and I realized that she had pushed her finger back into me but it was not just one finger anymore, this time it was two fingers.

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byWhiskeyIsGood© 7 comments/ 33865 views/ 16 favorites

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