A Ride to Change Ch. 02

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No longer tripping, Jimmy has no regrets.
3.5k words
4.81
7k
7

Part 2 of the 2 part series

Updated 06/10/2023
Created 07/28/2021
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BenJacnov
BenJacnov
226 Followers

I was the first to wake up. As I became conscious of my surroundings last night came rushing back to me. I had been picked up hitchhiking by these two and we had sex. My thoughts were interrupted by an urgent need to pee. Lonnie and Toni were laying on their sides; their backs to me. I carefully slid down to get out of the bed without waking them.

As I stood over the toilet emptying my bladder I thought about the night before. "Holy fuck! I had gay sex last night." Being sober I knew I couldn't blame the Mescaline for what had happened, but I thought that without it distorting my perception and lowering my inhibitions I would have never been in that situation. I realized there was no need for excuses. "The truth is," I told myself, "you enjoyed last night very much."

When I returned to the bedroom Lonnie had rolled onto her back. It was easy thinking of Lonnie as she wished to be. She was beautifully feminine. She just happened to have a big cock. I couldn't believe the rush I got looking at it laying on her belly in its semi hard state. I remembered how it felt in my mouth just a few hours ago and I found myself wanting to experience those sensations again.

I eased back up onto the bed and took her beautiful cock in my hand. Kneeling beside her I raised it and slid my mouth down over the head. The sensations coursing through me as my tongue brushed across the velvety smooth flesh convinced me that last night was not just a drug induced reaction.

I gently sucked and rimmed the head of her cock until it grew completely erect. I heard a soft moan escape Lonnie. I used my tongue to bathe her cock from the tip to the base. I gently sucked on her ball sack enjoying the squishy feeling of a nut as I rolled it in my mouth. Releasing her nut I let my tongue glide back up the shaft to the tip. I lowered my mouth down her shaft taking it as deep as I could without gagging.

I continued to suck her like that for a few minutes; getting bolder with every stroke. Before long Lonnie's hips were humping my mouth with small movements. I increased my efforts to bring her to orgasm; anticipating her cumming for me.

My movements woke Toni. "Oh Sugar, you really do like sucking cock don't you?" His observation was true. He got up and went to the bathroom. When he came back I felt him get on the bed behind me. He took my dick in his hand and pulled it back between my legs so he could suck on the head. Toni was holding my balls and dick as he used a lot of suction. It felt really good stretched tight like that while he sucked me. The more I got aroused by Toni, the more I increased my efforts on Lonnie.

Toni stopped sucking my dick and ran his tongue across my asshole. It sent shivers through me in waves of pleasure. I've had fingers brush across my anus many times, but Toni's was the first tongue. He started alternating between sucking my dick and tonguing my asshole. When his tongue entered me I felt my dick throb in his hand. I moaned with the wonderful sensations he was giving me.

Lonnie's moaning became more pronounced as she humped her dick into my mouth with determination. Then I felt her hand on the back of my head just before she moaned loudly and came, flooding my mouth with her hot, silky cum. The feeling was still as erotic in that moment as it had been the night before. I greedily sucked all the cum from her cock as she ejaculated. I swallowed every drop of her creamy fluid before releasing her from my mouth.

"Good morning, Jimmy. How was breakfast?" Lonnie cooed.

"Wonderful, and good morning to you too."

Toni was still behind me. He was no longer alternating, but stroking my cock with his hand as he ate my ass. His tongue was arousing me to a level I had never attained before. I was close to cumming when Toni stopped what he was doing and said, "Sugar, I still want to fuck your sweet ass."

Hearing that brought me up short. As good as what he was doing was making me feel I still wasn't sure about taking one in the ass. "I don't know, Toni. That might be going a little too far. I am kind of afraid. I just don't think I want to do that."

Toni started stroking my dick again as he spoke softly. "Well, you will never know if you will like it or not until you try it. Remember last night?"

Toni was right. I had discovered that I liked sucking cock last night, but I never would have believed it before trying it. "Oh god. Okay, but please stop if I tell you to."

Toni, his voice trembling with anxious anticipation, said, "I'll go slow and be gentle. If you want to stop at any point I will. I promise. Come with me so we can get you ready." He bounded from the bed heading to the bathroom.

I realized then that I was committed so I followed him to the bathroom. Toni grinned and patted me on the ass when I walked in. "Here, take this and sit on the toilet before putting the nozzle up your ass.

What he had handed me was a small hose about five feet long with a nozzle that was about six inches long and perforated. The hose was attached to an old fashioned water bottle that was hung on the wall beside the toilet. "Okay Sugar. This is how we are going to clean you out so the sex won't be messy. I have already filled the bottle with warm water for you. All you have to do is sit and insert the nozzle, then open this valve. The water will flush your rectum and lower bowel. It's gonna be a little messy, but be careful and it won't be bad. After you finish, clean yourself up and come back to bed."

Toni left then. I had never done something like that before, but I figured it out. When I returned to the bedroom Toni and Lonnie were lounging on the bed watching me walk across the room. They were stroking each other's cock nonchalantly. As I got on the bed beside Toni he reached out and wrapped his fingers around my dick. Then he kissed me.

I enjoyed both their kisses as much as any kiss I ever had. It was definitely a, I want to devour you, kiss. When we broke the kiss I was breathless. Toni asked if I was ready. "I, I think so. C-can I suck Lonnie's cock while you do it?"

I was very nervous and a little afraid taking my cherry was going to hurt. I thought if I could distract myself with Lonnie I might not be as tense when Toni tried to penetrate my anus.

Toni shook his head. "No, Jimmy. At least not the first time. I want you to be fully aware of every moment of this. I am happy and honored to be the first to give you this experience. Okay, lay down on your back and spread your legs for me. I think it feels much better in that position to start. Here, I have some lube that will make things much more comfortable for you."

I rolled over onto my back and Toni got between my legs. He opened the small tube and squeezed out a small dollop of the gel. I felt his finger stroking my anus. The gel he applied made my ass crack very slick. He slipped a finger into my asshole and I tensed up. "Relax Jimmy. I promise I won't hurt you."

As Toni continued to slide his finger in and out of me a warmth started to spread through my rectum. The gel must have had a warming agent in it that was activated by friction. The feeling was pleasant and his finger in my ass actually started feeling pretty good. Lonnie kissed me while running a hand across my nipples. Then she got up and went to the bathroom. I wish she would have stayed to distract me from what Toni was about to do.

Toni inserted a second finger in me and this time I welcomed the invasion. His fingers were causing the sensations in my asshole to radiate through my whole bottom. He moved up and tongued my nipples. I moaned and arched my back putting more pressure against his tongue. I never knew how sensitive my nipples were and I regretted that fact. He kissed his way to my dick, never stopping his fingers pistoning in and out of my asshole.

Lonnie returned from the bathroom. She grabbed two pillows and told me to raise my ass. She put them under me raising my hips off the bed. She sat on the edge of the bed, took my hand and was just holding it, smiling at me. "Toni will be super gentle with you, Jimmy. Don't worry.", she whispered.

Toni continued to suck my dick as he fingered my asshole. Between the two I was so aroused I failed to realize he had added a third finger until he sat up and said, "That's three fingers, Jimmy. I think you are ready."

In spite of my arousal I tensed up again at the thought of what was coming next.

Lonnie leaned over and put her lips on mine. She kissed me lightly. "Relax, Jimmy. Just breathe and unclench your ass cheeks. Toni will go slow and it won't hurt. I promise."

Listening to Lonnie, I realized that I trusted her and relaxed the muscles in my backside. "Okay, go slow please." I pleaded.

Toni gently pushed the head of his cock against my anus. We were looking into each others eyes. He smiled as his cock pushed into me, expanding my sphincter as it did. As loose as he had gotten my sphincter, it still felt tight with his cock in me. He stopped with his cock head in my ass. "You okay, Jimmy?"

I finally took a breath and said, "Yes, I'm alright. It doesn't hurt, but feels weird and good all at the same time. Go ahead, Toni, but just take it easy, OK?" My legs were in the air, the backs of my knees resting on Toni's upper arms as he supported himself on his hands. He started pushing. It felt uncomfortable as his cock filled my rectum. I could feel it as the shaft slid past my stretched sphincter.

When he got about half of his cock in me he slowly pulled back out until just the head remained in me. He reversed course and pushed back in, but didn't go any deeper. He started slowly fucking me like that for several strokes. I was totally relaxed now and his cock was feeling really good. I was moaning on every inward stroke. The uncomfortable full feeling was replaced by indescribable sensations as his cock filled my ass.

"OK Jimmy, here we go. I'm going to give you all of it now.", Toni warned.

Before I could respond he slowly pushed until his hips were against my groin and his dick was completely inside my ass. He was balls deep in my ass and I couldn't believe how incredible it felt.

Toni quizzed me. "You still okay, Jimmy? What do you want me to do; stop or keep going?"

I sighed heavily, "No, don't stop. I'm okay. Oh my god. This feels incredible. I want you to continue. Take it easy and let me get use to it though."

Toni started withdrawing and my whole body shook as I felt his dick slip through my sphincter. It even felt better as he pushed all the way back in. He fucked me slow and easy as I got use to him in my ass.

Then on a stroke out Toni pulled back until he came out of my ass completely. The head of his dick was resting in my ass crack, the tip kissing my puckered asshole for a moment before he pushed back into me. The feeling as his dick slipped back in past my sphincter with no resistance was fantastic.

The sensations coursing through my ass as my sphincter stretched threatened to overwhelm me. Desiring more of that treatment I exclaimed, "Oh fuck, OH FUCK! Do that again!" Toni did. He started withdrawing completely, then pushing a couple of inches in me repeatedly. I was amazed by the lack of resistance. The feeling of his dick stretching my asshole open on every stroke was driving me closer to the edge. Lonnie was still holding my hand, although I no longer needed reassurance.

Without warning Toni drove his cock deep into my ass. The sensations that flooded over me when I felt his full length in my ass caused me to moan loudly with pleasure. Toni pulled out and said, "Roll over and get on your knees. I'm going to give you a proper fucking."

I quickly flipped over, moved the pillows and pulled my knees under me, then raised my ass in the air; anticipating welcoming the penetration. Toni mounted me and drove his dick in my ass in one swift motion. His hips slammed against my ass cheeks; his balls slapped into mine. I grunted from the force of his insertion, but it didn't hurt. He started pounding me hard. Every stroke in, I grunted. "Uuh"

His dick slamming my asshole was driving me wild with lust. I was pushing my ass back to him, meeting his every thrust. Begging for more, I could feel my orgasm fast approaching. That astonished me because my dick hadn't been touched since Toni started fucking me.

Suddenly Toni stiffened with his dick buried deep in me. He started moaning as he filled my ass with his hot cum. His dick throbbed with each ejaculation. I had just been thoroughly fucked for the first time in my life and I loved how good it felt. Toni asked, as he slowly pumped his deflating cock in and out of my very wet and loose asshole, "Well, how did you like that, Jimmy?"

Without reservation I told him, "That was the most intense thing ever. I liked it very much. I am so glad you convinced me to try. Now I am in need of getting off badly. Could one of you help me out?"

My dick was rock hard and throbbing. All it would have taken at that moment was for one of them to touch it and I was sure I would have spewed cum everywhere. Hoping one of them would suck me to orgasm, I started to move forward so I could slip off Toni's dick, but he grabbed my hips and held me in place.

I panicked a little when I heard Toni say, "Do you want some of this Lonnie? I have him lubed enough that I think you can get in here now."

I forgot about my emanate orgasm as Lonnie moved down the bed to kneel beside him. Sure, Toni's dick felt wonderful in my ass, but Lonnie was so huge. I was afraid she would never fit and rip me apart. I should have known better after watching her fuck Toni last night, but I was too nervous.

Toni pulled out of my ass and playfully slapped me on my right ass cheek. He said, "Tear it up, Lonnie. Show Jimmy what a real dick feels like."

Lonnie moved in behind me. I could feel Toni's cum running down my inner thighs as it drained from my asshole. I pleaded, "Oh my god, Lonnie. I can't take that! Please don't."

She put her hand on my shoulder and pulled me upright against her chest. I could feel her hard nipples pressing into my back. I turned my head to look at her and she kissed me lightly on the lips. Her hand snaked around me to grip my hard dick and softly said, "I will go real slow, Jimmy. I won't hurt you, I promise. We haven't hurt you yet have we? Now bend back down so we can do this."

With trepidation I assumed the position. When I didn't feel her cock head against my anus I looked back to see her smearing more lubricating gel on her massive cock. I was thankful for that. She rubbed her dick head across my anus and as hesitant as I was, the tingles that sent through me was a surprise. She held the tip against my anus and pushed. I just thought Toni had stretched me. I felt my asshole expanding more and more as she slowly entered me.

I was super glad Toni had gotten me as loose as he had. The pressure of Lonnie's cock as it pushed into me was almost painful. Then suddenly she was inside. There was a flash of sharp pain, but it was so brief I barely noticed. Only the head of her cock was in me, but she was in. She sawed back and forth through my sphincter with the head of her cock until it loosened it's grip. It was starting to feel incredible as her thick cock stretched my asshole to accommodate her size. Toni's cum proved to be a good lubricant.

Every time I got comfortable she would add another couple inches causing me to moan loudly. Finally I felt her hips bump against my ass cheeks. She was completely inside me. I could feel the pressure on my prostate. The feeling was a little uncomfortable, but not unpleasant.

Lonnie reached around and grasped my dick. She slowly stroked it. "There. You have it all, Jimmy. How you feeling?"

"Oh my god, I can't believe you got the whole thing inside me. I feel so full. Please go slow and take it easy, but I want you to keep going."

Lonnie let go of my dick and put her hands on my hips. She started fucking me real slow with long strokes. The more she stroked the better her cock in my ass felt. The feeling of her cock sliding through my sphincter with each stroke in and out of my ass was amazing.

Toni lay on the bed so he could wiggle under me and suck my dick. I can not even describe how awesome it felt having his mouth on my cock and Lonnie's cock in my ass. My orgasm was immediate. I shook all over as I came in Toni's mouth.

Lonnie had picked up her pace and now she was fairly pounding my ass on every stroke. Not real hard, but forcefully. The sensations from her pounding coupled with my orgasm washing over me was almost unbearably pleasant. "Yes, yes. God, you feel good. Fuck me Lonnie, just like that. Yes, give it to me, baby."

With wild abandon I succumbed to the moment. Lonnie gripped my hips tightly as she hammered into me. I was coming down from my orgasm as she slammed her hips against my ass and held still. I felt her cock throbbing and the heat of her cum as she emptied her balls in my bowels. We were both moaning in pleasure. When Lonnie finished cumming she stroked me several times before slowly withdrawing her cock from my ass.

It felt incredible as her semi hard cock slid out of me and my sphincter slowly collapsed. I missed the feeling of her in me immediately. As she collapsed onto the bed beside me she said, "God damn, that was good, Jimmy. Thank you for letting us share this experience with you. I know you were scared, but damn man; you have a fine ass. I enjoyed that a lot."

Toni was laying on my other side. He spoke up. "Yeah, I enjoyed it too, Sugar. For someone who was unsure if they wanted to try it; you sure did enjoy it, didn't you."

He was right. I did enjoy it. More than any sexual experience I had ever had. I knew I loved sex with women and could not conceive of giving them up for this exclusively, but I knew that looking forward, I would repeat this experience again and again. Any woman who formed a relationship with me in the future would have to be willing to share me with another man or at least let me indulge my desires on my own.

"Yes. I have to admit I did enjoy it with both of you very much. I really am glad you stopped for me last night. You two have opened me up, no pun intended, to so many feelings I didn't know I had. The experiences you have shown me. Wow.

Thank you both. I hope this is the beginning of a long and lasting friendship."

BenJacnov
BenJacnov
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2 Comments
JgsexyJgsexyover 2 years ago

What a wonderful story of a boy being turned out. I wish this had been my introduction to anal. I’ve never experienced a threesome!

DevonCowboyDevonCowboyover 2 years ago

Nice! I could imagine myself as Jimmy as he was thoroughly taken by Lonnie & Toni

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