**WARNING** This contains graphic descriptions of _s_e_x_ual intercourse and sadomasochistic activities between two adult males. If this offends you, is not appropriate for viewing in your location, or you are **not** of legal age, don't read it.
**REMARK** This story picks up in the world set up by the stories _Spanking_Party_, _Justin_Returns_, and others. If you haven't read them, I recommend them based on the overwhelmingly positive stream of feedback I've received.
Any resemblance of characters -- other than Jamie -- in this story to the living is purely coincidental. Permission from the real life Jamie, IRC handle: Jamester, was obtained to use our hot discussions as a _basis_ for the story, thank you sweetie! *kiss*
(c) 1997, TopLegal. Permission is granted for distribution via Usenet and the Web in full.
As you already know, I'm a practicing attorney in our great big city. I travel in a circle of hot friends and love to spank among other S&M proclivities.
This story is set several years prior to when Justin moved in with me along with the events described in the other stories in the _Spanking_Party_ series.
Ah, the "information superhighway," gateway to the universe and virtual traffic jams. On it, I've been able to meet hot men from near and far and also get some work done now and then. Mostly the former. :)
I've found IRC to be a fun place to meet hot guys, especially #gayspank and #m/m-spank. Through there and the SwatTeam, I've hooked up with more than a handful of spankees and the occasional spanker when I've felt like going the other way.
One hot boy in particular has frequently connected with me online. A few months ago, I took the liberty of flying him out to visit me for a week.
Prior to ever meeting Jamie, we talked at length and e-mailed for roughly a year. We spoke by phone occasionally also. Sometimes he would spank himself for me via the phone. A hot and very _s_e_x_y type of control. The psychological aspects are very different than for an in person spanking.
The pain/pleasure trade-off is much more in the control of the spankee. And yet the levels at which the spankee are giving themselves over to you are much greater. While it is not the sort of thing I would want to replace my "real" _s_e_x_ life with, it can be hot with the right guy, Jamie seemed like the right guy.
We played phone spanking games involving him choosing an instrument and me a count. That was fun and definitely a mutual turn on.
He opened up to me over time and would regale me with stories of the spankings he found in the middle of our vast country. He shared deep fantasies and desires and I the same.
Also, we talked about wanting to bring someone to tears. It was something he hungered for, and yet was scared of at the same time. I wanted to bring a man there. I had never done it yet. I knew it would have to be done slowly with trust and caring compassion, to bring about just enough pain to elicit tears and yet have the spankee keep wanting more. I knew I could do it with him.
We also talked about using baby oil to enhance the pain of the spanking and sting of the implements. Jamie and I traded information of all sorts on spanking techniques, preferences, desires, pleasures. One of my promises was that when he visited, I would take him paddle shopping and publicly test each paddle on his ass in the stores before selecting the one to use. He would get so turned on by this.
I felt as close to him as anyone I had ever met over the net.
Now we needed it to be real. I wrote the e-mail invitation, most of the guys I meet via the net have not produced the same satisfying contacts that real life meetings have produced. I'm not talking about marriage, I just mean dating/_s_e_x_ual things that persist past more than a one night stand -- or even get that far.
Jamie seemed different and he responded yes to my invitation 10 seconds before I sent it.
I sent off a first class ticket in the US Mail to Jamie. It was round trip and enclosed was a hotel reservation at the Four Seasons. I had never done anything remotely like this before and I didn't want to pressure him. I wanted him to give himself to me willingly, to let me help him live out his fantasy in real life.
I still wasn't sure what to expect. Maybe the chemistry that seemed so hot online and on the phone wouldn't be there when we met. Maybe he just wanted me for my money and the ticket and a top notch hotel was just the excuse he needed to bring him to me but not to give himself to me.
Airports are hideous locations.
Really.
You don't need to spend much time flying to realize that they are not pleasant places to be. Especially since everyone in an airport is waiting for something or someone.
I was no different, I arrived on time and quickly ascertained that Jamie's flight had been delayed. I flirted with some cute guys at the bar while I waited.
Finally I saw the monitor indicate that the flight was on the ground. I headed back over to the gate and waited for the face that went with the picture and voice I had heard so many times.
Soon I saw the cute face and I walked up and gave him a big hug. We chatted and walked towards baggage claim together. The chemistry seemed to be all right.
As we waited at baggage claim, he seemed nervous.
We took his bag out to my beemer and I drove us into the city and took him up to the room. He kissed me.
I took him to the dining room of the hotel. We chatted about life, work, friends, the internet, etc.
Nothing particularly gripped the conversation. I asked if he wanted to come see my apartment. Noncommittal. Would it all fall apart. Would it be another internet-->real life flop?
He begged exhaustion and prevailed on me to pick him up tomorrow, Saturday, morning. I agreed and headed home.
Our society worships couples, and I had missed my dinner with Dave, Rob, Justin -- who I was not dating at the time of this story -- and Tom. Dave and Rob looked like paragons to the world, but I knew better, I knew about the secret mediations with my wooden paddle that held their relationship together. Tom knew of my live-in men, boys, who gave themselves to me. But in reality since Justin had left me, my life had been alone in a certain way.
If you have intimately dated someone you may know what I mean. Justin and I had been so close throughout law school. We lived in a tiny studio together and were as close as any two individuals could be. Then it ended, and although I've had 3 live-ins, four short term dating relationships, and uncounted spanking and other _s_e_x_ partners since he left, it had never been the same.
This probably wouldn't be the same either, but Jamie was so hot, and I wanted someone, a body, so badly.
I went back to the hotel in the morning. Jamie was waiting in the lobby. I took him around the city. Was he ready to buy a paddle? I walked us into the first leather shop in the gay part of the city.
He trembled. I pressed on, we wandered about the store, I told him I would buy him anything he liked in the shop. He selected a hot leather vest, $395, I happily tendered my platinum AmEx card and didn't press the paddle purchase.
We wandered over to brunch at the Palm and Frond, pretentious, gay, in, and expensive. He clearly enjoyed it and liked the vest. As the check came, the waiter flirted with me and Jamie gathered the resolve, that voice I had heard and lusted for over the phone summoned the strength to say it.
"Let's go shopping for that paddle."
My _c_o_c_k_ stiffened under the table. He is hot.
I had four shops in mind and I wanted to go to each of them before selecting one. His howl of pain would decide the purchase, but I wanted him shown off.
We went to the first store, the cashier recognized me from a bar and we chatted briefly before I encouraged Jamie to select a wooden paddle -- with holes -- from the selection of 7 on the wall
He selected a wafer thin looking one that was like a ping pong paddle. I faced him towards me and bent him slightly forward and then lined the paddle up. The other customers turned and watched. **WHACK** The paddle produced a light satisfying thwap, but not quite the **YES SIR** attention I was looking for.
We discussed it for a bit and agreed to try another store. The other customers gawked at Jamie as we left and one definitely followed us, I found it hot.
We hit up the next shop on the strip, and a hot guy was following from a respectful distance. I wasn't known at the next shop and I got Jamie right down to business.
This time, I selected a heavy oak paddle from the wall, it was a decent 1/4" thick. Three rows of holes dotted its foot long, six inch wide landscape. Each hole was a decent 1/4" round.
I pulled Jamie to me and he came very willingly, once again I bent him slightly forwards and put my arm over him. **WHAP** This was quite satisfying. He jumped even with the paddle hitting on his jeans. I was tempted to buy it, but I noticed that hot guy behind me watching Jamie. I wanted to drag this out. There were at least two other stores where I could get a paddle from and I wanted to visit each.
I asked the clerk to put this one aside and said we might be back that afternoon. I stepped out the door and quickly to the side. When the guy following us stepped out I came along side him and introduced myself. He did the same, Frank he said. I more explicitly invited him to join us and we headed to the next store.
This time Jamie selected the paddle, and I bent him over the counter and felt up his ass more publicly. Frank smiled approvingly. **WHAP** This was ok, but the oak paddle from the previous store was my preference. With Jamie still bent over, I asked Frank's opinion as he had seen all three so far. He preferred the second, I concurred, but I took an extra swing anyhow just for kicks. Jamie jumped a bit. I smiled.
We went to a final shop, I wanted to draw this out, but not too much. Frank's presence was nice and clearly made Jamie nicely uncomfortable. The final paddle Frank selected at my request. I administered 3 quick firm strokes, but it just didn't scream out the way I wanted them to.
We headed back to the second store -- skipping the other one I wanted to check out -- and I asked permission to lower his pants in the store. The shopkeeper agreed and right on his bare butt in the middle of the store, with Frank watching, I landed a violent powerful swing on his butt leaving three perfect rows of white holes surrounding the red flesh where the paddle stung. **OUCH!** I found our dream paddle.
I picked Jamie's pants up and kissed him. Then I bought the paddle.
Frank wanted to come over, Jamie didn't want the company, and I agreed with him and sent Frank on his way -- after getting his number -- his part in this excitement done.
We had talked about my apartment, and Jamie had read some diary entries -- not yet public -- which I had shared with him, so he knew what to expect. But holding him here, in my arms was such a rush.
I took my time, holding him, showing him the views of the city, showing him my apartment. Gently caressing him the whole time. My _c_o_c_k_ throbbing in my pants. I wanted him.
I took him to my special bedroom. At that point I didn't yet own the spanking horse, I've described in some of my other diary entries. Nonetheless, the key equipment, seat, bed, paddles, hairbrush, strap, you name it, all abounded.
I had made a point to buy some baby oil earlier in the week, and I hoped it along with the new paddle would be **VERY** handy today. I undressed him slowly, not wanting to rush something I had waited so long to enjoy.
First I took off his belt. I folded it in half and laid it on the ground, even this was a rich symbolic act.
I paused and kissed him, he gave his mouth to me fully and I probed it with my tongue deeply. I reached around and grabbed each butt cheek firmly and squeezed them like the precious items that they represented.
Next I took off his shirt. Then my hands explored his waiting chest.
I caressed Jamie's chest carefully, teasing his firm nipples gently, but not painfully. Then I squeezed his buttocks again, pulling him close to me, and kissing him deeply.
Keeping my hands cupped, I brought both hands down on his waiting buttocks gently -- yet firmly.
Our mouths remained locked passionately together.
I lifted my hands again and swatted his covered ass with my hands cupped. I was testing the waters and we were enjoying each other. I pulled him tightly against me and let him feel my raging boner within my pants and I felt his hardness as well.
I wanted to soak him up, but patience and good sense slowed me.
I slowly undid his pant button and then his zipper. With one hand still cupping his ass cheek, I reached the other down and felt his _c_o_c_k_ through his briefs. Kissing him tightly again, I swatted his ass cheeks firmly twenty or so times with my hand. His _c_o_c_k_ grew harder in his pants.
I then reached in and pulled his stiffening _c_o_c_k_ out of his underwear, and played with it in my hand, I rubbed up it with one hand and spanked his ass with the other. After a few minutes more of this, I wanted him over my lap.
Holding him with one hand around his waist, my palm cupped around his ass cheek, I guided him back with me towards the bed. I sat down and pulled him across my lap carefully. His head and chest were towards my right and resting on the bed. His still covered ass, was squarely over my lap. I carefully positioned his protruding _c_o_c_k_ between my legs and left his legs on the ground.
After squeezing the beautiful hot cheeks through the pants some more, I resumed the hand spanking I had started, this time with more vigor. Jamie began making pleasant ouch's and ah's and gasp's as my strong firm hand worked his covered ass over.
I kept that up for a good hour. Throughout, I would rub his ass, squeeze it, kiss it bent over him and enjoy him. Now, I was ready to up the stakes. I stood him up and pulled his jeans off. After he stepped out of them I pulled him back across my lap as before.
I toyed with his briefs, playing with the bottoms and feeling the warm cheeks underneath the thin layer of cotton that stood between his butt and my hand. I pulled up on the band giving a mild wedgie and also kneaded the butt flesh through the briefs.
Then, I started hand spanking him again. This time he felt it more quickly without the barrier of the jeans protecting him, and within a mere 30 or so spanks, he was making pleasant coo's and ouch's to each swat. I pulled the briefs off without asking and pulled his _c_o_c_k_ down and rested it on my left leg. Now, I could play with it & and spank him. I licked my left hand and moistened it and then began rubbing the exposed bottom of his _c_o_c_k_ shaft while my right hand began to work his hot exposed ass.
This is an ass, I have heard about for a year on-line now. An ass which I have seen bared and spanked in pictures, but one that I had never before had in my control. My hand stroking his _c_o_c_k_ got it rock hard as my other hand blistered butt, there were clear mounds of red soreness at the center of each butt cheek. I moved my right hand around working every inch of butt flesh into a pleasant shade of deep pink.
I licked my left hand again to moisten it and kept rubbing the bottom of his exposed _c_o_c_k_ shaft. I paused the spanking for a bit and kneaded the ever reddening ass flesh with my right hand. Jamie was moaning in pleasure now.
I can't say I blame him. Being spanked **AND** having your _c_o_c_k_ stroked or sucked is one of the most intense pleasure-pain experiences imaginable. I reached over the edge of the bed and picked a jar baby oil I had bought off the floor. First I applied the oil to his _c_o_c_k_ shaft, once that was lubricated and I was stroking it I could feel him ready to cum.
Then I issued the order, "Shoot before I tell you to, and we use that paddle till you cry." Jamie gasped audibly and begged me to stop stroking his _c_o_c_k_. I applied the baby oil lightly to his buttocks and then resumed the spanking with vigor. Each smack of my hand seemed louder and Jamie must have found it more painful because he began struggling which only made me spank harder and stroke more vigorously. I felt certain I could make him shoot so he would have to take the paddle right after orgasm, a much more painful experience than if you haven't shot yet.
After he calmed a bit, I slowed my strokes to his ass AND _c_o_c_k_. I felt he was close. More baby oil on his ass and more firm hard swats of my hand. Every inch of buttock was evenly crimson. No inch of territory had evaded my firm strong hands slap. Now, with more baby oil, the sting would worsen again. My hand smacked his ass harder and harder and I lightened up slightly on stroking the exposed bottom of his _c_o_c_k_ to let him experience the pain that my bare hand could deliver.
Moans and groans of pleasure and pain came from his hot body.
Should I stop? Push him forward? I couldn't decide, I wanted to cum so badly.
I paused, and put some oil on my left index finger and then inserted that into his tight, exposed _f_u_c_k_hole.
INSTANT ORGASM.
I felt his body tense under me and then the release, streaming hot cum shot onto my leg as his balls unleashed a torrent of cum. His body bucked its way up so that his ass was burying my finger. I lifted the cum off my leg and rubbed it over his face forcing him to lick his own cum and experience it.
Once his panting stopped I put him in the window, bare red ass out to the street and city.
I stared at his beautiful youthful face. He is so hot.
But he needed to be paddled.
He looked at me, as if testing my resolve.
I took my pants off and stroked my hard _c_o_c_k_, careful not to cum yet, my cum was for his _f_u_c_k_hole today.
"Stay," I said. And then I positioned the paddle right at his feet and left the room. The paddle was about 12" from his feet so he could see it by looking down, staring at it ominously.
I left the door to the dungeon room open so if he was chicken_s_h_i_t_, he could bail out, his clothing was all there, it was his choice to take the paddle, I went to the living room and turned the TV on, loudly.
I watched the news for a good half hour before returning to the room.
He was standing there still, trapped with uncertainty, he wanted to leave and stay all at once, which would it be.
"Ready," I asked.
"I'm not sure, I want to do this," he responded.
"Really? Why are you still here then?" I countered.
Silence.
"I think you want this more than anything in the universe."
Silence.
"You want me to paddle you so sore, you cry and cry, like a baby in my arms."
"Please, don't spank me," he meekly responded.
"You have wanted this since the first time we MSG'ed on IRC."
"No, please."
"Then leave if you don't want it."
"Please."
"You want this, tell me you want me to spank you."
"No, please."
"Jamie, this is what you have needed all your life, a spanking to let you cry."
"Please, I want to go."
"Then leave."
"I want you."
"Tell me you want me to paddle you till your sore and crying Jamie-boy."
"Please no."
He seems on the brink of crying, but he is still standing, sore ass exposed to the city at my disposal. His protestations seem meek.
"I'll give you some more time to think... when I come back, you can ask for your paddling..."
"Don't leave me, I want it, I want you to paddle me, I trust you, please, I'm scared though, please, paddle my ass sore, please make my cry, please hold me, I want it, I want you to beat me sore, please..."
The words came out like a torrent and I approached and kissed him warmly and deeply on the mouth, reaching my hands around and against the window glass to feel his hot sore exposed ass.
Slowly I walked him over to the bed and laid a pillow in the exact middle. I positioned a second smaller one at the base of that one and helped him lay over it, his _c_o_c_k_ in the dead center of the small pillow, his ass now upraised slightly, his body supported.
From the floor, I lifted the paddle we had bought earlier. I felt its heft, this would scream pain almost instantly, I wanted it to take a while, I would use its power in a measured pace.
I placed my right hand on the small of his back to help him stay put. Then holding the new paddle carefully in my left hand, I hovered it over his ass, gently feeling out where to hit and letting his butt experience the sense of its perfectly smooth wood grain. Pressing down gently to let him feel the holes that would help it swing through the air faster and land more painfully.
Gently, I lifted the paddle into the air, not more than a foot from his soon to be tenderized buttocks and brought it down firmly, yet gently. He reacted calmly, and you could see the outline of the paddle on his ass flesh. Each hole was visible from the surrounding marks. This would be good.
I repeated the gently swats 20 times, accustoming his bare bottom to the ability of the paddle to inflict pain. Gently I worked the intensity of the strokes up to a noticeable level. Now, he felt it and his body began to writhe to escape the paddle's blow. **WHACK** My right hand, kept him mostly in place, but he wiggled his ass mightily. I let go for a moment and applied some baby oil in a thin but total coat over his ass cheeks. The coolness of the oil first produced a sigh of relief, maybe I was stopping.
Then **W** **H** **A** **C** **K** I brought the paddle down at nearly my full force, and the howl Jamie emitted was perfect. He struggled to get up and I kept him down with a single point of pressure on his back. He started begging me to stop. I had no intention of stopping.
I repeated another forceful blow and he started yelling and screaming for me to stop, he was in pain from the paddle. The oil, the force, the holes, everything, it hurt. And he was not able to get hard just yet because I had helped him cum so recently. This was brutal but it was our mutual fantasy coming to life.
One of his hands moved to cover his ass and I quickly pinned it behind his back as I continued to blister his butt violently with the oak paddle. Ten strokes later, Jamie's once white, cum crimson ass was red and on fire, blisters and slight welts were beginning to stand out from the repeated work of the paddle. More baby oil to soothe -- and increase the string.
By the twelfth stroke, Jamie was howling in pain constantly now, even when I paused and kneaded his ass flesh, nothing but painful ouch's, and screams were elicited, he was close to crying. He was close to where we had hoped I could take him, could I do it. I soothed his ass with more oil, and let him rest briefly.
"Stop, please, stop," he began to plead.
"Jamie, we are so close, trust me, I can help you."
"please, no more..."
"Jamie..."
"please..."
I wasn't certain what to do, I liked him and I didn't want to hurt him, but I wasn't certain if he was ready for where I could take him with another 10 to 20 strokes of the paddle to throw the pain past that line where he would finally have to break down crying.
I stood him back in the window and left his now welted and blistered ass exposed. "Think for a bit Jamie, you are so close and you are so beautiful."
I kissed him and left the room, but on my way out, I added, when you are ready, bring the paddle out to me in the living room.
Now, I was waiting for him. Consent is important, trust is important, and Jamie was so perfect and his ass could take so much. By two days from now, none of my handiwork would be visible on his ass and from what I knew of him, he would be able to sit down tomorrow no matter what, he had a tough ass that could really take a spanking.
I sat through a terrible episode of some unknown cable show before I heard footsteps in the hall. I forced myself not to look, if he wanted to leave without finishing I wouldn't stop him.
Soon, there was a beautiful boy with paddle in hand at my side.
"Make me cry."
I took him over my lap and he came eagerly, this is what we had talked about and he wanted.
I worked the paddle like magic, the first new stroke eliciting renewed howls as the hot boy in my lap let me take him to the final spanking frontier.
**WHACK**
**WHACK**
**WHACK**
**WHACK**
Jamie was all screams now and I felt certain that another few would unlock him.
**WHACK**
I felt it coming, his ass would not be able to take too much more.
**WHACK**
**WHACK**
I heard the first sobs as he stopped howling and let himself go.
**WHACK**
**WHACK**
**WHACK**
**WHACK**
A few more strokes produced a wholesale torrent of tears from the boy with the hot blistered ass laying over my lap. I put the paddle down and gently kneaded his sore ass and slapped it periodically keeping the pain level high and letting him cry over my lap for a bit longer. Then when I felt certain that the pain had made him let go and he would keep crying, I slowly and gently sat him up. Then I pulled him against my chest and let him cry.
And cry.
And cry.
We just sat, his body against mine, his head nestled in my chest, him crying.
No words were spoken, none needed to be.
Hours later, when the crying had stopped, I took him to the bathroom and applied ointment to his ass to cool it down and soothe it.
I kissed him, and we went to sleep in my bed, locked in a passionate embrace.
I am grateful to the real life Jamie for letting me share some of our private conversations with the rest of the spanking community. As with my other "Justin" diary stories, the work itself is fictional.
**E-MAIL THE AUTHOR** These stories are basically e-mail'ware at this
point.
My original _Spanking_Party_ was written on a lark and the feedback
convinced
me to keep writing. Continued e-mail means more stores. Keep in touch
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