Random Phone Sex

I have mixed emotions about revealing parts of my past but I'm sure there are others like me.

I spent a majority of my working life in construction helping to build the city of Las Vegas also known as Sin City.

Building single family and multi family dwellings in every corner of town had its advantages developing and discovering new parts of the city. My travels for work introduced me to new to me strip clubs and adult stores not counting thrift stores along with countless street walkers ranging from trash to treasure in my travels around the City of Las Vegas.

I went through a period of time consumed with phone sex especially when I was alone cross dressing, putting on the clothes while talking with a woman added so much pleasure I began calling random phone numbers from the two inch thick Las Vegas phone book looking for women to talk with for as long as I could keep them on the phone while I pleasured myself talking about women's clothing.

The amount of lonely, bored, curious women I talked with is crazy as I think back on it a number in the hundreds or thousands.

My normal introduction upon hearing a woman answer when I dialed a random number went something like this.

"Hi, would you mind talking with me for a few minutes... I don't know you but I don't have anyone I can talk to about dressing up... Ok?" I would ask in a soft harmless tone of voice which would either be a quick hangup or she would agree to talk with me usually asking why I called.

" I just... I just don't have anyone that I can talk to about dressing up in women's clothes." I would reply hoping for a little sympathy and understanding mixed with curiosity.

"You like wearing women's clothes?" she'd asks me opening the door for me to go further as my dick swelled even harder.

At this point I know I have them for a little longer I've caught her interest and she has accepted the conversation giving me permission to continue.

"Yes.... I like dressing up in some stuff... I'm dressed up now... can I tell you what I have on? I ask her as my dick swells.

If she hasn't hung up the phone by now I have her curiosity and the call might be worth it, if she hangs up then I just dialed another number repeating my same lines until I find a woman who agrees to talk with me.

"Sure... tell me what you're wearing." she says while settling down for a conversation.

Now the fun for me begins and I do my best to keep her interested while I do my thing, slowly working myself to orgasm during our talk.

"Oh thank you.... are you sure you don't mind? I say again just to reassure that she is ok with us talking.

"Tell me.... now I'm curious.... what are you wearing?" she asked again which is when I go for it.

"I'm wearing a black bra that I have filled out with waded up pantyhose, then I have on a black garter belt with these black stockings that go up to the top of my leg that I attached to the garters that looks really sexy... over that I have on a black sexy nightgown that just hangs down past the garters and a pair of 4" inch high heels." I tell her waiting for her response even though she has been making little comments the entire time.

"Sounds sexy." she says.

"I bet you look nice.... your outfit sounds nice." she adds.

"Do you like dressing up in lingerie?" I instantly asked her.

"Wearing high heels?" I add in an attempt to get her to talk about her clothes too.

This changed from woman to woman, some owning similar outfits to what I described others saying that they haven't in years, others wanting to buy something similar but haven't.

Each woman being different adds to the excitement, how far can I take them added to the adventure.

The more comfortable I can make them in our conversation the more they will open up.

"Why are you wearing women's clothes... you're a guy right? they always ask.

"Because they look so sexy and they feel really good on." I answer.

"So when did you start wearing women's clothes?" they also asked which makes for a much better conversation when they ask more and more questions.

"Do you like guys or girls?" is another common question that they would ask as their curiosity builds.

"I love women.... but when I dress up in women's things I like to play the role of a woman and get with guys but I have to be dressed up." when I tell them that it opens a flood of interest and questions. I can hear them change interest towards sex with more excitement in their voice more curiosity.

"What are you wearing?" I ask them now that I've got their full attention trying to get her to relax a little more.

Nothing special was the most common answer making me work for what I was after, having to pry it out of some while others were easy.

Depending on the time of year it was mostly shorts and a top or sweats making me ask about their bra and panties. Shorts with no panties was good because I could get them to finger their pussy without taking the shorts off, tops without a bra were fun to because I would get them to pinch their nipples during our conversation.

On a couple occasions I've talked them into changing into some of their sexy lingerie things that they have or a little nightgown describing everything to me, asking them how sexy they look in their clothes while reminding them how sexy I looked removing even more of their guard.

The women who changed their clothes during our conversation I've always gotten them to play with themselves making them cum during our talk only makes me call them again usually within a few days so we can talk each other off again not wanting to much time to pass.

I've talked with women just getting home from work, others getting ready to go to work, I've even called businesses like 24 hour cleaners knowing that they would most likely be sitting around bored and they were a lot of fun too.

I found that a majority of the women at home were married and had been for some time with busy husbands and kids with no time for sex so talking to a voice on the phone when they were alone in an empty house was exciting for them to.

With Vegas being a 24 hour town I also found women to talk with at night while the husband was at work the kids asleep. Horny faithful wives left to sleep alone with their vibrators close by already half naked and in bed when the phone rings, they often agreed to talk with me.

Always starting my conversations the same way asking to talk about women's clothing mostly lingerie, stockings and heels usually got their initial interest, once I told them everything that I was wearing they would start asking questions which I was more than happy to answer.

When they would asked me if I liked girls or guys I'd always answer the same way.

I like girls.... but if I'm dressed up in ladies lingerie then I can get with guys but only to play the role of a woman. That answer would always increase their interest with even more questions.

"So you have been with a man.... had sex with him?" she ask with interest and excitement.

When I hear the excitement in her voice asking that question I will make a move to increase the conversation a little.

"Can I tell you what I have on?" I ask.

"Sure tell me." she answered.

"Are you sure you don't mind?" I followed up with.

"Tell me what you're wearing." she says clearly asking me what I'm wearing relieving some fear in case the phone is tapped.

This is the moment I was hoping for when I first called this phone number, to have a conversation with a woman about crossdressing my crossdressing.

Let the fun begin.

"Well I have on a pair of tan pantyhose that I cut the panel out of to make them crotchless, then I have on a black one piece that snaps at the crotch, a black garter belt and black thigh high stockings, over that I have a black silky nightgown that goes just past my butt." I tell her as I gently rub my fingers over the outline of my dick restricted by the sexy lingerie.

"Sounds sexy." she says.

"You don't need to wear pantyhose with stockings." she tells me.

"I don't want to shave my legs so I wear pantyhose to hide my leg hair." I replied to explain why I was wearing both.

"Well it sounds like you look really nice... do you like the way the clothes feel?" she asks.

"I love the way everything feels against my skin... it looks really good to when I have heels on." I answer.

"You have heels on?... you didn't tell me that you had heels on too." she says.

"Sorry... yes I have a pair of high heels on. Do you like wearing heels?" I ask to move our conversation toward her.

"I'm a girl of course I wear heels!" she answered.

"What size do you wear?" I quickly asked another question.

"Size 8!" she replied.

"No... I mean how high?" I asked even though I did want to know her shoe size because if she a close to a size that fits me I would push towards getting one of her old pair which I have done a couple dozen times. I've even had these women donate clothes to me for me to wear when I dress up.

We spend time talking about heel height and types as we develop a momentary friendship.

"Do you have any garter belts or sexy lingerie like I'm wearing?" I ask.

"I have a few things but it's been years since I have worn them." she answers.

"Like what?" I followed.

"Well we have been married fourteen years and I wear a new outfit on our anniversary so I have a drawer full." she said with a little laughter.

"Too bad that's the only night we have sex!" she says sarcastically but maybe not.

"So you like dressing up in sexy lingerie for your husband?" I ask her.

"Yes of course... don't you? she asks me.

"It's the only way I can get with a guy... I have to be dressed up or I can't do it." I tell her.

"What do you do when you're with a man? Do you kiss?" she asked.

"Oh no I don't kiss guys but I do like kissing girls." I replied.

"When I get with a guy it's strictly for sex." I tell her which causes her to gasp lightly.

"So what.... you just give them a blowjob?" she asked me.

"Oh yeah I like sucking a dick when I'm all dressed up like I am now." I openly tell her able to since her curiosity building.

"Is that all you do?" she asks as I think to myself that this will be a good call.

"No." I reply.

"Sometimes they screw me." I tell her waiting to hear her response.

"They fuck you in the ass?" she asked loudly.

"You like that?" she followed

"So this is what you wear when you get with a man... what you're wearing now?" she added.

"Well when I dress up like a woman I want to play the role of a woman. Sucking their dick and letting them screw my ass are the only two things that we can experience that feel the same." I replied with my explanation for wanting to do it.

"What are you wearing?" I ask.

"Nothing now!" she replies.

"Are you wet?" I ask now that I know this woman is naked and hasn't hung up.

"Yes!" she answers.

"Thinking about you a guy dressing up in lingerie to suck guys off, even letting them fuck your ass has made me wet. I can't stop rubbing myself." she tells me.

I get the feeling that it's been a while since she has had any sex and that I have lit the fuse.

"Have you had anal sex?" I asked knowing that she was rubbing her clit.

"Yes a few times when my husband just wouldn't stop asking... but it hurts." she says.

"Why.... is his dick big?" I ask waiting to hear her answer.

"He's about seven inches long but it hurts so he's never got the whole thing in." she replied.

"How big have you had?" she asked.

I couldn't wait to answer her question because I knew she would have more questions after.

"The biggest man so far was ten and a half inches but I have a couple toys bigger than that." I tell her knowing that I just made her even wetter.

"You have toys?" she asked in curiosity.

"What kind of toys do you mean?" she quickly followed up with.

"When I dress up I don't always look for guys, I play with dildos that look just like a dick." I tell her.

"I like the way it feels.... I'm using one right now." I say to her knowing that my words are getting her excited.

"You're fucking yourself right now?" she asks with excitement.

"Yes.... please don't be mad!" I answer.

"What are you doing?" she asked now sounding like she wants all the details.

"I'm on the floor in my bedroom on my knees pretty much sitting on my high heels, then I have this black dildo that looks just like a real dick that's twelve inches long and kinda fat that I've been riding up and down on while we're talking."

"Does it feel good?" she asked in a more subdued tone.

"Oh yes it feels really good sliding in and out of me especially when I go deeper." I answered.

"The feeling of it in my ass makes my cock so hard." I tell her.

"What are you doing?" I ask her.

"Just rubbing my pussy listening to you... thinking about what you are doing right now." she says sounding like she has laid down to play with herself.

"Do you have any toys?" I ask.

"Yes... but I don't need them right now.... maybe next time."she answered also throwing me for a loop about the possibility of a next time, another conversation.

I start to moan a bit enjoying the direction of our conversation as I continue my slow rhythmic motion moving my ass up down and side to side on half of the dildo as I sit on my heels with the stiletto tips poking into my skin, my rock hard cock trapped under layers of silky material and nylon.

"Sounds like you are enjoying yourself." she said hearing the sounds of my pleasure.

"I am thanks to you! I'm happy you're talking with me." I tell her.

"No problem... I'm kind of glad you called." she says.

"What are you doing right now?" I ask her with a good idea already.

"I'm rubbing myself." she answers.

"I'm so wet." she adds.

"Slide a finger inside you." I tell her.

"Let me hear how wet you are!" I add telling her to put the phone down by her pussy so that I can hear her fingering herself. I can hear her fingers squishing around between her juicy pussy lips sounding like a finger in a melon.

She was soaking wet from our open conversation and I was having a hard time not releasing my cock to stroke it but I know as soon as I do I'm cuming.

"Are your nipples hard?" I ask about her boobs for the first time.

"Like big pencil erasers." she answered. quickly,

"But I have small tits." she adds.

"What size bra do you wear?" I ask since we are talking about her boobs.

"I don't wear them often but when I do a 34B." she says.

"They sound perfect." I tell her.

""Are you still riding your toy?" she asks me.

"Oh yes.... it feels so good... I just want to go deeper." I answered.

"Then go deeper..... are you stroking yourself?" she asked, almost taking turns in our questioning.

"No... if I was to touch my dick right now I'd cum."

"You've had your dick trapped under all of those clothes this entire time." she asks.

"Yes.... because I like talking to you... I just wanted to enjoy as much of this as I could." I tell her.

"I want you to cum... you can call me tomorrow night or any night Monday thru Thursday because that's when he works.... my husband." she tells me.

Hearing her say that, that she wants me to call her again tomorrow night for more phone sex was a gift.

"Get your dick out and sit down on that dick so I can hear you cum and I will cum again too." she says admitting that she has already gotten off once while we were talking.

"I want to hear you sit down taking all of that dick in your ass and jackoff!" she says with more authority.

I reached underneath me between my legs unsnapping the clasp holding the one piece together, my cock smashed under the pantyhose the area around my mushroom head wet from precum.

"Are you doing it?" she asked.

"Almost... my cock is still smashed under the pantyhose." I answered.

"Rip them open!... Grab your cock!.... Sit your ass on the floor shoving that dildo all the way in your ass.... and CUM!!" she ordered me introducing me to another side of her.

I did exactly as ordered ripping my pantyhose open with a tug where I cut the panel out, my cock jumping straight out finally freed from its confinement as I moved my feet from supporting my ass to sit taking the black twelve inch dildo deep inside my hole causing me to let out a loud moan of pleasure.

"You have that dick deep inside you... Now CUM.... CUM FOR ME," she tells me as I grip my dick shooting cum at least three feet as I moaned and groan loudly for her benefit as I hear her cuming as well right along with me.

After a short silence in conversation while we both catch our breath recovering from our intense orgasms she was the first to speak.

"Are you ok?" she asked.

"That was intense... I never thought phone sex could be so satisfying but wow... that was incredible. Sounds to me that you really enjoyed sitting down on your toy.... I can't believe it doesn't hurt and it sounds big.... to big for me!" she added.

"I have bigger!" I replied.

"But it felt great thanks to you. Talking to you made everything even better. Thank you!" I tell her knowing our fun was about to end.

"You have bigger toys than that.... really! Doesn't it hurt... I couldn't do it." she said.

"No... maybe at first but it feels great. I can get off without touching my dick... just riding a dildo can make me cum which is why I have so many toys because I start small and work up in size." I tell her.

"How interesting. When you called me did you think I would talk or hang up?" she asked.

"I didn't know but I was really hoping that you would talk when I heard the sound of your voice." I replied.

"So you just got all dressed up in women's clothing and call random women just to find one to talk with while you jackoff." When she said that I began to feel bad even a bit embarrassed.

"Well you called the right person.... talking with you I came twice and that hasn't happened in years. I enjoy hearing how nasty you are and wouldn't mind if you called me again tomorrow night at the same time." she openly admitted inviting me to call her again tomorrow.

"I will even wear something sexy for you." she tells me.

"I can't wait.... we will have fun and you can pick out the toy you want me to use." I respond to her with excitement.

"Now go get cleaned up and call me tomorrow." she says ending our conversation for the night. I thanked her again letting her know that I would be calling her tomorrow wishing her a good night.

to be continued...