Double or Nothing?

A little bit of background may be helpful, since this may sound a bit unusual.

I have had a fantasy for as long as I can remember about being teased to the point of blue balls by a beautiful woman, then denied. I've tried phone sex, but it's pretty hit and miss with whether the woman understands the concept - they seem to get a bit confused about wanting not to come, or leaving the decision up to her and really wanting her to end the call without a climax. Of course, sometimes she'd have to let me come, or it wouldn't be a tease – so, it gets a bit involved for a woman to understand, if she hasn't heard about this type of thing before.

Well, I was checking out the erotic services section of a web listing agency one day when I came across a listing for an escort named Ashley. She was really cute, and the ad linked to her website. There were a bunch of pictures of her, again all very attractive. What sort of caught my eye in particular, in addition to her looks, was the inclusion of the fact that she listed as additional services "fantasy roleplay" and "mild domination". I knew I wasn't into "domination" per se, and the way her ad was worded, it didn't sound like she was, either. But, it definitely sounded like she might be open to what I had in mind.

Well, the ad said to call about availability and rates. What could it hurt to call – maybe I'd be able to tell something from hearing her voice. Experience told me she wouldn't be willing to get into a lot of detail over the phone. Women in that business are pretty used to guys trying to get them to engage in explicit descriptions of their services over the phone, then jacking off. Saves the jerk a lot of money, and irritates the woman considerably. But I thought hearing her voice would help me decide whether to proceed further.

"Hello," came the voice when I called Ashley's number. I had actually been very nervous about calling, probably because I knew I really wanted to try this. To work up my "nerve", I had printed some of my favorite sexy pictures from the web. They were lying next to me on the bed, and I was completely nude. Since I hadn't come in 24 days, I had gotten pretty hard while gazing at the pictures and very lightly stroking my cock. My hard cock provided me the motivation I needed to go ahead and make the call. (Now do you understand why these gals are somewhat suspicious when a guy calls with a lot of questions?)

Her voice sounded very sexy – a nice clear voice, calm and confident in herself. Not rushed.

I was able to sound very calm myself, introducing myself, complimenting her website, and then inquiring about rates and availability. She gave me the basic information, and told me we could discuss specific expectations in person. Then she asked if I was interested in an appointment. I blurted out that I would like to see her the next afternoon for two hours. She said, "That's great, Pete, I have an opening at 2PM," and she gave me directions to her place.

I hung up the phone, took a deep breath, and thought about what I'd done. I noticed that my cock was rigid, almost to the point of trembling. I stroked it a little, then decided not to get close enough to the edge to have an accident before my visit to see Ashley.

What I'd decided to ask for is the following:

We would be together for two hours (paid in advance - the normal protocol). I would be completely nude, and she would massage my groin (cock and balls). We would have a clock in the room, visible only to her. She would be trying her best to make me want to come. If she could make me ask her to make me come, I would automatically have to pay her double for the session. In other words, the amount she was paid in advance would be matched by me if I asked her to make me come before the two hours had expired.

On the other hand, if I never asked to come, she would continue to massage my groin for the entire two hours, and I would simply try my best to come (if she were very skillful, I would not be able to). But, she would have to get me very close to the edge, in order to induce me to ask to come, because that way she doubles her money for the session.

If I do ask to come, and pay her the additional cash, she will continue to tease and massage my cock and balls. It will be completely up to her at that point whether or not I come. She could have me blow my load, so I will be kept in complete suspense. As I thought about my appointment, I was already becoming undecided in my own mind about my desired outcome. After seeing her pictures and talking with her, I already had a strong desire for the release of a good, strong orgasm under her caressing hands. (After all, it had been 24 days!) I was even thinking to myself that maybe, for this first visit, it would be better to have a nice strong orgasm, then propose the alternate scenario on a later visit, after I knew her better.

I decided to play it by ear, try to get my mind off it until the next day, and go about my business until then.

Anyway, the next day arrived, and I went to her location, a very nice highrise condo. When she opened the door, she was everything her pictures showed and more. She was very pretty, with blond shoulder-length hair and blue eyes. Her web site gave her measurements as 5'4", 110 lbs., 36C-22-34. Those measurements appeared exactly accurate. I told her she looked lovely, and she laughed and said "My clients like that what you see is what you get, which doesn't always happen in this business. You look very nice too, do you work out?"

She was wearing navy slacks, a white blouse, and red pumps. She was about 35 years of age, by my guess, which was really nice for me. I am 36, and I didn't exactly feel totally comfortable trying this fantasy with someone who was, say, 22 – I just figured my odds were a bit better with a more experienced lady.

After checking my ID and confirming who I was, she invited me into the living room, where we discussed expectations. I decided to tell her my fantasy.

When I did, she smiled in a way I knew she "got it", if you know what I mean. "It sounds like you've given this a lot of thought, Pete." I admitted I had, and that it was in fact a lifelong fantasy. She asked a couple of clarifying questions about the ground rules, then asked casually "How long since you've come?"

That's probably when it began to seem real to me – everything out in the open, my load being the focus of her attention, everything being discussed very frankly. I stammered out that it had been 25 days.

She kind of giggled and said, "OK, well, are you ready to take care of the business side?" I placed the money on a table. Then she said, "I'd also like you to show me that you have the other funds you might end up owing." After I did, she showed me into a bedroom and said to go ahead and take my clothes off and get comfortable and she'd be in as soon as she changed.

I'd brought her a little present to wear (a sexy purple babydoll-type nighty – the ladies at Victoria's Secret were able to choose the size based on her measurements) and she had it on when she returned - she also was wearing a strappy pair of purple high heeled shoes.

She had a little alarm clock with her and she set it down next to the bed and turned it away from us. Then she crawled up next to me and rubbed her body against mine, and began to compliment my body, and tell me how much she liked my fantasy, she said it was so nice to be with a really creative guy, she really liked my body, etc (this went on for about 5-10 minutes), and she really was excited to get started. She asked if I was ready to start - she had gotten me really aroused with this "foreplay", and I was extremely ready to get started, if you know what I mean.

So, she slid down my naked body and knelt between my legs (I was lying on my back) - she sort of nudged my legs a little further apart - I could feel the outside of her thighs against my inner thighs and her knees were very close to my scrotum. And then she went to work. Her delicate fingers touched my straining pole, causing it to twitch and jerk immediately - actually we both laughed when that happened. She said, "Well Pete – you're obviously an honest man – that twitch was a 25-day twitch if I've ever seen one." Then she got serious again, cupping my balls in her hand and sort of moving her warm hand around, really slowly. She leaned forward and blew softly on my groin (cock and balls).

The thing I liked the best about her was the way she really enjoyed it and "got it" - she kept talking, real sweet, and saying stuff like "Wow, your cock is huge" (I'm not saying my cock is huge, but she knows that's what any guy likes to hear and she knows it's a turnon, which is what she was trying to do!!), "you must really want to come", "your load would probably fly across the room if I go too far with this."

The tension was amazing, because both of us knew there was money at stake, and she was trying her best to earn it by inducing my request to blow. My mind was still reeling from the fact that I was even in this situation, I was actually in this beautiful woman's bedroom with her hands on my cock and balls. I'd told her my deepest fantasy, I'd even told her the date of my most recent orgasm. She stroked my cock ever so lightly, continuing to pay a lot of attention to my balls.

She described things she'd like to do to make me really come hard. She even took off the pearl necklace she was wearing and dangled it over my groin, letting it touch my scrotum. Then she swung it back and forth, brushing very lightly across my cock, then my balls. She said I'd really blow my wad if she wrapped it around my shaft and stroked me that way, gripping my pole through the pearls.

She pulled the babydoll down off her shoulders, and her 36C tits spilled out. She was looking me straight in the eyes. I sort of gasped a bit. She looked at me and smiled. Then she leaned forward and rubbed her bare breasts on my balls, really pressing into my sack, and manipulating it around, watching my eyes as she did. I began to really squirm, trying to move my pole into the party going on down there. She said, "If only I could put your cock between my tits and bounce them until the come flew, wouldn't that be great, Pete? Do you want me to do that, Pete, because I'm not going to if you don't ask." I needed to come so badly at that point I can hardly even describe it. But I decided to hold out, and hope she went a bit further, since I was so very close, so close to coming that I knew it wouldn't take much of a mistake on her part to make me climax.

She went to a drawer and came back immediately with a pair of black nylons, repositioned herself, and began to very lightly drag the nylon over my balls, then my cock, then back again. Just dragging it, with the only pressure being provided by the weight of the nylons themselves. My cock danced wildly every time the nylon touched it. She did this over and over and over, her tits still exposed. She giggled a couple of times at the way my cock jerked in the air. I had begun to perspire, and nothing seemed very funny to me at that point. When she giggled, her bare tits bounced. She told me that she'd love to stretch and wrap the nylons firmly around my shaft and just start yanking on the ends, just yanking and tugging, while my load splattered all over the room. "You should see it when I do that, Pete, I'd time my yanks on the nylon to the spurts of your load, and you would be amazed at how far the spurts go! Maybe I could do that for you . . . if you ask me to."

Then the whole game changed. She said something that absolutely blew my mind - still does. She said, "You know Pete, if I accidentally go too far with this teasing, and it looks like you're past the point of no return, I'm going to take my hands away before you shoot. Do you know what would happen if my hands pulled away before you shoot?" She kept massaging my balls as she asked this. I couldn't speak; in fact, it felt like I'd almost swallowed my tongue. But, I knew exactly what she was driving at. I hadn't even thought about this aspect of our "ground rules". She answered her own question, and said, "You'd have a very, very unsatisfying orgasm, Pete. I think it's called a 'ruined orgasm', in fact."

I almost swallowed my tongue when she said that - she kept eye contact while it sank in, also continuing to massage my balls in her palm.

Then she said "Pete, I've got your manhood in the palm of my hand. Do you have anything you want to ask me?"

Again, I could not really even speak without choking; I didn't have any response. As it sank in, I began to think about the time - how long had we been together? There was no way to know, and she was beginning to bring me pretty close to the edge.

I waited a couple more minutes, and asked her to make me come - I figured why not - I can't tell you how much I needed to come, and really wanted to come with this beautiful woman jacking me off. She asked me (very breathily) to repeat myself. When I did, she smiled and asked me where my wallet was, went over to my pants, and took out an additional $500.

She left the room with the money, and came back in about 30 seconds, looked at the clock (keeping it away from my view), repositioned herself between my legs and started stroking very softly, up and down my shaft. She asked me how I'd like to come, then she wanted to know how I felt, how far I thought the load would shoot if she jacked me off with her hand. She said we still had some time, would I like to be stroked right up until the end - I said OK.

Then she asked, "Just to clarify, we agreed it would be my decision, right?" I didn't have to ask what she meant by "it" - and I nodded and leaned back and closed my eyes to enjoy the very light stroking - and the suspense. She never stopped talking, making moaning noises, complimenting my cock, etc.

Suddenly, the alarm went off – out time was up. I opened my eyes to look at her - I still didn't know what she would do. She got up from the bed - no hesitation - and said, "Wow Pete, that was incredibly fun!!! You're an incredible man to be able to hold back for that long."

She tossed my clothes to me, put on a bathrobe, and said she'd be out in the living room. It was over.

I dressed, slowly, and walked into the living room. She was waiting for me, and she sort of smiled and asked me if it was everything I'd hoped. I told her it was much, much, much more than I could ever have hoped for. I told her it was like living a dream, and I thanked her over and over and over again. I asked if it would be OK to hug her. She gave me a big smile, threw her arms around me and gave me a full-bodied hug.

She also whispered something in my ear. I can still feel her warm breath in my ear as our bodies pressed against each other.

My cock has really not softened up yet and it's been almost a week. I don't want to masturbate - yet - because I don't want to lose this feeling. Everything had played out even better than my wildest dreams. Then, with one whispered sentence in my ear as we parted, she'd taken it to another level. What she whispered was pretty simple, only thirteen words.

"Give me a call if you ever want to try double or nothing."