There was this “lonely house wife” posting on CL, so – me being a “lonely husband” replied because I was curious. I didn’t think I had a chance in hell because as we all know responding to an ad on CL is either spam, fake or just never pans out. I emailed her, told her I was in the same boat as her and that my wife was okay with me playing around as long as I was safe about it. I really didn’t expect a reply back but I got one the next day.
The thing about hooking up with women from CL is, usually they use their real names. I’ve been with 4 women from CL, all of them used their real names. I looked her up on face book and got better images of her then what she sent me, easily done. Sure, she looked attractive, face was maybe a 5 but she was – thin, smallish boobs, likes fast cars. Obviously the husband can’t handle her needs.
We emailed back and forth, she wanted to exchange numbers for texting but I told her that was the best way to get caught. Obviously she was very new to fucking around behind her hubby’s back. She agreed and we decided to meet for coffee. We met at a small diner, nothing special. She was wearing high heels and was just a few inches shorter than me with them on (I am 6ft 2inches). We connected, she didn’t want to hear me complain about my wife and she said she wasn’t going to complain about her husband either. She just wanted “dick.” I laughed, I was fine with that. She said she had 3 kids, two in collage. With a body like hers, it didn’t even look like she ever had kids to be honest.
We went to the parking lot and started making out. She told me she wasn’t “a car type gal” and she wanted to get a room. Fuck yeah, I’m in.
“I don’t have any condoms,” I told her.
She shrugged, “I’m clean, and you’re clean too right? We went over this in emails.”
She was kind of snippy about it. So I snapped back, “good, because I hate pulling out.”
She smirked.
We ended up at a Motel 6, it was the closest motel to the diner. As soon as we were both in the room we disrobed and started oral. I’m not huge, I’m only 6.5 inches but I am thick. She took my cock like a pro in her mouth. I licked her pussy, sucked on her tits (they were fake). I saw little cut marks in the sides of them – she must have been pretty fucking flat chested I thought. She only has a small B cub, nothing big but they were perky as fuck.
“I need you in me,” she moaned. So I stuck it in her. Now, I know tight pussy and loose pussy, I’ve had both. This pussy was fucking TIGHT. It gripped my dick like a fucking vacuum chamber.
“Holy shit, you’re tight.” I said sliding in and out of her.
“Fuck me, FUCK ME HARDER.”
I was on top of her, railing her hard – I felt my nuts starting to tighten and it wouldn’t be long before I was dropping my seed in her. I wasn’t even going to ask. I was just going to do it.
Her nails dug into my back and I slammed into her harder and harder as she screamed in orgasm.
“HOLY FUCK I’M CUMMING,” I yelled as I erupted inside her. She wrapped her legs around me, embraced me with her arms and pulled me tightly against her. I could feel her milking every inch of my cock for cum. I collapsed on top of her.
“Kim, holy fuck…” I said.
I moved off of her. She wasn’t the cuddling type. She just looked at me and smiled.
“Do you want more of me?” she asked.
“Hell yeah I do! You felt perfect! You’re pussy is… holy shit, it’s the tightest pussy I’ve ever had.”
“Good, then the surgery worked!” she exclaimed.
Surgery? Huh? I just came deep inside her, my mind was not even thinking about anything rational… “surgery….”
I played with her pussy and tits a bit before leaving. We had a great time. I kissed her, she groped my cock through my pants and we left.
I emailed her later thanking her about the wonderful time and wondered when we would be able to hook up again. Then, in the back of my mind – “surgery” popped up. Holy fuck, what surgery? Did she have her pussy tightened? Good for her! But something bugged me… so, I asked what surgery she had.
“Hi,
I guess this isn’t easy to hear and I am not proud as only my husband and my family knows. I am post op trans. I had vaginoplasty surgery. I am still able to cum because they saved my dorsal nerves because of the technique they used called penile inversion. I hope you are not pissed off at me. I like you a lot.
Kim”

What do you say to that? She was totally passible as a woman! COMPLETELY. There wasn’t one moment where I was like, “hey this might be a dude!” I’m not homophobic, and I had a great time but I do wish she would have been honest up front. If she’s not honest about this shit, what else isn’t she telling me? Plus, she isn’t even being honest with her husband… If I told my wife about this, she’d laugh at me. What would you guys do? Would you still fuck her?? I haven’t written her back yet because I’m still like WTF.

I confess to getting hard and turned on by my masseuse.

I know what your thinking just tip her and get the happy ending. Well Elle not that kind of a masseuse. Elle is licensed in therapeutic massage and is phenomenal at her work. My wife and I are both her clients. She works out of a legit chiropractic office so her services are covered on our insurance. My wife recommended chiropractic and massage massage therapy after I suffered a sports injury a few years ago.

The chiropractor had just aligned my spine. I was in waiting room. I had a nagging thought that I had forgotten something. Elle came out moments later to retrieve me. She greeted me with her typical warm smile. Elle was 24. She had a svelte toned and athletic body. Brown hair typically put up in a ponytail. Blue eyes and dimples. She was girl next door pretty. Elle motioned me towards the back rooms. I followed her down the long hall. I was watching her ponytail sway from side to side when my attention was drawn to her perfectly toned ass clad in yoga pants. The tight fit of her yoga pants left little to the imagination. I was fascinated with each perfectly outlined ass cheek rise and fall as her hips swayed side to side. Her walk was purely feminine. I was having a hard time finding a panty line when we arrived at the door to her room. My eyes lingered a bit too long and Elle caught me staring. She opened the door and invites me in wordlessly with a friendly smirk.

SHIT! I realized what I had forgotten. I didn’t pregame. Pregaming in this case meant masturbating before my appointment. A practice I began after an untimely, embarrassing erection I had with my original masseuse shortly after I began massage therapy. I got the impression that I had offended this masseuse so I apologized. After another awkward appointment with my original masseuse, she announced that she was getting married and her fiance got a job out of state. That is when both my wife and I began seeing Elle. Turns out that Elle was a much better masseuse anyway.

Once inside the room Elle asked, You want me to concentrate on your lower back and hips still? I nodded. She continued, You know the drill. Get undressed and I'll be back in a a few minutes.

She closed the door behind her as she left. I quickly undressed. I got on the table naked and face down. I pulled the sheet over me. I put my face in the saddle shaped cradle. A minute later I heard a soft knock at the door with Elle asking if I’m ready. I respond with a Yep. I hear the door open then close, Elle pulled the sheet down exposing my back. I felt her warm oily hands on my upper back moments later. Elle has a touch that is deep, slow and sensual. She intuitively skates the line between pain and pleasure with every movement. My stress melted away. My mind wandered to very recent memories of Elles beautifully shaped 24 year old ass. I mentally slap myself by recalling that I have a daughter her age. Never had I once thought of Elle sexually. No…. Really. I have admired her youthful beauty but never considered having sex with her before. As her hands moved down my back I force any notions of Elles sexuality out of my mind.

My mind wanders……. ***I recall a warm summer day. I’m in a field near my house with my childhood friend JoAnn. We had just finished swimming. We wanted to warm up and get some sun. We followed a deer trail through the yard high tall grass to a deer bed, where the grass had been flattened. We spread our towels on it and layed down. I was enjoying the warmth of the sun on my back when I felt something irritating it. Was it a bug? I shooed it away. I discovered it was a piece of grass that JoAnn was intentionally tickling me with. I told her to knock it off, It itches. Joann continue till I pulled it roughly from her hands and threw it away. I put my face back down in my arms.

Moments later JoAnn says, Sorry.

I answer with a shrug. JoAnn starts gently scratching my back where she had tickled me with the grass.

I let out a pur saying, now that feels good.

JoAnn’s light scratching turns to a light touch. It felt electric. I was being touched in areas that usually didn't get touched. A contented, Mmmmm escaped my lips. As she gently moved her touch slowly on my back. I turn to look at her. I notice the wet bright yellow panties of her bikini clinging to every curve of her vagina. I would come to know this as camel toe later in life. It felt I wanted share the sensation of touch with her.

Hey Joann, this feels really good. Let me do it to you.

She sprung up quickly, reached around her back and adeptly unfastened the back of her bikini top while holding the front against her so it wouldn’t fall off. She held it tight against her while she laid on her belly. Her naked back facing me waiting to be touched. I mimicked the movement of her touch on my back on hers.

JoAnn says, Oooo That really does feel good. I wish girls could go around topless.

Me too, I joke.

She continues, I remember when I was little girl and I didn’t have to wear a top when swimming. I felt free.

I suggested that she take her top off, No one will see in this tall grass. I won’t tell anyone.

JoAnn said, This doesn’t mean I want to have sex. You’re just my friend. Not my boyfriend.

I nodded and crossed my heart telling her, I won’t do anything you don’t want me to do, Promise.

JoAnn turned over and sat up. The loose top pressed against her chest covering her boobs. She conspiratorially looked in all directions making sure that the tall grass gave us enough privacy. She slowly removed the covering from her breasts and dropped the top beside her. She beamed with a triumphant yet bashful brace filled smile. Then she laid quickly on her side facing me to hide behind the tall grass. I don’t think I took my eyes off of her breasts since she bared them. I was fascinated.

What?, she asks embarrassed.

Your breasts have grown since the last time I saw them. Their amazing.

You think so? She responds looking down at them. They’re gonna get bigger. My Mom has big boobs. She looks down at my crotch. Oh my God! Did you get a boner from seeing these.

JoAnns breasts were fascinating. Her chest was no longer flat like mine but had 2 rounded mounds. The areola got larger and her nipples were erect. Joann asks me to lay down. As soon as I do she touches my chest. My eyes are wide open and staring at her lovely new breasts. She self consciously asks to me stop staring her boobs and to shut my eyes. I am slightly disappointed but I cooperate. I can feel her light touch as her fingers move up my arm, across my chest and down my other arm. Her touch is slow sensual. Then from my chin down the center of my chest, over my belly button to the top of my waistband. My cock involuntarily twitches inside my swim trunks from proximity of her touch. I wonder if she noticed. Her touch travels back up to my chest where it makes a lazy figure 8 around my nipples.

Your turn, I suddenly say as I sit up. Surprisingly JoAnn seems to be excited. She lays down and closes her eyes. I mimicked the path her touch took on my body. I touched her lightly as she did up her arm, across her chest above her breasts and down my other arm. Then from her chin down the center of her chest between her breasts. Over her flat belly button to the top of her bikini bottom waistband. I stopped to take a look at her camel toe. I moved my hand back up to her chest where it makes a lazy figure 8 around her the borders of her breasts.

JoAnn coos, Ooooo that feels good.

I asked her if I can touch them. She nodded approval. I cup one then the other and squeeze gently. I can’t help myself. I lean forward and take a nipple between my lips sucking and licking gently.

JoAnn smacks me on the back of my head playfully. HEY! I said you can touch but no kissing. Now you got to show me your boner.

I didn't quite understand the logic but I was willing to play along. I untied the drawstring on my swim trunks then then lifted the waistband to flash my hardened cock.

JoAnn says, I can barely see… Wait. She moves her head down placing an ear on my belly button. I can feel her naked breast against my thigh. My cock jumps. She squeals with delight. Did you just make it do that? Doesn’t it hurt being hard like that and trapped in you trunks. Maybe you should take it out.

I thought for a moment and asked, not before you show me your pussy like we used to. You show me yours and I’ll show you mine.

JoAnn responded with I don’t have anything down there. She nonchalantly pulled up the waistband of her bikini and exposed her pussy beneath the yellow material. Her thighs and torso made a Y where they met. At the Y where all creases met was a cleft barely covered by a sprinkling of dark downy hair. JoAnn pleads, come on Todd. Release it. Take your trunks off. I took my top off. I dare you.

I was never one to turn down a dare so I pulled my trunks down and my cock sprang up at full attention.

Wow! You got bigger too. JoAnn states then asks, Can I touch it?

I nod cooly, but inside I am dying for her to touch me. JoAnn touches me gently running fingers up and down the length of the shaft. I feel so good. Her touch sends shockwaves of pleasure through my body. I Instruct her to wrap her whole hand around it. She does.

Oooo. The skin is soft and warm but it’s so hard.

I ask her to move her hand up and down. She does and I moan. It feels amazing. This half naked girl is stroking my cock.

First she says, like this, while stroking. Wow I can feel the skin moving over the hard part. Then in reaction to my moan she ask, Wait….. Eww! are you getting off?

*** I crash back to the present when Elle asked if her pleasure is good. I think, did she just say pleasure? I come to my senses and reply the pressure is fine. Her skilled hands had been working on my lower back which was exposed to the top of my ass crack. I am now completely aware of my erection that has grown between me an the table.

Elle covered my back with the sheet and moved to my lower half. She exposed one leg and most of the attached buttock. While tucking the sheet between my legs, she inadvertently poked the tip of my hardened cock. It's understandable. It is typically not there. The unintentional physical attention to my cock has me wishing for more. Her hands sensually moved up and down my leg from mid thigh to ankle. If my leg could orgasm it would’ve already shot a load. It wasn’t a stretch to imagine how good those skilled hands and movement would feel on my cock. Her sexual partner was lucky. None of these thoughts helped my erection disappear. She kneaded my bare buttock then smoothed a knot in my hip. She barely gave me time to acknowledge her hands on my bare ass before putting me through the excruciating pain/pleasure of working out a knot. She covered me up and repeats on the opposite leg.

Then I began imagining what Elle looks like naked. Her breasts are C cup. Are her areola large or small? Her complexion is light so the probably pink. What does her pussy look like? She is most likely shaved clean. That seems to be what girls are doing now. Are her labia large or hidden? Her yoga pants left little to the imagination. It was perfect. Ok now I was picturing Elle naked while she massaged me.

Elle asked me how I’m doing. I know what's coming next. Shit! She needed me to turn over. I am at full mast. Hard as a rock. She lifted up the sheet and glanced away to provide a modicum of modesty. She asked me to flip over on my back and move down. I flip over hopeful that I wasn’t as hard as I thought I was. She replaced the sheet. I looked down and my hard on made a tent under the sheet. I glanced at Elles face. To credit her professionally she didn’t even seem to notice. I closed my eyes, slightly embarrassed, willing my erection soft. Nope, not gonna happen. My cock felt every movement of the sheet and loved it.

Elle was up behind my head and working. She said wow, I can feel a lot of tension in your neck and shoulders. Her hands are magic. The tension melted away. I didn’t even about sex for the moment. Until she moved her hands from the base of my neck, over my shoulders down my arms slowly and sensually. My eyes were closed but I could sense her position. I shave my head clean. I could feel what could only have been her pubic area as it lightly touching the crown of my head while she was bending forward over me. I opened my eyes and was staring at the bottom of her clothed breasts. I could only imagine her head inches from my sheet covered phallus. I wonder to myself if she is just as curious about me as I am with her.

Elle finished with my upper body. She moved the sheet to bare my leg, thigh and hip. The sheet felt exquisite as it moved against my cock as she tucked the it in under the opposite leg. The back of her hand grazed it and I nearly let out a moan. She worked my calf, then knots in my thigh when she massaged my hip. I was hyper aware of the proximity of her hands to my cock. She reached across my body and pulled my opposite hip through the sheet. The action caused her lower body to press into my naked leg. I didn’t know how much more I can take. She repeated the same work on my opposite leg. The sheet and her inadvertent touches prolonged my hardness. Before we finished she pulled on my legs to stretch them. She shook them by the ankle and left me wondering is she wanted to see my cock wiggle.

Elle announced that the massage was over by asking me how I was feeling. I told her I felt great as usual. I caught her eye before she left the room. I gave her a heartfelt apology for my condition. Sometimes it just has a mind of its own.

Elle smiled and looked down directly at the sheet where my cock was making a tent. She said flirtatiously, No worries. You’d be surprised how often that happens.
She left me to get dressed.