tagTranssexuals & CrossdressersUnconditional Love Ch. 09

Unconditional Love Ch. 09


The week of our vacation went by a little faster than I would have preferred it to, but it was all a lot of fun regardless. It was our final day down in Wildwood, New Jersey and we had spent most of the morning packing our things so that later we could go up to the boardwalk one more time and not have to worry about not having anything ready to go in the morning.

After my threesome with Allie and Christy, I found myself wondering why I had ever neglected anal sex in the first place. Sure, that had been a common thought on my mind since I finally let Alison fuck me, but letting Christy fuck me left me wondering even more what the hell my problem had been.

It had been a pain in the ass, quite literally at first, but I had adjusted to the feeling of her huge cock and I ended up enjoying the entire experience with those two. Alison had made sure that I understood that this was a one' time thing only though, and she seemed pretty damn serious about it too.

As much as I knew she had enjoyed herself that night to, I knew she did not want to have anything like that happen again once we got back to Philadelphia.

Everything was supposed to go back to normal when we got back home,

The rest of the week, Jamie had been acting kind of strange though for reasons I could not quite understand. She was not exactly ignoring me, but every time we were around each other, she seemed quiet and distracted. That was really the best way that I could describe how it seemed to me.

Then there was an incident the other night, the night after the threesome actually in which she had walked into our motel room and forgotten to knock on the door first; Alison had been in the shower and I was laying in bed naked having just finished having sex.

Jamie got a full on view of me bare ass naked on the bed and before she could duck out of the room, Alison came out of the shower also completely nude shocking the girl even more.

She laughed about it later and insisted that it was no big deal apologizing to the both of us; Alison wasn't' angry and neither was I, we all seemed to find it pretty' funny. Jamie had been quiet ever since we talked about it though and I was actually starting to get worried.

Then there was the way she had been dressing; she had been dressing in all these' sexy clothes that showed off lots of cleavage and at first I had not really thought much of it, but now I was starting to wonder what the deal was. It wasn't' like I had seen her flirting with any guys, so why even bother dressing that way in the first place; she sure seemed to be all around me though.

All signs pointed to one thing; I was beginning to think that Jamie was trying to flirt with me, or at least trying to get my attention. It seemed odd, of course because we had known each other for so long that I had never imagined the two of us being together.

With no real proof of that though, I had shrugged it off and was hoping to try and' forget about it, one way or another. There was no sense in worrying about it unless she made a more' straight' forward move which would leave me with more than enough proof.

It was around 11:00am and I was sitting in the motel room watching TV with Alison. In a little while we would be heading down to the beach with Joe and Jamie, Christy would be going up to the boardwalk by herself. She had gone to the beach the day before and was looking to go off and do her own thing today, so we offered no complaints not wanting to hold her back.

I smiled over at Alison and she smiled back, as I started thinking about how much sex we had, had this past week. We'd' fucked more times while we were here then we had back home in Philly the entire time we had been dating. It was amazing how many times we had gone at it, at night, in the morning and a few times' in between we were like rabbits or something.

It had all been really' good though, perhaps some of the best sex I had ever experienced.

"So did we have fun this week, or what?" Alison asked me.

"Of course I did; in more ways than one. Did you?" She sat up on the bed and stretched, leaning back against the headboard and grinning over at me. "I had a lot of fun," she replied. "I just wish we didn't have to go back home and try to act like certain things didn't happen."

"You're talking about the threesome?"

She nodded her head, and I found myself wondering why she would say such a thing. It was after all, her who said that we would act like it had not happened once we got back home it was her' who made it clear that she did not want me getting it on with Christy again after our vacation ended. That it had all been a one' time thing; so was she now trying to tell me she had changed her mind or something?

"Yeah...I don't know it was just really nice. I use to do that kind of thing with Christy all the time when we were younger' we would hook up with people and fuck the hell out of them together. It was nice to do it again and this time with someone I actually know and love involved, made it even better."

"So what, are you saying you would want to do it again?"

She laughed and slid over to the edge of the bed with an odd grin on her face.

"I don't know," she said seductively. "Probably not with Christy; she has to get her shit together and find a boyfriend sooner or later, and the more I let her have dibs on my boyfriend, the less time she'll spend looking for a guy of her own."

I laughed, taking a sip of my coffee and leaning back against the wall behind the chair I was sitting in; Allie really wanted to see Christy find a new boyfriend, she wanted her to be happy. Hell, even I was hoping that at some point she would find someone who would make her smile, the way Alison and I made each other smile all the time.

It sure would be nice to see something good happen for the one who had helped us out with our problems. I wondered though, if she wanted to have another threesome at some point in the future but not with Christy then who would she want to do it with, and why was she bringing it up now after making it seem like she was not interested at all.

"So who," I asked, not sure if she would continue if I did not say anything.

"Oh I don't know," she said innocently. "Maybe...your friend Jamie,"

What the' hell was she smoking, I thought; was she on acid or something? When in the hell had she come up with such a crazy idea of having sex with me and' my best friend at the same fucking time. Not that I could blame her for wanting a piece of Jamie, hell, even I knew that girl was hot as shit. Especially, the way she had been dressing lately; if she was trying to get my attention she'd' had it all week and probably did not even realize.

Putting all of that aside though, Alison did have a dick, she still had that male sex drive so I guess it wasn't' that big of a shock, but I had not realized she was interested in women really. I thought she only liked men,

"Your' kidding right; you want to have sex with Jamie?"

"No, I want the three of us to have sex together...if your' up for it,"

"What makes you think she would want to?"

Alison started laughing, she rolled off the bed and walked across the room to the bathroom and I got up off the chair and followed her. I walked into the bathroom behind her to find her standing over the toilet, holding her dick and relieving her bladder.

"Your blind as a bat Mike you know that? I love you with all my heart, but sometimes you are just so god damn blind."

"What the hell is that supposed to mean?"

She shook her dick and slipped it back into her pants zipping up and flushing the toilet then turning around and leaning against the door' frame, mere inches away from me.

"Jamie has a thing for you,"

There it was; my own fucking girlfriend was sitting here trying to tell me that my best friend had a crush on me. Of course, I had suspected it even before I started dating Alison, but I had always tried to shrug it off, Especially, after I started dating her; I didn't know what else to do really, at that point I figured it was too late and I wouldn't' ruin what I had with Allie anyway.

I was in love with her; so I had tried not to think about how Jamie felt and in the process we had actually sort' of drifted apart. That's' kind of why I had been happy that she was coming down to Wildwood with us, because I wanted some time to catch up with my best friend.

"What makes you so sure?" I asked.

"It's all over her face; she's probably always liked you, I see the way she looks at you, the things that she does for you and personally I think she's tired of just being there to listen to you and give you advice. Have you seen the way she's' been dressing this whole week? She's fucking hot!"

I laughed, finding it hard to believe that my transsexual girlfriend had just told me she thought my female best friend was hot.

"Alright, yes I've noticed. I was just trying not to think about it really, I don't know why she's been acting this way all week."

"Doesn't matter," Alison said. "Just watch while we're at the beach; I bet you anything she'll do something else to show that I'm right. Just promise me one thing will you?"


"If she makes a move, you can hook up with her; but I want to be involved."

Hook up with her; I would have expected the jealous side of Alison to come up at even the mere thought of something like that happening. Here she was though telling me that I could fuck my best friend as long as she was' allowed to join in and fuck her to.

"Okay," I said, unsure of what else to say.

"Mike, let's be serious; do you want to fuck Jamie or no?"

She was asking me outright, and honestly I wasn't' totally, sure myself. Did I really want to have sex with her? I wasn't denying how hot she was or the fact that in the past I'd' had feelings for the girl. I just couldn't' help but wonder if this was some sort of a trap or something to see if I would stay faithful towards Allie, and if I hooked up with Jamie even though she said I could she would break up with me later on.

We got to the beach and set up a spot, with an umbrella embedded in the sand and laid out o beach towel for us to sit on if we wanted. The first thing we did as soon as we were set up was make our way out to the water, jumping right in and enjoying the fact that it wasn't too cold and it wasn't too hot either.

After about twenty minutes or so of swimming, I made my way back to land and found that Jamie was in the process of doing the same thing. We walked back to the spot where we had set up and grabbed our towels, drying off and then sitting down side by side to enjoy the warmth of the sun.

"The water is great," Jamie' sighed, laying back on the beach towel and closing her eyes as the sun beamed down on her. I sat beside her and glanced over, taking in her beauty. I sized her up, noticing her perfect breasts; that damn bikini she was wearing was a serious turn-on and I felt my cock stirring in my swim trunks hard as a rock.

"Yeah...feels really good," I replied after a few seconds.

"So how have you and Allie been doing?" she asked me.

I cleared my throat, trying to hide my erection and laid down next to her, smiling over at her.

"We've been good," I said. "This vacation has been a lot of fun; really good opportunity for the two of us to let out a lot of stress."

"You know, those motel walls are paper thin," she joked. I understood right away and blushed then laughed and she laughed as well as she sat up and ran a hand through her wet blonde hair. "You really sounded like you were enjoying yourself the other night; you and uh...Christy got it on right?"

"Well...not just the two of us. It was sort of a threesome,"

She giggled and moved closer to me. I wasn't' sure what she was really doing, it had to be awkward for her to talk about this with me and yet here she was bringing it up as though it were casual conversation, an every day event that people talked about on a regular basis.

"How big is Christy?"

"Big enough," I laughed. "Bigger then Alison...it hurt at first actually."

"Wow...you okay?"

"Oh yeah, I'm fine; there's no such thing as to much lube, trust me," I joked.

"You know Mike," she said staring off towards the ocean now.

"I really am glad I got to come out here with you guys; it's been a lot of fun hanging out with everybody this past week. Especially with you, we use to be so close you and me and I just feel like we have drifted apart. I don't ever want to lose my best friend, and I'm really happy I got to spend this week with you."

I smiled, maybe it wasn't anything like what Alison was trying to make it seem like it was after all; maybe Jamie was completely innocent and she really had just been trying to enjoy her time with her best friend and her other friends as well. I didn't' mind at all, she was right we had not been as close as we had been six or seven months ago.

We'd' drifted apart, something we had always sworn we would never let happen and yet we had let it happen. So' catching up on lost time was something that the both of us were pretty happy to have been able to do; I put aside what Alison had said earlier, confident that there were no sexual intentions being worked on in Jamie's mind.

Somewhere during the course of our conversation though, I had forgotten about my erection' which was apparently only halfway gone by this point in time; it was down just enough so I could uncross my legs without having to worry about Jamie noticing it at least.

Until of course' she leaned over and gave me a peck on the cheek. We locked eyes and the next thing I knew she leaned over and pressed her lips to mine kissing me full on,

I was shocked at myself, not because she was kissing me but because I was offering no protest.

Sure, Alison had said it was okay, but was I really letting her kiss me without trying to stop her,

She slid' her tongue into my mouth and I responded with the same action as she moved closer to me some and I ran my hands up and down her back. She grabbed my one hand and moved it to her left tit and I got a perfect feel of her breasts, my cock throbbing as I did so. She broke the kiss and smiled down at me,

"When we get home, I want us to go back to the way we use to be. Okay?"

"Yeah...yeah of course,"

She smiled at me and pushed herself up to her feet, turning around and stretching. She was giving me the perfect view of her beautiful ass and a nice little glimpse of side boob.

"I'll be back," she said smiling down at me. "I'm off to the bathroom."

I watched as she walked off towards the nearby restrooms, her ass swaying back and forth and my cock straining in my swim trunks. I leaned my head back against the soft sand and groaned in frustration, trying to comprehend what I had just done; I didn't' notice Alison as she walked across the beach, following Jamie from a distance towards the bathrooms. I looked up just in time to see them both slip into the room and found myself wondering what ill intentions my girlfriend had now.

Jamie's POV

I walked into the bathroom and opened one of the stall doors, stepping inside. I lowered the bottom half of my bikini and sat down on the toilet seat, resting my chin on my hands and smiling as I thought about that dumbstruck look on Mike's face that he'd' had before I walked away.

I laughed at myself, realizing how evil I was being trying to seduce my best friend who happened to have a girlfriend, sort of a girlfriend. After all, Alison wasn't' necessarily your typical girl, what with having a dick bigger then Mike's and all.

I almost felt bad for trying to seduce her boyfriend; but I wanted him so bad,

As I started thinking more about what it would be like if I actually managed to get Mike to sleep with me, I started wondering what the aftermath would be like. Would he be angry at' me, He couldn't' get mad at me; he had his own free will in the matter, he could say no at any time and I would stop.

He couldn't' get mad at me for the kiss either, he had kissed me back. Oh god, he had kissed me back; I was shocked but had not taken the time to let that register until just now when I actually had the time. I wasn't' going to rape him or anything like that; I just wanted to see how far he was willing to go with me before he would back off.

If he happened to be willing to go all the way with me, then so be it; so far he seemed willing to at least mess around a little since he had after all kissed me back.

I realized then though, what would happen with Alison if she found out later? Would she hate me? I did not' really want Allie to not like me, but at the same time we weren't' exactly friends so it would not hurt all that bad if she did hate me.

Then again, I had to admit Alison wasn't' half' bad looking herself; hell, if I were a lesbian I'd be trying to hit on her. Well maybe if I were bisexual if I were a lesbian I probably would not' want her sexually seeing' as she did not have a pussy.

I hadn't' been able to stop thinking about how she was actually relatively attractive, since the other night when I had overheard her, Mike and Christy having sex. Then there was when I walked in on Mike sprawled across the bed bare ass naked and Alison came out of the shower with no clothes on either. I got a full view of her cock, damn was it big and I would' be so turned on I just took off running.

They thought it was because I didn't' want to intrude, really it was because I knew if I walked in there and tried to have sex with them both it might not end well. So' I had to get back to my own room to take care of my own sexual tensions by myself even though I knew what I wanted.

My thoughts were' interrupted by the sound of the bathroom door opening and shutting and footsteps moving across the floor. I didn't' think anything of it at first, until someone spoke up and called out my name.


I jumped in surprise, but relaxed a little when I realized the voice actually belonged to Alison.

"Hey, I'm in here."

"Thought I saw you come in here; I had to go to," she answered.

I heard the stall door next to mine open and shut and Alison sighed as she sat down on the toilet and proceeded to do her business as I was doing mine.

"It's such a beautiful day," she said. "Perfect for our last day out here, don't you think so?"

"Yeah, it is. I don't even want to go back to Philly; it's too beautiful out here."

Alison laughed and I heard the toilet paper dispenser being' pulled at followed by the shuffling sound of her standing up and pulling up her bottoms. She flushed the toilet and I could see her feet under the stall as she walked out and over to the sink to wash her hands.

I tried to start thinking about Mike again, but I was distracted for some odd reason; I did not' know why, but I couldn't' help but wonder what it would be like to see Alison naked again.

"I noticed you and Mike got some time together this week,"

I froze, afraid that she may' have seen the two of us sitting together a few minutes earlier. Not that, that would be bad, but I was worried she may have seen me as I gave him that peck on the cheek; I wasn't so sure how she would react to that if she had seen it, or even the next thing that had happened.

What if she had' seen me kiss him? That hadn't' been some simple little kiss between friends, that was a full on make out session. I was even a little surprised that he had kissed me back but I could only imagine what would happen if Alison had seen it and furthermore if she realized he hadn't tried to stop me.

"I just wanted you to know I'm glad to see it," she said.

"I know how close you guys are and I was kind of worried that sooner or later you might stop talking all together. I'm really happy to see you hanging out again,"

"Yeah, me too," I replied.

Report Story

byWhiskeyIsGood© 2 comments/ 33638 views/ 34 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: