Hjh 06

This is the sixth in a series of logs I found on my wife's old laptop about her naughty activities while traveling for business. You may want to read HJH-01 thru 05 first for background purposes.

HJH-06 in her words:

Here I was, a thousand miles from home in San Antonio at a business conference, riding in a cab for a night out on the town with my new 'friend' Jenny. I first met Jenny on my flight to San Antonio. Somehow, in conversation with her, I had shared my newfound fetish of giving hand jobs to strangers on flights I was on.

Meeting Jenny sure turned my world upside down in a hurry. After sharing my 'secret' with her, we somehow managed to simultaneously jerk off the guy sitting between us on the flight. Then, changing seats, I had been on the receiving end of a hand job, not just by the guy we had jerked off, but from Jenny too. Although it wasn't all out sex, I had to consider that my first gay or lesbian experience. And a pretty hot one at that.

Then, on the 3rd day of my conference, I bumped into her in the bathroom. Not only was she attending the same conference, she was staying at the same hotel! What are the odds of that happening?? This first woman to ever have her fingers inside my pussy or touch me in any sexual manner then insisted that she stop by my hotel room this evening so we could have a girls' night out on the town.

When she did show up—earlier than promised, I'm betting it was on purpose—I let her in, still in my robe and on the phone with my husband. Jenny then became the first woman to ever touch her mouth to my pussy, eating me to orgasm while I somehow managed to carry on a phone conversation with my hubby.

And now, here we are, in a cab heading out to do who knows what. Although I was telling myself this is just a couple of new friends going out on the town, I couldn't help but be nervous after what had just happened in the hotel. Our first stop was at a small, quiet bar where we got a semi-secluded booth in the back. Over a few drinks Jenny and I talked about the fun we'd had up to this point. She also pressed me on more details about my debauchery.

"I crave the feeling of a new, strange cock in my hands." I explained. "Feeling it harden in response to my touch. The uniqueness of each cock, the strange man's cum dripping off my fingers." I went on to explain, "Although it was always a fantasy of mine, I had never acted on it until that first accidental one a few months ago. Sleeping and having a naughty dream about a firm penis in my hand, dreaming I was squeezing it. Being in that twilight stage, confused if it's reality or dream and finding my hand on this stranger's thigh, rubbing it. Realizing too late that it was not a dream, I had let him guide my hand over and the rest just happened."

"So that's how my hand job fantasies became reality," I explained, "That first time I had someone other than my husband's cum dripping off my hand was validation to me. Validation that it was time to add more action to my fantasies." It was cheesy but true. "Jenny," I said, "that was the moment I decided that, when I travel, I would transition from Sharon the good wife to Hannah the naughty traveler-Hand Job Hannah."

"Wow," Jenny said, "That's hot. So, before you and I clasped hands around that young man's cock on the flight the other day, how many times had you done this?" "I think Mr. Big Dick that you and I shared was my fourth," I answered, "It's not always easy to find an opportunity on a plane but I sure try."

Then Jenny looked deep into my eyes from across the booth and said, "How about what happened between you and me then?" Blushing deep I looked down, ashamed to answer what I knew was the truth.

The next thing Jenny said to me came in a SHOCKINGLY firm tone. It somehow seemed to be respectful but at the same time I felt it was a demand, almost an order. When I heard her words "Look up at me when I speak to you Hannah," not understanding why, I immediately looked up at her, directly into her eyes, and said "Yes Miss Jenny." Why did I add the Miss in front of that when I addressed her? What's going on here?

Again, she asked, "How many women have you been intimate with then?" I dared not look back down again as I explained to her that it was exciting when she first reached under my coat on the plane and asked me to undo my pants. Fresh off the shared hand job she and I had just given that very well-endowed young man, her hands and fingers felt amazing. "I've never had a...'lesbian' experience in my life before that, nor had I ever fantasized about it," I explained.

With zero shame, I stared her straight in the face and said, "Your hands felt incredible. I've NEVER been touched like that before." "And at the hotel?" she asked. Again, without shame, without looking away, I answered. "I've had my pussy eaten before but NEVER like that. I'd do ANYTHING to feel an orgasm like that again Miss Jenny." I shivered involuntarily, my body recalling how wonderful Miss Jenny's mouth felt.

There I am again, addressing her with 'Miss.' And why did I over enunciate 'anything?' I thought back to my desperate husband at home saying he'd do ANYTHING to experience the feeling of shooting his load down my throat. How that made me feel a shift of control over him, a beginning of some dominance.

'Miss' Jenny smiled back at me again. This time her smile had a sense of satisfaction to it. A satisfaction I didn't quite understand at that point. Looking back at that exact moment I had already subconsciously submitted!

"So," Miss Jenny asked, "You've also explained to me that you have an aversion to the taste and consistency of a man's cum, but you've promised your husband to maybe swallow his load for him in the near future. When we licked the cum off our fingers on our flight, was that the first time you've swallowed?" I couldn't help but notice Miss Jenny was not trying to be quiet with our conversation. I noticed a few heads turning just enough to hint that they might be listening and I think she liked that. "Yes. it was Miss Jenny," I answered without hesitation, trying to mimic her lack of fear of being overheard. "And you've seemingly convinced your husband that you need more practice at it, here in San Antonio? Practice so that you can make it pleasurable for him when you return home?" "Yes, Miss Jenny I need more practice at swallowing cum for the reasons you stated." This time I definitely saw heads turn and Miss Jenny gave an approving smile as if to say she was proud of me.

I patiently studied her face as she then sat quietly for a moment. I could see the wheels spinning. After a bit she said, "I have a proposition for you. Are you interested?" "Yes Miss Jenny." I was beyond curious.

My new friend laid out her proposition, promising she would help me get plenty of practice tasting and swallowing cum so I could perform well for my husband. There would be 1 rule that I must follow no matter what for the remainder of our stay in San Antonio: I must do whatever Miss Jenny says beginning now and lasting until the plane lands back at home, somewhere in the Midwest. We had confirmed that we had the same return flight home.

So, I've had some fun with everything up to this point in my new life as Hannah. I've jerked off some strangers. A woman has fingered me and later eaten my pussy to the most amazing orgasm I've ever had. And I've only fooled around on flights where nothing bad could happen to me. Such as getting mugged, or worse.

Now I'm sitting in a bar, 1000 miles from home, with a woman I don't REALLY know (but DOES have amazing fingers and tongue). It's time to cut my losses, get back to the hotel room, and call my husband to tell him how much I love him. How much I'm looking forward to coming home and sucking his dick until his balls are spent.

So, I look across the table to turn down her proposition. I look straight into Miss Jenny's eyes and say (drum roll please) "Yes Miss Jenny, I accept." WHAT THE FUCK??????? How did my mouth begin forming the word "NO" and "YES" came out instead? My heart began beating in my chest, my nipples hardened, and I could feel my pussy dampen. "Very well then," said Miss Jenny. "So it begins."

With that she began feverishly typing on her phone, all the while smiling that confident smile. After a bit she sat quietly with her arms folded in front of her. I began to ask "What is going..." Miss Jenny put her fingers to her lips in a shushing motion, stopping me mid-sentence. "Patience," she whispered.

I immediately complied and sat quietly. Looking around the bar I noticed some of the people who had overheard our conversations whispering and giving me smiles. It made me think of times I had sat in some bars on previous trips. Far away from my husband, and imagining what then was only a fantasy. Something about tonight told me this was going to be more than just fantasy.

15 minutes of silence passes and then a man approaches our table. "Hello, Jenny," he said. "How have you been? I got here as quick as I could." I don't really remember names from this trip but Miss Jenny introduced us and the gentleman joined us, sitting straight across from me.

Miss Jenny cuts straight to the chase and says, "So Hannah here is working on getting over her aversion to the taste and texture of cum. She wants to get better at it for her husband back home. Do you think you can help us?" I immediately look down in shame but say nothing. "Absolutely," he says. Miss Jenny hands him a piece of paper and says "We'll see you in a while then."

As he walks away, I look at Miss Jenny in shock. As I open my mouth to speak, she puts her fingers to her mouth in that shushing motion again. In my silence she speaks, "Hannah, you looked down in embarrassment again. Please don't do that, OK?" "Yes Miss Jenny," I said.

10 minutes of silence. My eavesdroppers were hanging close by awaiting what might happen next. Another man approaches the table and it's obvious she knows him as well. She repeats the same introduction to him about me being in 'cum tasting' training. This time when she explains how I am needing practice for my husband at home, I shyly look into his eyes, smile, and twirl my finger in my dark curls. I say "shyly" but, somehow, I was becoming more confident in my role and was beginning to enjoy it.

In all, Miss Jenny introduces me to 3 men over an hour's time. Apparently, all people she's maybe been fooling around with when she's here in town. All 3 were handed a piece of paper, probably with one of our room #'s on it. She sends one more brief text and we sit silently for a few minutes.

Her phone beeps and, with no words, Miss Jenny gets up from the table, grabs my hand, and leads me out of the bar. As we passed by our group of eavesdroppers I took the time to put on my brave face knowing what I might be in for. I looked each one in the eye, smile, and lick my lips. They knew damn well (as did I) what I was in for the rest of the night.

After hailing a cab and getting in, Miss Jenny asks the driver to return us to our hotel. As we are riding to the hotel she leans over and whispers an instruction to me. Somehow her order doesn't surprise me and I follow it immediately.

I holler up to the driver, "Hi I'm in town for a work conference. But I'm also here for another reason." To which he replied "Oh yeah, what's that?" "I am in training to learn to tolerate the taste and consistency of cum so that I can please my husband when I get home. What do you think of that?" "I wish I didn't have 2 more hours on my shift," came his reply. "Or I could help you out with that!"

As we approached the hotel, Miss Jenny asked me for a $50 bill (which I had). She folded it over and handed it back to me. "Pay the man," she whispered. At the hotel we got out of the cab and I handed him the $50 and smiled real pretty at him. We almost got to the door of the hotel when he tooted the horn. I looked back and he hollered something out that sounded like "You bet," but I couldn't make it out for sure.

On the elevator Miss Jenny asked me to go back to my room and freshen up. She gave me her room # and asked me to show up there in 30 minutes. She reminded me that I had agreed to do anything and everything she asks for the duration of our time in San Antonio. "Yes Miss Jenny," I said. With that, she got off at her floor and I continued on to my room.

Exactly 30 minutes later I knock on her door and she promptly invites me in. I open the door and step in. There she is sitting on the edge of the bed, legs spread, skirt hiked up, and her bare shaved pussy facing straight at me. "On your knees and start licking," she orders. I hesitate. I had never had sexual contact with a woman until she fingered me on the plane and then ate me out in my hotel room. Being on the receiving end of a 'lesbian' experience was one thing but now being the giver?

"NOW," she repeats loudly. Her assertive tone immediately sets off a tingling in my pussy, my nipples hardening. I stepped forward, in a trance, settled down onto my knees, and placed my hands on her open thighs. "No," she said. "Hands behind your back." I complied. "Now. Lick." I leaned forward and as my tongue found her moist folds, the moan that escaped from her sent chills down my spine.

Miss Jenny gently took my head in her hands and guided the pressure I was applying. I found the taste of her pussy amazing and intoxicating. My first ever taste of a woman's most intimate place.

Enjoying it and also guided by her hands, I settled into a nice rhythm of licking and sucking. Knowing how it feels the few times I've had my pussy eaten well, I tried to ensure my performance was up to par. Slipping my tongue in and out of her wet slit. Teasing her clit and softly sucking on it.

My hands ached to reach for her thighs, to caress their creamy softness. I imagined my hands sliding up her body to feel how hard her nipples were becoming. But I obediently kept my hands behind my back as instructed. The moans from her confirmed I was doing well and drove me to pick up the pace. Soon she was forcefully holding my head tight between her legs as her whole body shook in orgasm.

"Good girl Hannah. This may have been your first time eating a woman's pussy but I'd say you're well on your way to being a pro!" She stood up in front of me and pulled me to my feet. Standing face to face, Miss Jenny pulled me to her, pressing her mouth to mine. As we kissed deeply and passionately, she guided my hands up and down her body. Every inch of her felt amazing. Her face, her neck, her shoulders. Rubbing my hands down her side and her legs, my pussy got so wet as I felt how hard I was making her nipples. The wetness of her pussy as I brushed against it. Soon we were laying on the bed kissing and madly groping at each other with a heated passion I have missed so much with my husband.

Miss Jenny glanced at her watch. "Oh my," she exclaimed, "It's almost 9:30. We need to get ready for the main event." She crossed the room to her luggage and threw me a sexy little black sateen robe. "Strip naked and put this on," she said and put on an identical one, but in a champagne color. A color that made her dominance stand out in a quiet way.

No sooner than having done that, there came a knock on the door. "Come in," called Miss Jenny. I looked up to see the first man that joined us in our booth at the bar earlier, stepping out from the room's entry hallway. She whispered some instructions in my ear. I looked back at her and whispered "Yes Miss Jenny."

I motioned for the man to come closer to me. When he was standing literally inches away, I put on a shy smile, twirled my finger in my curls, and said my new official spiel: "Hi I'm Hannah. My nickname is Hand Job Hannah, and I am practicing to overcome my aversion to the taste and texture of cum so that I can return to my husband and please him. Can you help me with that?"

He undid his pants, pulled his semi-erect cock out and said "Let's see what you've got then." I knelt and looked at the cock hanging in front of me, reached out, wrapped my fingers around it, and there I was again.

Right back where I know my place in life: enjoying the feeling of a stranger's bare cock, growing and swelling, filling up my hand. A little light stroking and he was soon at full mast. As I reached to my mouth to gather some saliva, Miss Jenny instead tossed me a bottle of lube. I held his erection in one hand and squirted a good, liberal amount along the length of his shaft. With both hands I massaged the KY up and down his penis and all over his smooth shaved balls.

He was groaning as he buried his fingers in my dark curls as if to hold me where I couldn't get away. Miss Jenny was groaning from the chair she was sitting in with her legs spread wide and four fingers busy deep in her pussy. I was groaning in total bliss as well. I have no clue how long I serviced him. It was long enough for me to take my time and enjoy it, but I'm sure it wasn't really all that long either. I'm happy to say I HAVE gotten pretty good at this. Soon he was breathing harder and bucking his hips against my strokes. "Don't waste any," shouted Miss Jenny. "Remember what you're training for!"

"HERE I CUM!" he shouted. I aimed my open mouth forward toward his cock just as the first huge spurt shot out, PERFECTLY into my waiting mouth. I felt it hit the back of my throat and leave a trail across my tongue. I immediately began to heave in reaction to it. But at the first sign of my gag reflex he shoved his cock all the way into my mouth, forcing it down my throat. He held my head tight to him, balls deep on his cock. My throat spasmed and tried to gag but I had no choice but to swallow, barely catching breaths through my nose.

He held me like that, tight to his crotch with his hands and fingers twisted up in my hair. He forced me to swallow anything additional that trickled out of him as he softly continued to thrust at my face. We stayed like that until his erection began to soften between my lips. Only then did he release my head. I gasped for breath as his cock slid out of my mouth. "Good girl," he said and firmly patted my cheek with a smirk. "Thank you, Jenny." With that he left the room.

At 10:00 another knock came on the door and in walked the 2nd guy from the bar. I motioned him to me just as I had to the first guy. I put on my shy smile, twirled my finger in my curls, and repeated the pitch. "Hi I'm Hannah. My nickname is Hand Job Hannah, and I'm practicing to overcome my..." and the rest of it. Another erection growing in my hands and out comes the bottle of lube.

I REALLY like giving sloppy hand jobs so having the privacy of being in a hotel room afforded me that opportunity. Hearing my strokes making that slopping noise turns me on and usually turns on the guy I'm servicing. On a plane this isn't really possible to be that loud. But here, at the hotel, is a different story. So, I shot a huge amount of lube onto his cock and balls—he was shaved too—and gave him the sloppiest, loudest hand job he'd probably ever had. Lube was splattering everywhere. My pussy got sopping wet at the sound of my hand slopping up and down his shaft. Slipping over his balls and twisting on his head.

As I worked his sloppy cock and brought him to orgasm, this time I was able to catch his spurts and swallow them all without near as much gagging. I still gagged a little but this time I was more prepared for that first big spurt to hit the back of my throat and immediately swallowed.

I had learned enough with my husband over the years to know that a man cums in quick spurts, almost like clockwork as far as the timing between them. With that knowledge, I was able to time each spurt to swallow quickly and get my mouth back open fast enough before the next rope of sperm arrived. Proud of myself, I was about to pat myself on the back. Miss Jenny beat me to the punch, as she patted me gently on the head like I had earned a gold star, "You're a quick learner. Gooooood girl."