I heard the door close behind me as I stepped out into the street. It was just after midnight on a Friday. I somehow found my car even though my mind was still back in that apartment. On the drive home, I reflected on the events of the past two weeks, feeling both sadness that I would not see Anna again and, to be honest, somewhat relieved that I would not.
It had been three months since my divorce was finalized, ending four years of marriage. A few weeks ago, I created a profile on a popular dating site with the intent of finding a new romantic partner despite misgivings about entering into another serious relationship so soon.
My encounter with Anna began a week and a half ago and ended an hour and a half ago. It was an exhilarating ten days, well outside my usual experience with women. I cast my mind back to that first day, Wednesday evening of the previous week.
The Beginning
Ping! The sound of a message arriving always created a burst of anticipation. I had not received a single response to any of the messages I had sent out in over three days; had one of them finally responded? I eagerly opened my inbox.
It was not, however, a response to one of my many intro messages; it was an initial message from a profile called ‘Annabel286.’ That was rare, a woman contacting me first! Even more unusual and exciting, it was not a response to my main profile; it was to the other! This site allowed a second profile for those looking for—how shall I put it—alternative encounters of a more intimate nature.
I had tapped into inner fantasies that even my ex-wife was unaware of to compose this profile. It was essentially based on what some refer to as ‘gentle femdom’ with a strong interest in body worship and, more specifically, breast worship and pussy worship. It was to this profile that Annabel286 had responded.
Online with Anna
I responded to her message immediately, and we promptly switched to online chatting. She told me to just call her Anna. I felt this might not be her real name, so when she asked for my name, I improvised hastily. A quick glance at the TV showed an episode of The Simpsons; I replied that my name was Bartholomew, but she could just call me Bart. I felt stupid already, but now I was stuck with it.
We then proceeded to exchange photos. I sent her a simple head-and-shoulders portrait; she said she liked it and did not ask for more. She seemed more anxious to send me her photo, multiple photos in fact.
“I sent you the first photo, Bart,” she messaged. “Tell me what you think—in great detail, please. I love receiving adoring comments, and be sure to include any racy or sexy thoughts that pop into your head; I will be truly disappointed if I fail to produce any.”
The first photo showed her reclined on a sofa, with blonde shoulder-length hair falling naturally on her shoulders, her legs crossed and extended out towards the camera. She wore sheer black stockings, a short skirt, and a tight sweater with horizontal stripes curving around obviously large breasts. She wore no shoes, which allowed the nearly transparent stockings to show off her feet right to the toes. She was making strong eye contact and flashing a provocative smile.
“Beautiful, pretty girl, lovely hair,” I typed quickly.
“Yes, yes, I am most certainly very beautiful, Bart, but you can do better than that, I think. What are you really noticing and thinking? What naughty thoughts have crossed your mind? Is my photo giving you the desire to touch me?”
Well, OK, engaging full honesty mode.
“Big boobs, D-cup, love the sweater; nothing shows off nice tits like stretchy fabric with horizontal stripes, no visible cleavage, but that just adds to the mystery, very likely braless.”
“Wow, Bart, that’s really good. I agree with everything, and it pleases me greatly to hear you say it—or type it, lol. Oh, except for that D-cup comment; they’re double-D, Bart. An experienced eye would’ve caught that, but don’t worry, it will become very apparent in the next photo. Don’t stop there; you’re on a roll. Go for it.”
“OK.” This was getting easier. “I love your legs and the provocative pose with them crossed and extending towards me. I love all forms of black hosiery: pantyhose, stockings, and tights, especially with a sheer fabric like what you’re wearing. I also like that you’re not wearing shoes.”
“Well done again. My legs are indeed fantastic and super arousing in sheer black hosiery. Are they giving you any sexy ideas? I sure hope so, Bart.”
“Yes, I really want to touch them, feel the soft material, run my hand all the way down to the toe, then slowly…very slowly back up and under your skirt until I find out if you’re wearing stockings or pantyhose.”
“Oooh! That’s a great idea! If I were a guy, I would want to do that to me too. Well, what guy wouldn’t really? Maybe you will get lucky enough to try it.
“Well, Bart,” she continued, “I’m sure you would enjoy spending another hour gazing at this photo—heck, even I would—but it’s time to move on to the second one. Before I send it, however, I think it would be more enjoyable for you if you took off all your clothes. I know we can’t see each other, but I am sure you would be more comfortable viewing this one while naked.”
I agreed to do as she requested and soon told her I was ready.
“Great, now that you are naked, I will send the second photo. That is…unless you are feeling a sudden desire to revisit the first photo? I would totally understand that, Bart.”
I knew what she was suggesting—and I almost said yes—but I told her I was anxious to see the second one, which she then sent. It was taken from the waist up, wearing the same striped sweater. She was lifting the sweater up with both hands, flashing her magnificent tits. She was again making intense eye contact and displaying an evil grin that seemed to say, ‘Look all you want, but don’t touch, you lucky bastard!’
I knew by now what she expected of me, so I wasted no time.
“Oh my God, Anna, they are amazing! Huge, natural, and heavy, yet holding a youthful shape. Slightly pointy with beautiful erect nipples. Did I miss anything?”
“They are all that and more, Bart, and I know you must be overcome with a desire to touch them. The important question, however, is, are they causing any changes in your body that you can tell me about? Are you feeling an urge to touch yourself? It would be a totally normal reaction; in fact it would be highly unusual for me not to induce such a feeling.”
I was onboard with her thinking by now, so I wasted no time before playing along.
“Yes, Anna, I could feel movement between my legs from the moment I glanced at the photo. I am fully erect now. I am stroking myself while imagining that I am kissing your tits.”
“Ah, I expected no less. Go slowly, Bart. I know that photo has the power to take you all the way, but there is still one more photo, which you will not want to miss. A photo with the potential to cause a little mess very rapidly and without warning, so be forewarned, and make sure you are ready for that.”
“Please, Anna, send me the third photo now before it’s too late. The first two photos are still open side by side on my screen, a 34-inch screen, Anna. I can’t last much longer.”
“OK, it is sent and it will answer your earlier question about what mysteries lie above the hemline. Do try to give me some wonderful feedback before this photo finishes the job of the first two and ends your pleasure and misery for tonight.”
In the third photo, Anna had uncrossed her legs and spread them wide apart. Her breasts were still exposed, but she was leaning back so you could only see the underside of them and the nipples pointing straight up. It was an up-skirt shot, revealing that she was wearing stay-up stockings with a fancy pattern around the thigh band. She wore skimpy white panties, and I could see curly blonde hair around the edges.
“Oh God, Anna, I want to rest my arms on your legs and kiss your thighs in that fleshy space between the stockings and your panties! I would then lightly kiss you on top of your panties and feel that curly hair on my lips and…”
“Yes, Bart, and then what?”
“Sorry, Anna, the third photo just provoked a messy incident here. I hope you understand.”
“Don’t worry, Bart, I totally understand. In truth, I am surprised you made it past the second photo. It has proved to be too much for some. I tried to limit the potency of the third photo by wearing panties, but I know that image is still very powerful. I mean, it was just too much for you to handle all at once: a beautiful up-skirt view, my curly blonde hair peeking around the edge of my panties, a mile of sheer nylon stockings ending in pretty feet with no shoes, exposed thigh flesh, an underside view of my magnificent boobs rising like twin mountain peaks with lovely nipples at the summits, my trademark intense eye contact, and a highly seductive smile. You didn’t have a chance of surviving that photo; it was unfair, Bart, and totally my fault. Sorry about the mess.”
“Whoa, easy Anna; you’re making me want to run off to the bedroom with that photo. Just warn me next time about what’s to come.”
“OK, Bart. I have to go now. You should come to visit me Friday evening. You will be…in paradise. I will wear that same sexy outfit for you, with obviously the same ultra-sexy body underneath, lol. But Bart, it will be much more intense than these photos, so be forewarned.”
“Yes, I would love to come. Thank you, Anna.”
“OK, I will send you the address Friday morning. The time will be 8pm. I am not available to chat online tomorrow evening, but you have three amazing photos to spend quality time with. I recommend getting naked first, then start very slowly with the first photo. Spend a good amount of time with it before moving on to the other two. This should provide a more relaxed experience. You can tell me all about it Friday; I will want to hear every detail. Goodnight, Bart.”
I went to reply, but she was already gone.
I tried imagining how I would describe Anna’s personality, thinking of terms like vainglorious or self-infatuated, but whatever it was, she was a major turn-on for me. Although I had started out just playing along with how she expected me to react, at some point it became a self-fulfilling prophecy, or perhaps a ‘self-fulfilling fantasy,’ and I was not faking it anymore. At some point, the excitement and adoration on my part became real, and I couldn’t pinpoint when exactly that happened. At any rate, I couldn’t wait for Friday, and I knew that tomorrow, Thursday night, I would follow her advice and start with the first photo; after all, she might quiz me on it.
Meeting Anna
Anna greeted me at the door, dressed exactly as she appeared in her photos. My face must have betrayed my pleasure because she immediately told me—it was not really a question: “You love it, don’t you, Bart? My outfit that is.”
“Yes, you look very beautiful, Anna,” I replied truthfully.
“I know that, duh, but do you find me sexually arousing dressed like this?” she asked with a coy grin. “That’s what matters.”
Before answering, I took a moment to review her attire: a tight, horizontally striped sweater showing off the contours of a matched pair of double-D boobs; a short black skirt; sheer black stockings; no shoes; braless probability: 90%; pantyhose or stockings: as yet undetermined.
“Highly and most definitely,“ I confirmed.
“Good answer! Come in. Make yourself comfortable. You can leave your clothes on that shelf by the door,” she instructed.
I placed my jacket on the indicated shelf and turned towards the kitchen.
“All your clothes, silly,” she exclaimed.
Surprised, I looked at her to judge the seriousness of the request.
“Yup, everything, shirt, pants, underwear, and socks, please,” she added with a smile.
So we’re getting right down to business, it seems. Well OK.
I started to undress, but Anna did not. “Are you not joining me?” I asked.
“Clearly, I don’t need to,” she explained, sounding very pleased with herself. “You just admitted a moment ago that you find me highly sexually arousing dressed just as I am, and I am keen to see, by your ‘reaction,’ if that is true. Wink-wink.”
How could I respond to this? I did indeed say that.
Feeling a bit self-conscious, I nevertheless did as she requested and put all my clothes on the shelf. At least I had already seen her partially nude in the photos she sent me.
“Perfect,” she remarked as she took my hand to lead me to the sofa. “Have a seat while I mix a couple drinks. Is a rum and coke ok?”
“Yes, thank you,” I replied, not really caring what drink was offered—as long as it was strong—thinking it might help alleviate my lingering discomfort with the situation.
She turned to go, but then abruptly swiveled back to me and bent down to closely examine my private parts.
“Is there something wrong, Bart? I am not yet seeing any sign of the reaction that you assured me my attire would produce. Do I need to jiggle my tits or something?”
My penis was at its absolute minimum state, between two and three inches and pointing almost horizontally, not from arousal but supported from below by my larger-than-average balls, which were almost always tight and pushing up slightly. My penis just didn’t have enough length to turn the corner and point down past my large balls, which you’d think I’d stolen from some 9-inch stud.
At a loss for words, I said nothing before she continued.
“Perhaps, like any fire, a small spark is needed to begin the reaction.”
That said, she spontaneously embraced me, pulling our bodies tightly together, and kissed me on the mouth, then just as quickly withdrew and headed to the kitchen to get the drinks. For no more than a second or two, I simultaneously felt three pleasurable sensations: her lips, moist and soft against mine; a black-stockinged leg pressed between my legs, lightly compressing my oversized balls; and her boobs pressed to my chest, one of them shifting slightly and thereby raising my braless estimate to 100%, and then she was gone.
I stood in place, stunned, replaying the sensory memory of the last few seconds—which was still vivid in my mind—while she poured the drinks. Everything must have been ready to pour because she returned carrying the two drinks after less than a minute.
“Ah, now we have the promised reaction,” she purred. “The fire is lit. I am very pleased by the effect I have had on you, Bart; I was beginning to worry.”
I glanced down, certain of what I would see, and I was indeed fully erect. Pointing up almost 60 degrees above the horizontal, now fully four and three-quarter inches—I usually just call it five–and a bit slimmer than average. I like to think the shorter length and smaller girth reduce weight and make it easier to defy gravity and point so sharply upward.
She handed me my drink, motioned me to sit on the sofa, then sat right beside me with her fully clothed body pressed tight against my nakedness. In this sitting position, my still very hard cock was now pointed straight up to the ceiling.
“Cheers,” she said as she raised her glass to mine.
I took a generous drink of the rum, still trying to relieve lingering discomfort in order to be more open to this encounter.
The time had come, I decided, to realize my fantasy from Wednesday night about running my hand up her leg. I placed my left hand on her thigh and slowly moved my hand upwards under her skirt.
Unexpectedly, she placed her hand on mine and stopped me! “No, Bart, not yet. There is something I’d like you to do for me first.”
Unbelievably, she then passed me a fucking computer tablet of some kind and continued.
“Bart, two nights ago online, you described the intense arousal you experienced by viewing my three photos, and you then masturbated while looking at them and thinking about me the last two nights. That really pleased me, and I felt very special knowing that someone would pleasure themselves like that using pictures of me.”
“Go on,” I said tentatively, thinking I knew where this was leading.
“So now,” she continued, “I would really like you to show me how you did that in person while I sit here beside you. The three photos are on that tablet. You can swipe back and forth between them as desired. It would be as pleasurable for me as for you, Bart. Will you do that for me?”
Oh God, this will be tough.
“Sure,” I replied after a moment of stunned silence. I was surprised but had given up questioning her directions. “I will start with the first photo as I did last night.”
“Perfect, the first one is highly arousing, as you well know; I posed for it myself,” she added with a giggle.
I was still hard, so at least I was not starting from scratch. I picked up the tablet, which lit up right away with the first photo, and started to slowly stroke my still erect cock while looking at the tablet.
“Speak your thoughts aloud, Bart, so I can feel that I’m a part of this.”
“OK, feel free to ‘lend a hand’ if you like, pun definitely intended.”
“Oh, that would be cheating, and it would be all over too quickly. Maybe later tonight, if you ask nicely.”
“I really want to see that woman topless,” I started while looking at the tablet and slowly stroking myself. “They must be huge; the contours of the sweater alone excite me.”
I heard Anna sigh with pleasure and lean closer to me. I could feel her right breast press lightly against my left arm.
I abruptly swiped to the second photo, the one of Anna flashing her tits proudly. “Wow, the woman heard my cries, and they are even more incredible than I imagined!” I stroked faster. “I have never seen such beautiful tits, but I think this woman knows that from the expression on her face. I really want to reach out and touch her.”
Anna sighed again, and then I felt her leg press against mine like some kind of cue. I swiped back to the first photo and stared at the long crossed legs in black stockings in the photo.
“Please, woman, extend your beautiful leg and fondle my balls with your stockinged foot. Yes, like that. Don’t stop.”
A quick swipe to the third photo, the most powerful, by Anna’s own description.
“Spread your legs wide for me; give me an up-skirt view of paradise. I love how your beautiful tits point proudly to the sky. I am so close to the edge. Now please, push the fabric of your panties aside and show me your pussy…yes, beautiful, I really want to kiss it.” I came! Straight up and back down on my balls.
Anna exploded with pleasure and excitement.
“That was incredible, Bart. Was it that good last night, or did my presence today add to the experience for you? I’m sure I did. How could I not? I enjoyed that every bit as much as you, Bart. I’m breathless. It made me feel so…desired.”
She left that thought lingering a moment, then turned suddenly, wrapped her arms around me, and kissed me passionately, her breasts pressed to my chest.
“Come with me, Bart. I will clean you up.” She took me by the hand and led me to the bathroom, where she took a facecloth, soaked it in warm water, and gently washed my balls and penis. Even in my freshly depleted state, this felt incredible, and I didn’t want her to stop. After drying me, she had yet another idea. An endless supply of sexy ideas, I thought.
She selected a thin white ribbon from a drawer and proceeded to wrap it around my balls and tie it off above my penis like a cock ring.
“It’s almost not long enough for you, Bart; you could use a cup from one of my old bras to support these things.” Then she added wistfully, “Ah, my lovely bras; I look amazing modeling them. Remind me to send you a picture of me modeling a nice bra. You will not be able to get your clothes off fast enough, believe me.”
Pleased with her work, she turned me to the mirror and said with a warm smile, “Now you are mine, mine, mine; you are so lucky, Bart!“
It’s getting stranger by the minute, but the wording of my profile did open the door to this.
It was back to the sofa in the living room for me while Anna went to pour fresh drinks. When she returned with the drinks, Anna sat in a chair facing me from across the narrow living room instead of beside me.
“We will chat for a while and enjoy our drinks while those large balls of yours produce more fuel.”
“We could even chat about my tits if that would help. It’s a favorite subject of mine. It would absolutely help you regenerate; I guarantee you that.
“Oh, and I am going to steal an idea from your earlier fantasy to test you periodically. I will try it now.”
With an evil grin, she extended her right leg fully across the gap between us and, with her beautiful stockinged foot, tapped the underside of my balls a couple of times.
“Tap, tap, tap. Hello? No response yet. I will try again in fifteen minutes or so. With me sitting in front of you like this, in the same outfit and the same pose as the amazing photo number one, I’m sure it will not take long.” She then slowly leaned back in her chair, crossing and extending her legs a mile out in front of her as in the first photo; the black nylon made a sensuous sound as her legs rubbed together. She flexed one foot up and down, with the sheer, stockinged toe pointing at me. She shifted her boobs slightly as if to emphasize that she was braless. She then looked deeply into my eyes and ran her tongue across her upper lip.
Eventually, I started breathing again, after a sharp exhale.
“I’m even better than my photos, Bart; never forget that.”
Anna’s high opinion of her own sexuality knows no bounds.
Having just come recently, it was easy for me to think that her self-opinion was overinflated at that moment, but I knew that soon, and likely within the next hour, my brain would realign, and I would totally agree with her self-assessment, every bit of it.
“Bart, I am going to re-create the fantasy you experienced earlier, except with me in person instead of with photos of me. I know how arousing those photos are, believe me, but they are no match for…a living, moving Anna! For example, if I slowly raise my sweater like this until I expose what’s called a hint of bottom cleavage, does that affect you?”
I stared at the two bottom halves of her breasts peeking below the sweater. Her nipples and areolas were still concealed. This was my first view under this sweater so far, not counting the photos.
“Yes, Anna, I like that very much,” and even as I said that I could sense movement below. Anna did as well and promptly reached her lovely stockinged foot over for another test.
“Ooo, yes,” she squealed as she bounced my balls up and down from below. “It’s alive and now pointing at my ceiling again.
“You like this, don’t you, Bart?” she stated. It wasn’t a question. “How about this?” She began a series of very gentle upward kicks.
“Yes, Anna, I love it; please don’t stop.” But she did stop.
“Remember the second photo, Bart; we will recreate that pose now. Tell me first what you remember about that photo. Spare no details.”
“You held your sweater up, flashing both your amazing tits. They were large, firm, heavy-looking with a beautiful youthful shape. You had light brown areolas with perky nipples that I wanted to feel between my lips.”
“Yes, you would love that, Bart. Was it like this?” She lifted her sweater, fully exposing both breasts.
“Yes, Anna, just like that,” I sighed.
“Stroke your little cock slowly, Bart, while I show you something that was not in the photo.”
She started to jiggle her boobs from side to side, then held them both in her hands, pushing them together and releasing as I watched them bounce back, lifting them high and dropping them.
“I bet you would love to do this for me, Bart. Am I right?”
“Yes, please, Anna, I don’t think I can take much more of this.”
She then dropped her sweater, concealing her tits from my view.
“Breathe deeply and relax, Bart; we are moving on to the third photo.”
She slowly spread her legs, revealing the same beautiful up-skirt view shown in the photo.
“Go slowly Bart, this is going to get more real and intense than the photo; pace yourself.” She put both her hands on her thighs and slowly moved both of them up onto the flesh between the stockings and her panties.
“Would you like to have your hands here, Bart? Or perhaps your face?”
“Yes, Anna, both.” I could barely speak. “Can I please?”
“Not this week, Bart, but it’s on the program for next week.
“Now I’m going to show you something that was definitely not in photo three. When you get home and review the beloved photo, you will wish it were. Watch closely.”
She took the left edge of her panties in her right hand and pulled the fabric aside, fully revealing her pussy. My heart skipped a beat, and I had to stop the gentle stroking of my cock, or the moment was not going to last long. Her hair was curly and blonde; her inner labia were large and extended outwards towards me, perfectly symmetrical.
“What do you think, Bart? Isn’t my pussy beautiful? You specifically mentioned pussy worship in your profile, Bart. Have you ever done it?”
“Yes, it’s very beautiful, Anna.” I was speechless, staring, wishing I were closer. I badly wanted to kiss it.
“Yes, I know it’s beautiful. Pussy worship, Bart? Have you ever?”
“No,” I said in a barely audible voice. “Never.”
“I didn’t think so.”
“Please, Anna. Can I?”
“Well, OK, Bart, you may sample it. Get on your hands and knees, Bart, and kiss it. I will hold the panty door open for you.”
On all fours, I crawled towards Anna, but with a teasing grin, she raised her right leg and put her stockinged foot on my shoulder, stopping my progress.
“You will need to show me how much you want it, Bart. Either push my leg aside or just give up and enjoy my beautiful legs instead.”
I pushed her leg down under me and continued advancing. My mouth was within several inches of her pussy when I suddenly felt her stockinged foot fondling my hard cock, pushing it playfully left and right.
“Anna, no,” I cried, but it was too late. I felt a pleasurable wave pass through me as I came on the floor below me. I looked back up and saw that the panty door had closed.
“Good try, Bart. Better luck next week,” she said, smiling sweetly at me.
Departure
“Now come with me, Bart, back to the bathroom to wash up.”
She washed me with a warm face cloth again and removed the white ribbon.
“You have advanced to a yellow ribbon now, Bart,” she explained as she tied the new one around my balls and penis and tightened it a little more than last time. “That is all for this week. I will see you next week for the next two steps. Just leave that ribbon on until you get home, Bart, and be sure to put it back on next Friday evening.”
I got dressed by the door, leaving the yellow ribbon in place as instructed. It felt weird to be dressed again, with Anna standing there still dressed like she had been all evening. I had gotten so used to the imbalance created by my nudity that it now felt wrong to be attired as an equal.
“See you next week, Bart, Friday, 8 p.m,” she confirmed.
I hesitated a moment before answering. I was experiencing feelings of mild frustration about the slow progress of this relationship. Granted, it was erotic, fun, and certainly a new experience. She immediately sensed my hesitation and interrupted with a request.
“Give me your hand, Bart.”
I extended my right hand, which she took in her right hand, and with one smooth motion, put my hand under her sweater and placed it cupping her left breast, then just looked intently into my eyes and said nothing.
I absolutely fucking melted! I felt a wave of pleasure that made speech difficult and my legs unsteady.
“Ah, er, yes,” I replied in a weak, trembling voice. “I’ll be here next Friday, 8pm.”
“I’m glad, Bart; don’t worry, all will be wonderful next week; you won’t be disappointed,” she promised, then added, “I will send you some more photos to help keep your fire burning and for added practice—wink-wink.”
With that, she removed my hand and wished me good night, then disappeared inside.
Walking back to my car I was confused about why I had reacted so strongly—or weakly, I should say. I had been fondling boobs of all shapes and sizes for over 20 years, for Christ’s sake. My ex-wife had great tits, so why did this one breast have such power over me? I could only guess that, through skillful use of some form of tease and denial, she had built up a level of anticipation over the last few days that suddenly resolved when least expected. At least that was my theory.
When I arrived home, I checked immediately for messages containing new photos—nothing. I checked again about four times that night and every hour or so the next day. I knew with certainty that I would be back there next Friday, no matter what form of crazy erotic fun she had in mind. I was hooked, and I knew it at that moment when I was standing by the door with a DD-cup tit in my hand.
It occurred to me that I had never read Anna’s profile on the dating site; she had initiated contact with me, and we had gone directly to chatting. Out of curiosity, I looked it up and found that it was very brief; there were no pictures and just a single line of text:
“Profile of Annabel286, Déesse. I…will contact you.”
I googled the unfamiliar word and was not at all surprised by the translation from French that it produced.
The following week, I learned what really motivated and satisfied Anna sexually, and it explained so much.
