Adventures with Julie

Adventures with Julie

I don't recall what prompted me to make the initial telephone contact with Julie. I'm sure it was related to my quest for erotic pleasure---that's just my style. Nonetheless, whatever that first call was about, it blossomed into a truly exciting, long-term phone-sex relationship. She and I would talk on the phone periodically over many months, spanning about a year or maybe more. I, of course, always initiated the phone calls because she did not have my phone number; and she seemed to be quite content with that. Some women have fussed over the fact that they could not call me whenever they felt like being a bit sexual; but most women, including Julie, did not push the issue recognizing that I must have had some reason to keep my practice secret.

These "periodic calls" would be about weekly for most women. Sometimes, when the woman and I were on a relatively "hot streak" of erotic conversation, the frequency increase to about daily for a number of days. More often, however, I would allow a week or two between phone calls. One reason for this longer frequency was the large number of women in my "calling queue". I could not spare the time away from my (non-sexual) professional activities to phone all of these women every day. I frequently had between 30 and 50 women who might have anticipated a phone call from their "telephone sex partner" at about any time. Naturally, not every woman realized that they held that title; some just thought that they were being a friend to a polite cross-dressing gentleman. Julie seemed to be comfortable with me calling about once a week and with not being able to call me.

Over the year or more that she and I enjoyed phone sex, we naturally learned quite a bit about one another. Julie learned about me that I was an intelligent and considerate cross dresser with a very forward and creative approach to sexuality. She learned that I was considerably older that she, that I loved to masturbate, and that I was very open and honest about my penchant for erotic sex. I learned much about her as well:

She was a married woman in her early 30s.
I think I recall that she had one or two children of school age (I'd call while they were gone).
She had been caught by her husband cheating on him with another lover once.
They had reconciled but it was a shaky reconciliation; he remained suspicious.
She did share with me her last name (not revealed here) and a mailing address so I could send her sexual things.
She did smoke marijuana when she was alone (I think it was a problem for her.)
She liked to read paperback sex books for erotic arousal (this was prior to the availability of internet sexual material).
She liked to dress sexy to turn her husband on.
She really loved receiving oral sex
I found out---part way through our phone sex relationship---that she, too, enjoyed masturbation

Our Phone Calls:

A few special highlights of our year's worth of phone sex stand out in my mind. Well into our periodic phone sex sessions, I knew that Julie was well-aware of the fact that I would masturbate whenever we chatted. She seemed truly accepting of that and maybe even a little aroused by it. One one occasion, I mentioned to Julie that I would find it especially satisfying if she would join me in masturbating while we talked. Now, Julie had a friendly, happy speaking voice. At times she even giggled as we talked. When I mentioned my desire to have her share in the sex of the moment by masturbating with me, Julie responded: "Oh you silly man. Aren't you listening? Don't you realize that whenever I am giggling, I am masturbating. I always giggle when I masturbate!" Basically, Julie was telling me she was then and had always been masturbating during most of our phone sex conversations.

On another occasion, Julie and I were chatting about oral sex. She confessed to me that she dearly loved receiving oral sex. She loved having a man's face buried between her more-than-willing spread legs. Oh, she would do oral sex on her partner if requested; it did not bother her at all. But (and her voice oozed sensuality as she said this) she delighted above all if having a man licking her pussy. Julie confessed to me once: "I really think that if, for some reason, I should find out that I could never again receive oral sex, I would rather die!" That was the most extreme proclamation I have ever heard. Now, I love performing oral sex on a woman---but not to die for!

Julie did enjoy her marijuana. I think that may have been a little bit of a problem for her. One time that I called, her voice was somehow different, her speech patterns not quite the same, and her interest in talking to me clearly diminished. She was, at the moment, embroiled in the euphoria of her drug of choice. She recognized my voice and knew my desire and my intent; but Julie said: "Not now. I don't want to spoil the moment. Call me another time." I did not push the issue and, indeed, called her several other times.

Julie and I did meet face to face on one occasion; and that exciting interaction is the main thrust of this chapter. I have one more tale, however, to share with you stemming from a phone conversation before detailing that afternoon.

I must explain an aside first. My philosophy of life in response to "hard days at the office" is not like many other people's responses. Most people will stop into a bar on the way home and slam down a few drinks to soften the edge left by the day's troubles. I find that sort of self-abuse non-productive and never helpful to me in any way; so I never did it. Instead, I choose to go shopping for pretty lingerie. On a sort-of-bad day, I might stop in and purchase a pretty bra. On a really pretty bad day, that purchase might extend to a complete bra and panty set. On a "pisser" of a day where nothing went right, I would go all out buying a new matching bra and panty set, a pair of sexy thigh high hose, and a slinky sexy negligee. I wouldn't ever even think of the worries of the day once I returned home and donned these sexy items!

On one of these solo shopping ventures following a hectic day at the office, I entered a woman's lingerie shop at which I had shopped occasionally before. In fact, I knew one of the older clerks (maybe in her 40s) to be especially helpful. Her name is no longer recalled; but she knew of my love of wearing women's clothing and seemed always eager to help me. Upon entering the store, she spotted me and hurried to intersect me.

"Oh, so good to see you!" she exclaimed clearly quite earnest in her zeal. Placing her hand softly on my arm, she explained a bit further: "We recently got in a shipment of really cute bra-and-panty sets. I saw this one set and thought of you right away! I think you'll love it. Both the bra and the panty are gold lemay fabric with that characteristic shimmering metallic-like reflection. And the edges of both pieces are edged in black fur-like beading. I set aside a pair in the back room that are just your size." Then, realizing that it would be inappropriate to require me to buy her selection, she added apologetically: "You don't have to buy them if you don't like the set. I can put them back out on the floor."

In truth, they were every bit as exciting and sexy as she made them out to be. I not only gladly bought the set she had set aside for me; but I bought another pair for Julie in her sizes. I phoned Julie a few days later and asked her permission to send her a "sexy gift" of clothing. I told her it would be a bra and panty set but said no more about it. She agreed that I could send it; and we decided she would tell her husband that "she had bought the set to turn him on when she first wore them for his sexual stimulation!" Together, we worked out a mailing schedule so the mail would arrive during the normal work week such that her husband would never know of the delivery. Faithful to her request, I mailed the package and allowed a couple weeks to pass before calling again. (This is the end of the earlier aside.)

Julie was all excited when she heard my voice. She bubbled over as she thanked me over and over again. The gift was a very welcome surprise; and the sexual aspect of it worked wonderfully. Her husband was so happy that "she had bought such a set of lingerie just to enhance their intimate sex". Julie went on to add that one day, a couple days following receipt of the package, she and her husband went to a dark and smoky bar just for late evening drinks. She wore the bra as an outer garment feigning any other covering on her top. She also told me she wore a very short white skirt that only came to the middle of her thighs; and she chose to omit any underwear! She was naked under her skirt. Julie and her husband found a vacant end of the bar (no one else was anywhere near that end of the bar), and they intentionally started to "make out". Others in the smoky room gave them plenty of space to let them have---what appeared to everyone else---a kissing session. In reality, Julie allowed her husband to surreptitiously feel her up; and she managed to work the zipper on his pants down. By prior arrangement, he had also not worn any underpants. Julie was overjoyed to report that her husband actually finger fucked her right there at the end of the bar in this dark and smoky tavern. She shared how exciting it was to be doing this with the slender possibility of getting caught. I was masturbating furiously as she described this event with her husband. I hope she was as well as she told me the story.

That's the kind of woman Julie was---free spirited, willing to take controlled risks, almost as creatively erotic as I am.

An Erotic Afternoon:

I mentioned earlier that Julie and I did meet face to face on one occasion. This happened several months into our friendship. I was curious about her and what she looked like and how she'd respond to me. Similarly, she was just as curious about me and what I looked like and what my sexual approach might be when actually sitting next to her. We chose to meet in the middle of a week in early February. The "date" was to consist of "drinks" in the lounge area of an upper middle-class restaurant. The meeting time was set for 2 PM.

I arrived at just about exactly on time. The Greeter/Hostess at the door responded to my comment about "meeting a young lady for drinks at 2 PM" by pointing out the only other person in the lounge. She was already seated in an upholstered semi-circular booth at the far end of the lounge. The Hostess guided me to her table and we greeted one another as though we were long-separated friends. The Hostess left, I settled in the seat as we nervously introduced ourselves. In a moment, the sex began.

Julie wore a very loose knit black sweater only slightly covering her black silky satin bra. Her jet black hair framed an attractive very white face with bright enticing eyes. Her whole countenance sparked with the same energy I had sensed over the telephone. Her hair mingled with the fabric of her sweater at her shoulders presenting a nice black-on-black combination of differing textures. I think she wore a black skirt as well; but I cannot recall this detail. The table was a semi-circle with rounded corners. It fit the half-circular curved seat of our private booth nicely leaving ample room to sit either facing the table or facing one another with opposite arms supported by the back of the cushioned seat. I sat at the back of the half circle twisted to face her; and Julie sat to my right---also facing me. We were close enough to talk quietly. Such conversations as we were about to have should not be overheard.

A Server came to our table to inquire about drinks. The two of us opted for a bottle of champagne which soon arrived with a pair of tall fluted glasses. The Server was advised that we had much to chat about; and he need not bother us with frequent appearances. Given that setting, we were alone. The sexual conversation could begin.

I had opted to bring Julie a few small gifts. I genuinely enjoy giving a woman known to me for only a few moments a gift of something sensual---even sexual. I enjoy flaunting what is considered "appropriate" with what many people wish they could have done. My first gift was a pair of silky French cut bikini panties in her size. The panties were white in color with a number of playful red hearts printed all over the almost translucent fabric. Concerned over what to tell her husband, I freed her to lie to him telling him that "she bought the panties as a Valentine's Day present for him to enjoy". After all, it was early February, and that lie made perfect sense. The second gift to Julie was a paperback book of pornography. As I gave it to her, I squeezed her hand a little and said: "This is for you to enjoy while masturbating. I ask you to finger fuck yourself as you read this book." She smiled to me and nodded an affirmation. The final gift was a small can of whipping cream dessert topping. This gift was to be used on her pussy while lying on her back on a bed with her legs extended into the air. The intention was for her to use this while her husband was performing oral sex on her.

I don't recall what we talked about that afternoon. I know it was wonderfully erotic. I know I enjoyed an erection from almost the moment I sat down with Julie. I do recall complimenting her on the very sexy sweater she was wearing. I openly pointed out what most men would observe but refrain from saying: that her pretty bra was both very visible and quite a sexual turn on for me as I could see it through the loose knit fabric. I freely asked Julie the first on many 'forward' questions of that afternoon. As we sat there sipping our champagne, I simply asked her to please lift her sweater to permit me a better view of her sexy bra. Although she did check the location of lounge employees to make sure they were elsewhere and not focused in our direction, Julie freely and willingly lifted the right side of her sweater to give me a completely unhindered view of her bra. The shiny black was overlaid with a repeated pattern of of a second density black fabric. A few seconds later, Julie lowered her sweater not wanting to risk detection.

A couple hours into our champagne conversation, our Server returned and we ordered a second bottle of the bubbly. After he left, I decided to ask Julie a question to which I fully expected a negative response. I began: "Julie, this has been a stimulating afternoon. I think you know that. I am enjoying a rock hard hard on just being here with you. I am going to ask you a question to which you should feel very free to decline if you so desire. I know that you really love to have a man performing oral sex on you. At the same time, I know I am very skilled at pleasuring a woman's pussy with my tongue, mouth and my whole face. Julie, would you consider allowing me to take you from this lounge to a nearby motel where I would be very happy to lick your pussy to several repeated orgasms?"

Julie had actually anticipated such a proposal and offered the following well-rehearsed reply: "Thank you for the offer. I kind of thought you might ask something like that. I confess I am sorely tempted. I know I would love that at this moment. But, as you already know, I have already been caught cheating on my husband once before. I cannot risk getting caught again. As much as I want to say 'yes'; I'm afraid I am going to say 'no'". I was well prepared for that rejection. I expected it; but, still, I was disappointed.

Shortly thereafter, Julie asked to be excused because she needed to visit the ladies bathroom. The effects of two or three bottles of champagne were taking its toll. Before she slid across the leather seat to exit the booth, I asked her one more question: "Julie, do your panties match the pretty bra you are wearing?" She smiled and her head nodded the affirmative. I continued: "Could I ask you to take your panties off while you are in the restroom and not put them back on? I'd like to see them and feel them. Please bring them out for me to see. Would you do that?" Julie smiled again without answering; but I had my hopes up---along with my penis.

She was gone a bit longer than necessary to just pee. Many years later, my reflection on that moment causes me to wonder if Julie had used that opportunity for a quick masturbation. If that had been the case, I wish she would have told me so. I would have rejoiced with her for doing that! Nonetheless, she did return and resumed her same seat prepared to move on to the next sexual discussion topic. Then, without saying a word, Julie removed from her purse a small handful of shiny black fabric with the same black pattern as her bra repeated on the material. She placed her panties on the continuous curved seat cushion between us. Her eyes were filled with sexual lust as she watched me pick up the panties and feel the erotic material. I looked right into her eyes as I surrepticiously brushed the wispy wad of sensual fabric against my left cheek allowing the trailing motion to draw the fabric right under my nose. It was a quietly erotic moment.

The next adventure for the afternoon, fueled by the sight, feel, and smell of Julie's sexy black panties, began with another audacious question: "Julie, I am pretty turned on at the moment. I hope and believe that you are as well." Her smile answered that question. "We are all alone in this lounge and have been all afternoon long. We are a long way from the bartender; and you can watch over my right shoulder for the possible approach of our Server. I'd like to expose myself to you right here and now. Would that be ok? Then I'd like to jack off for you as well. Would you like to see that?"

Julie's eyes quickly surveyed the vicinity to ensure my assessment of employee locations had been accurate. Then her eyes returned to me as she nodded another affirmation. Nervously, I raised my left leg, now bent at the knee, so it rested on the seat cushion between us. This spread my legs amply. My hand found the tab to my zipper; and Julie's gaze followed my hand as it slowly drew down the zipper. A few seconds of fumbling about brought into view my stiff cock. Julie looked at the shiny head quivering before her eyes. The excitement was fueled by the potential risk involved. Julie noted details: she commented on its slightly reddish color, the slight curvature to my right which I explained was the result of many years of masturbation, and how exciting the moment was for her. For our protection, she made frequent furtive glances around our immediate surroundings. Secure that she would safeguard both of us from unwanted detection, I began to stroke the long sensitive flesh that projected proudly from my trousers. How exciting it was for me to be masturbating in a public place with a willing and lustful partner greedily watching every stroke---how the skin bunched up above my fist on the upstroke and how it stretched thin over the throbbing shaft on the down stroke. At one point, Julie advised me to try to control my shoulder motion a bit more so---if someone were to glance our way---they would not see the telltale movement of my shoulder. As the time for an eruption drew near, Julie held her black panties in her spread hands eagerly anticipating the sight about to unfold. I controlled my groans of ecstasy and pleasure by swallowing them and whispered softly that she should be ready soon!

My cum spurted in several droplets onto the fabric destined to receive it. The sight of the pearly iridescence spotted on the shiny black fabric was nearly overwhelming. Humorously, one thick gob of cum flew uncontrollably over the top of the fabric and landed right on Julie's left inside forearm. I quickly grunted a soft apology; but she lustfully dismissed the incident as no problem at all. The entire event ended in just a few moments. I wiped the last drops oozing from my cock onto the panties. I asked her what we should do with the soiled panties; and Julie only smiled as she wadded them into a tight bunch and placed them back into her purse.

The next hour or so saw additional people entering the lounge area---each with their own social agenda. Whatever it may have been, I am sure Julie and I both believed that same scene was not likely to be re-enacted by another couple that night. The time approached 6:00 PM and Julie explained that she needed to go pick up her husband from work. She didn't want to be late lest he question where she had been and, thus, her faithfulness.

I walked her to her car. We softly thanked one another and issued a gentle parting smile for the other. I asked one last favor of her and was granted that wish. I placed my hand outside her clothing against her pussy mound and "felt her up". I promised her that I would think of that final act of the afternoon/evening as I jacked off for her in bed that night. We kissed warmly and deeply as lovers destined never again to see one another. She entered her car, closed the door, and left.

That Same Evening:

I drove west along one of our city's major routes reveling in the lingering splendor of the afternoon's 4 hours worth of sexual activity. A woman standing at a scheduled bus stop was, for some reason, "thumbing a ride". Thinking she might need a ride more quickly than the next bus, I pulled to the curb and watched her scurry toward my waiting car. I assessed the woman to be in her early to middle 40s. She was not unattractive; but neither was she a "knockout". Fastening her seatbelt, she uttered a quick explanation of why she was hitching a ride although I don't, at this time, recall it. She then continued with the perfunctory: "How are you today?"

"Fine." was my equally tasteless response. She chattered on a bit about mundane matters; but my mind was rebelling at my own immediate response. With a little risk, I continued: "Well, maybe not so 'fine'. I just came from a lounge where I had drinks with a lovely younger woman for four hours. I had hoped that the afternoon might evolve into a sexual adventure at a nearby motel; but it didn't happen. So, I guess I am less than 'fine'."

The woman's response was sympathetic. Either she did not want to appear shocked at my sexual openness or she truly understood my disappointment. Her response went something like: "Oh, that's too bad. I'm sorry to hear that. You must be pretty disappointed." Her words carried no hint of which direction she may be thinking.

We both returned to her mindless chit-chat---none of which I paid much attention to. My mind was still whirling. I realized that even though Julie had not elected to go to a motel with me, I did jack off in a public place with her watching. That was pretty exciting! So, I again reversed and refined my initial response to her saying: "Come to think of it more deeply, maybe the afternoon was a bit better than I led you to believe. True, the woman declined to go to a motel with me; but our conversation was very erotic. In fact ..." I hesitated a few seconds. "In fact, I did receive her permission to masturbate for her pleasure right there in the lounge. She watched me through the whole process. It was pretty intense!" I waited for whatever response she might issue unsure of what that might be.

"Oh, wow, that's pretty cool. Impressive. Glad you got some satisfaction out of the afternoon." I was pleased that she was not pissed at my openness; and, yet, she eventually returned to her unlistened-to banter.

A few minutes further down the boulevard, my next words were forming in my mind. Before speaking them and with no prior explanation to her, I guided my car to an open parking spot along the street, turned the engine off, removed the keys and placed them on the dash board.

"What are you doing?" she inquired with some slight emotion. "Why did you stop?"

Not answering her direct question, I said: "I want to ask you a question; but I want you to feel secure that if my question troubles you, you have every opportunity to easily exit my car. Please check your door to see that it is unlocked." Her face was puzzled but she checked the door as requested. Her eyes asked me to ask the question. She was curious.

"I'd like to take you to a motel and have sex with you. I know that is forward of me. You can say 'no' and I'll still take you where you want to go with no risk to your person; or you can choose to exit the car here."

The woman thought a moment. I was nervous. I think she was too. Then she uttered softly: "OK. Yes, I'll go with you."

Continuing driving west, our search was no longer for her initial destination but for a suitable motel. One was found in just a few moments. She remained in the car while I paid for the room and some fictitious person was registered for the night. We closed and locked the door behind us. I confess that this was a surprise conclusion to an exciting day that even I could not have predicted beforehand. Awkwardly, we fumbled with one another's clothing. We were laying on the bed when it was my turn to remove her pantyhose. That experience, alone, taught me how much I hate pantyhose. Removing them from a woman can actually take away a man's immediate sex drive and lessen the lust for what is to follow. It takes half a minute to work the elastic waist band down; and they always come off inside out.

We both enjoyed pleasurable orgasms---not earth shaking, but surely better than a toothache. After sex, we lay back on the bed---she cuddled in my left arm. She reviewed the last couple hours aloud and inquired a bit more about me and my adventurous outlook on sex. I told her freely and proudly of my wonderful sexual experiences and activities with dozens of woman. I explained that most of the time, I merely masturbate while helping a woman plot and plan erotic and creative sex with the partner of her own choosing. I could tell the woman was beginning to doubt my veracity.

In time, she said a softly spoken "YaYa, sure. You can tell me anything."

I was just a little annoyed to be questioned about my honesty. I asked her to hand me the telephone on the nightstand next to the bed. I told her that I was going to phone one or two of my current "regular" phone sex partners. I further told her what activities each of them and I had done even including phrases we might have used with one another. I only knew two or three phone numbers by heart, so I was a bit limited. No one was home at the first number dialed; so that did nothing to prove my point. Nikki did answer her phone, however. I explained to her that I had just met a woman at a street corner, given her a lift, engaged her in progressively sexual conversation, and then politely asked her if she might like to fuck. I explained further that we found a motel and had just had an hour's sex and that, afterward, the woman questions my sexual proclivity. I assured Nikki that I had dialed her phone number protecting that number from being seen; and I ended my conversation with her by telling her just a little about my conversation with the woman about my activities with Nikki. I asked Nikki to talk to the woman: "Nikki, will you chat with my sex partner of the evening and answer her questions?"

The two talked for five minutes and the woman's eyes widened in disbelief as Nikki confirmed every detail of my revelation.

I asked the woman for her phone number and/or address in case she might care to carry on further sexual adventures. She appeared willing and anxious to do this and wrote down both a home address and a telephone number. We dressed and I took her a couple more miles to a street corner she had identified (not the original location mentioned when she entered the car).

Subsequently, I checked the street address she had given me only to learn that no such number existed. The telephone number was, likewise, bogus. I never did learn her name. I never saw her again. She was a sexual wisp-of-the-wind. A one-night stand.

Julie and I continued phone sex for several additional months; but she confessed that she feared what she might agree to if we met again face to face. Eventually, her husband left her (divorce) again and she was not associated any longer with the only phone number I had for her.