A Lost Bet Ch. 03

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"Roll over," he said. Slowly, I rolled over onto my back, feeling relaxed and sensual. It was a very different experience than the other times that I had been used by Frank. "Keep your eyes closed," he said. I felt him start to rub the front side of my legs with lotion and I couldn't believe that the massage was continuing. I started to peek at the clock when I heard him say "you're stubborn to the end aren't you?" But there was no malice or harshness in his tone. Not even the commanding nature that had characterized our other encounters. "I guess there are some things that we just won't be able to change," he said as he reached up and softly closed my eyes for me. "Since you seem to want to peek, against my requests, I'm going to blindfold you. After I do that, please, just try to relax...for me." I didn't say anything, but I did raise my head so he could slide the blindfold over my eyes.

"Now, back to the massage." And he started up right where he'd left off...rubbing the front part of my legs and working his way up to my thighs. As he got closer and closer to my groin, I felt myself start to harden, even while tucked away in the teddy.

The next touch surprised me. Frank started to spread my legs and he pulled my penis loose. His lotioned hand started to stroke it slowly, gliding up and down, until he decided to tuck it in the front part of my teddy, trapping it against my stomach. I was in shock because in our past two encounters, Frank had never really acknowledged that I even had a penis, let alone touch it. Tom had been the one to put it in captivity the other night. So for Frank to touch it at all left me shaken and quivering with a desire for release that had long been denied to me.

Frank continued to massage my front...my thighs...my hips...my stomach...then he reached my chest. I wished I could see what he was doing but the blindfold made it impossible. I could only wait for the next touch, imagining where it would be. Then, it came. The soft touch on my nipples and my pecs/breasts. Frank started to massage them slowly, rubbing them all over then teasing the nipples through the teddy. He pinched them, but not to cause pain. But with each pinch, I still gasped and I felt my body arch as he pulled on them lightly. I'd never known a feeling like this. I almost wished he would continue...until I felt his hot breath on my right nipple as he started to lick it through the teddy. He licked it, then sucked it and I moaned. I felt myself starting to squirm with a pleasure that had been denied to me before. I thought to myself "my God...if this is what girls feel when guys are kissing on them, it's no wonder they like it..." I had no time to pause and consider the changes in my thought process because Frank moved to my left nipple and started the process all over again. I lay there, soaking in the experience, feeling myself moving closer to a precipice I never thought I'd reach with a man...a point that I'd never considered reaching with a man because I wasn't gay (was I?). I knew that I was moving towards a climax, but wasn't there yet. I was somewhat ashamed to be this aroused under the ministrations of another man, but I didn't want it to stop.

Frank pulled himself away and I heard myself utter a moan of a disappointment. I couldn't believe that the sound came from me, but a part of me didn't care. I found that I was enjoying the experience of being on the other side of things. I wasn't the aggressor. I wasn't expected to be in control. I knew that I was still a participant, but for the first time, I started to really feel out of control...in a good way.

"If you're enjoying yourself more than you thought you would, nod." I nodded. Slowly, but with no hesitation. "Good," he said. "Finally, you're coming around to the possibilities of what could be...at least in this time and place."

I felt his weight come back on the bed, but I could feel him at the foot of the bed. As he moved up the bed, he spread my legs wide and situated himself on top of me. He didn't rest his weight on me though. I could tell he was using his arms to support himself as I felt his breath on my neck. Then, a nibble on the right...a nibble on the left...a little tongue in my left ear...a gentle kiss on my forehead...a light tonguing of my right ear. My breath was coming in sporadically and raggedly. I could feel his dick pressed against my balls while my dick strained against the teddy. I could feel his stomach pressed against mine. I reached out and felt his arms taut, supporting his body. Then...I felt his kiss on my lips. Lightly he kissed them. His tongue caressed my lips and parted them. I responded to his kiss as though I had no control over my own body. Deeper and deeper he kissed me and I felt myself rising to meet him. I wished I could see, but I settled for feeling as I wrapped my arms around his back.

We continued kissing and rubbing our bodies against each other for a few more minutes before I felt Frank pull away again.

"Roll over, but stay lying down on your stomach."

I rolled, then waited for the next sensation. Again, I felt Frank spread my legs and position himself between them. I felt his hands on my ass, spreading my cheeks apart so he could find my hole. As he started to tease my hole with his fingers, I felt the coolness of the lotion dripping in. I tried to relax as he slid his fingers in...first one...then two...then three...I squirmed and he used his other hand to put pressure on my lower back, keeping me in place. I started to breathe ragged little breaths as he finger-fucked me for a few minutes, but I was mildly surprised as his slid his fourth finger into my ass. I gasped and tried not to move while I got accustomed to this sensation. This was so different from the invasion I had experienced from the vibrator on the machine, or the beads, or even from the cocks of Frank and Tom. This was a little more tender...a little less pressured...and a little more unpredictable. That last thought hit as he started moving his fingers around in my ass, causing me to sharply inhale right before a little moan escaped my lips.

"Are you ready?" he asked.

"Ready for what?" I replied. Only I didn't get all of my answer out because right in the middle, Frank started forcing his entire hand into my ass. "Wait...wait...wait..." was all I could manage to get out. Even though he was going slow, the pressure was amazing and I had never been stretched quite like that. "Oh God...it's too much..." I moaned into the pillows. But Frank didn't stop. He pushed, added lotion, then pushed some more until his entire hand was up my ass. I didn't move. I just lay there reveling in the mix of pleasure and pain praying that he wouldn't move...because then I'd have to readjust.

"I'm pulling out now." And he did just that. Slowly, gently, he removed his hand from my ass and I was left shuddering on the bed trying to get my mind around the fact that I had just had another man's hand ENTIRELY up my ass. I wasn't able to ponder the thought long though, because Frank moved on top of me and gently eased himself into me.

This was different. I wasn't bound. I wasn't being handled by two guys at once. It was one man on top of me, slowly, almost lovingly, fucking my ass. For the first time, I didn't feel like I was being assaulted...I felt...sensual. Feeling his weight on my back with his dick in my ass, I wanted to move against him. Even as he fucked me, his hands caressed my arms and pulled them above my head where he intertwined his fingers with mine. His fucking was slow and luxurious and it forced me to grind my own dick into the bed. With each of his thrusts, my cock was caressed by the mattress and teddy giving me my own special pleasure. Thrust after thrust from Frank and my pleasure built.

"Oooh Frank," I moaned. "I think I'm gonna cum."

"That's good Jo...that's good...I'm not far behind you."

Frank started pumping faster and his pressure on my prostate combined with the sensations from rubbing against the teddy made me feel like I was going to burst.

"Please...Frank...please...quick...can't hold on..." My statements were jagged. My breath was ragged. My body was starting to shake from the exertion and the pleasure. I felt muscle twitches all over my body and second after prolonged second, I tried to hold on until I could go no further. "Mmm...ooo...uunnhh...mmmm...!!" was all I could sputter as I came all over my stomach. Then Frank started grunting...harder and harder...and his pounding reached a new level until finally...he came with a bed-shaking, toe-curling orgasm. My mouth was open in a silent "O" as I tried to breathe under the pressure. My hips bucked as Frank spurted jet after jet of cum into my ass. After he was done, we lay there for minute after minute, trying to breathe and recover our spent energies.

Finally he spoke. "So...was it good for you?"

I laughed. I didn't mean to. I never thought I would. But I did. I giggled and said "yes."

"See what can happen when you just relax?" I could hear the smile on his face as he spoke. Slowly, he let go of my hand and began to trace the outline of my body with his finger. I shivered at his touch, but I longed for more.

"Jo, that was the way things should have been. Maybe if we'd started there, you wouldn't have been so resistant all along."

"No. I disagree." I stated. "I never wanted any of this to happen. At least not on a conscious level. Now that it did, I'm still not entirely sure how I feel about it."

"Oh really?" teased Frank as he ran his hand over my nipples and then down to my softening cock which twitched involuntarily in his hand.

"Yes Frank. Really. I'm not going to lie to you though, and say that I didn't enjoy what just happened. I mean, that was amazing...and surprising...and sensual...and scary...and enjoyable. And I guess that while we're here on this trip, I'll go along with some of your games and plans. But once we get back, I want my life back. I want my manhood back."

"Okay Jo. I can respect that," said Frank as he continued to caress my body. "Let's deal with the real world once we're back in it though. Is that a deal? Can we just enjoy the moment and let tonight be tonight and this trip be what it is?"

"I suppose so," I mumbled through a yawn. "Damn, I'm tired."

"I know. I've got skills," Frank laughed.

"Oh, don't try to get a big head about things. You forget, I was already tired from skiing."

"Potato, po-tah-to." Frank continued to laugh lightly as he nuzzled my neck. "Go to sleep, but don't be surprised if you get woken up later on."

"I won't. I know you well enough to know that I need to expect the unexpected." Then I turned my head, pushed myself back into Frank's embrace and passed out dreaming of what the next day would bring.

To be continued...

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SissyBoy1WarszawaSissyBoy1Warszawa8 months ago

I will say that this part fell to my heart more, it was very romantically erotic and very nice Frank without coercion and even gently and in a nice atmosphere after massage, caresses led to Jo accepting his hard cock in her hole (male pussy). This is how I would like to be treated myself, caressed, massaged like Jo by Frank. I like this story more and more, I became very close to Jo. I'm already thinking about how things will turn out for Jo and will she become a real Sissy submissive for Frank, Tom? Or will he choose just one of them or someone else entirely? 🧒🏻👧🏻💋🍦💦👅🧑🏻‍♂️👱🏻‍♂️.

ps. Sorry for grammatical errors and inaccuracies, but I don't speak English.

SissyBoy from Warsaw, Poland. 👩🏻❤️👩🏻‍🦳.

Powiem że ta część bardziej Mi przypadła do serca, była bardzo romantycznie erotyczna i bardzo ładnie Frank bez przymusu a wręcz delikatnie i w miłej atmosferze po przez masaż, pieszczoty doprowadził że Jo przyjął jego twardego kutasa w swojej dziurce (cipce męskiej). Tak bym chciał/a sama być potraktowana, pieszczona, masowana jak Jo przez Franka. Co raz bardziej podoba Mi się ta historia, bardzo zżyłem/am się z osobą Jo. Już myślę o tym jak potoczą się losy Jo i czy zostanie prawdziwą uległą Sissy dla Franka, Toma? A może wybierze tylko jednego z nich albo kompletnie kogo innego? 🧒🏻👧🏻💋🍦💦👅🧑🏻‍♂️👱🏻‍♂️.

ps. Przepraszam za błędy i niedokładności językowe ale nie znam języka angielskiego.

SissyBoy z Warszawy, Polska. 👩🏻❤️👩🏻‍🦳.

AnonymousAnonymousover 17 years ago
Trans &

They really should make this a sub category of Gay. Everything I have seen her in the TV/TG category is either Femdom or Gay.

Be honest about your plot line and characters sexual actions, you will get a higher score from me.

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