Long Time, No Suck Ch. 04

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Time marches on and stuff gets interesting.
2.9k words
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Part 4 of the 4 part series

Updated 09/22/2022
Created 08/26/2014
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That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence.

Marc had to go back to town on business for several days, but Stephanie said he knew all about this, so when I entered her condo and found them (Steph and Cloe) making out, it wasn't a shock. Cloe looked very seductive in barely there red lingerie.

She was looking into me, as she boldly called me over in an authentically female voice, never letting on to the big surprise I was soon to find. Stephanie kissed me, then seemingly passed me to a very amorous Cloe. Stephanie guided our heads together, our lips meeting, as Cloe soon forced her tongue into my submissive mouth. She then placed my hands on her near perfect tits, easily a 36 C, that felt so real. I was drawn into her Baby Doll perfume.

Cloe sat on my lap with her arms around my neck, Stephanie appearing to me like a cat that had eaten the canary. She stood up and began kissing Cloe, as Cloe remained on my lap.

At some point I realized that Stephanie was giving Cloe a hand job, when I hadn't known that Cloe even had a penis. My own member had been hard since Cloe had sat down.

I made eye contact with Stephanie. I knew what my Goddess wanted. Without hesitation, I leaned forward and licked the big shemale cock head. Cloe pushed my head forward, as Stephanie bit her lip. She knew what her lover was capable of, and part of her continued to have strong feelings for me.

Stephanie audibly gasped, as Cloe forced me to swallow more of Clarence into my mouth,

Cloe:

Come on Tommy, swallow Clarence down, ooow, Stephanie was right, you do have cock sucker lips. They're my cock sucker lips, that's it, use your tongue, mmmm

Stephanie can fuck you whenever she wants

and if you ever want to fuck me, I'm all yours

Cloe then pulled me up to kiss m, when I pulled back for a moment

Me:

So you don't want to fuck me?

Cloe:

No, are you disappointed, I mean, you do have a cute ass, hhmmmm, no, but Stephanie tells me you know how to hit the spot.

As Cloe said this she rolled towards me, our cocks rubbing through the fabric of my Dockers. Cloe's nothing dress was gone, her perfectly fake tits were out, as were Stephanie's. She approached, grabbed my head and forced me back to work, pleasuring her partner, Cloe.

Stephanie:

That's it Tommy, suck that big cock, make it cum for me. You love cum, don't you, Tommy?

Me:

mmmhmmmm

Stephanie:

Make Cloe cum for me Tommy, and I'll fuck your naughty ass

Surprisingly, hearing that combined with my blowjob set off Cloe's fuse, I could feel her thick shaft throb in my hand, as more sweet precum hit my tongue. Both of my hands instinctively began playing with her balls. Sinking my thumb deep into her ass finally set her off, I couldn't swallow it all, and I tried.

Stephanie began kissing me, right after Cloe thanked me with a sweet kiss, then left. Stephanie sat on my lap. My hard on pushing up between her ass cheeks as her wet pussy settled down on me. We'd always had a special something, but this was even more than when we were younger.

Stephanie:

Tommy, I love that you're my slave. Let's go for a drive.

Me:

Okay, Goddess

She stood up and grabbed my cock

Stephanie

I have plans for this

We spent the afternoon making out like we did in the back of my parents' musty basement, on that old couch, only now we were on a $5000 rosewood framed bed with a pillow top mattress. We played, but Stephanie never let me cum. I could tell that she was up to something, or maybe she continued to execute some mischievous plan. My past experience with her suggested the latter.

Stephanie:

Time for a supply run, Slave. If I tell you to do something, just do it, UNDERSTAND?!?!?

Me:

Yes, Goddess

My cock was raging, I was turned on with fear and anticipation of what she obviously had planned for us. We loaded into the pristine old Plymouth for coffee, then the local grocer for meat, some expensive organic veggies, then the promise of Amish cheese

As we pulled into Fastgas it was coming on dusk as Autumn set in hard. A devilish smile befell Stephanie's perfectly pampered face as we entered the convenience store for some coffee. There were two clerks on, a muscular guy and a cute girl, who both looked to be college aged.

Stephanie introduced me to Rich and Chelsea. Both of them were Juniors in college Chelsea seemed to be plugged into her cellphone, while Rich appeared to be quite friendly. When we shook hands, combined with momentary eye contact my now slumbering cock jumped. I had to be mistaken. Surely, a young guy with ice blue eyes, a fullback's body, and the charm of country living, has girls coming and going. Our hand shake lingered, but Stephanie pulled me away.

Stephanie:

Thomas, leave that guy alone, now come in the back, we need to get beer.

She grabbed my hand and we headed towards the back.

Stephanie:

It's not here, hmmmm, maybe it's in the walk in.

As we made our way into the cooler, we were eventually joined by Rich, as Stephanie had planned in her wink to him that I missed as we entered. As it was now Sunday, she'd had time to plot a plan. Unknown to me, Rich was a confirmed bisexual, as well. It had seemed that the present generation is much more comfortable sexually, than we were 15 years ago. Rich followed us, a few moments later, into the back of the large walk in. Before he came in Stephanie stopped and whispered in my ear

Stephanie:

Tommy, I want you to flirt with Rich. Compliment his arms, he loves that. He told me he was straight, but my gaydar goes off whenever I see him, and the look he gave you, he was hard when you shook hands with you.

Me:

He was not. Really? He couldn't be into guys, not a guy like him, girls must love him. I'll bet he's even a football player, like I was,,,,

Stephani:

Exactly

She barely spoke that word when Rich's smiling blue eyes entered the dimly lit cooler. As per my Goddess's orders I began to flirt with Rich immediately. As he entered, I gently squeezed his bulging left bicep as I stared into his eyes

Me:

Rich, I normally don't notice another guy's eyes, but yours are absolutely stunning

Rich actually blushed as he bowed his smiling face

Rich:

Thanks, Thomas, I think you're pretty good looking, too

An audible gasp left Stephanie's mouth as Rich leaned forward to kiss me. It was welcomed by my again rock hard cock. Seeing us kiss, Stephanie again whispered something in my ear.

Stephanie:

Drop to your knees and suck his dick, right now

I pulled away from Rich, who by now had been stroking my ready to explode cock, as I was his, through our pants. If what I felt through his jeans was any indication, I was just hoping Rich wasn't a top. As I pulled away, I hushed Rich with a finger to my lips, then dropped down to my knees quickly, as to not get caught. Unleashing his beast was a nice surprise. He was commando and wasn't as thick as I'd feared. As I swallowed his cock head into my mouth, the sweet taste of copious amounts of precum made me even harder.I bobbed my head and stroked his shaft. Stephanie joined me, and we soon had him filling my mouth with his cream, which I shared with Stephanie, who finally got a kiss from Rich.

How we didn't get caught, still amazes me. Rich slipped his number into my hand as he hurried back to work. Stephanie and I grabbed a case of beer and a twelve pack of hard cider . As we left Rich winked at me, as Stephanie giggled and grabbed my crotch. I was just happy to have some fun and I'd grown to truly enjoy pleasuring men.

I called Rich as we pulled out and thanked him for his special attention. He apparently wanted someone to think I was a woman, so I put him on speaker and played along to Stephanie's amusement

Rich:

Oh Baby doll, your lips felt incredible, I can't wait to bang your sweet ass

Me:

(whispered)I'll play along (in my best sexy lady voice) Oh yeah, big Boy, I want to feel your big cock cum deep inside my naughty ass

At that point I heard him gasp, then I lost his connection. Stephanie and I laughed as we entered the upscale, strip mall parking lot. We stopped to enjoy our Fastgas latte's and a bowl of kush.

Stephanie:

Tommy, I had no idea that you could imitate a woman so well, you were so girly. That was amazing, does she have a name?

Me:

Does who have a name?

Stephanie:

The girl you have trapped inside your cute, sexy, and very interesting ass

Me:

Oh, that voice is just something I can do. ha, ha You really think I sound like an actual woman?

For some reason, the thought that I sounded like a woman was turning me on. I enjoy being a man, and I have no intentions of ever cross-dressing, but the idea that the feminine side of me had crept out, made sense. And it was obviously having as surprising affect on Stephanie in the moments before we lustily embraced.

Stephanie:

Yes, Tommy, you do, and watching you suck that young guys dick like that, mmmhmmm, feel how wet I am, Thomas (she buried my happy digits into her honey pot, which seemed to suck them in, as she began to smile) I think I'll call her, Jamie. Oh, and you have to let me buy you something today, mmmmmmpanties

The windows were steamed before we began to make out. I soon had Stephanie trembling uncontrollably, cumming hard as we kissed, and was there something about panties as she came?

We straightened up, smoked up, then hit the stores for supplies. After the grocer, Stephanie took over

Stephanie:

Tommy, be a Doll and help me pick out some new panties to surprise Cloe with, I want to get them matching.

Me:

Really, you think that you have to ask me if I want to watch you try on sexy outfits? Hello (pointing to the outline of my now hard cock inside my jeans), ha ha, I'm in

Stephanie:

Awww, thank you, Tommy, you are one sexy beast

We went into the changing room after Stephanie had selected several very sexy panty and bra sets that I happily approved of. Stephanie brought me into the spacious changing room with her, then handed me her choices.

Stephanie:

Here Tommy, try these on

Me:

Excuse me? I am not going to try on panties

Stephanie:

Yes, you are, because you told me you would do whatever I told you to do

Without another word, I kissed her lightly, then obediently tried on the silky soft panties. The feeling of my cock surrounded by the silky material was amazing, my cock felt harder than it had ever been and I began to copiously gush pre-cum.

Stephanie:

My, oh my, Jamie, doesn't your ass look pretty, he he

Me:

They do feel great, and it makes sense, my ass has been more of a pussy lately. I bet Marc will enjoy them

Stephanie:

Marc, what about your new boy-toy, Rich

Me:

Rich? He's fun, but he's barely out of high school. I bet he'd cum if he saw me now.

Stephanie:

I want you to think about pleasing, Rich. Marc knows all about this. Call Rich and offer him a ride home. Call Rich but be, Jamie

Without thinking, I had my cell out and hit redial, then spoke as Jamie

Me:

Rich,this is Jamie. I had so much fun with you and Stephanie earlier, that I was wondering if you wanted to cum play with us some more. When do you get off?

Rich:

As soon as you can pick me up, Jamie-baby we close in 10 minutes

Me:

See you soon, Stud

Stephanie drove, as I jumped into the backseat, soon we pulled into the dimly lit Fastgas lot, Rich, smiling from ear to ear, awaited my arrival. He jumped into the backseat and we headed back towards Marc's condo. We never made it there though.

Stephanie smiled back at me in the rear-view and said,

Stephanie:

Rich hon, do you know about the old Johnson cabin, out on Pine Bluff?

Rich:

Sure, but they're in Florida until next May

Stephanie:

I was hoping you were going to say that. Now Rich hon, open your present

Rich:

My present? Where is it?

I knew exactly what my evil friend was up to, and I raised my finger to Rich's lips, then pointed my finger toward my throbbing bulge, as I unzipped his present.

Stephanie:

Rich hon, this is, Jamie, whenever Thomas is wearing panties, that's her name, and I want you to treat him like you would normally treat your real girl friends, okay?

With that, Rich suddenly, and roughly, pushed me against the big backseat, forcefully french kissing me, as his beautiful cock venomously glided over my silky imprisonment. He began humping my pantied cock, leaving no questions as to what lie before us.

Stephanie suddenly interrupted us, as Rich released, then swallowed my throbbing cock from the panties she'd picked out

Stephanie:

Jamie, you look so hot together with your new boyfriend. I bet your pussy is dripping

I could only bite my lip as Rich bobbed up and down, completely deep-throating my cock, and as Jamie, I went totally submissive, wanting to pleasure Rich for Stephanie. We pulled apart, redressed and entered the old, sparsely furnished cabin. They did have a couch, a big recliner and a fireplace, with a large loft bedroom, with the bed cushion filling the loft.

After starting a fire, opening some beers and settling in for a smoke, Rich suddenly remembered his place

Rich:

Jamie, come over here and suck my cock in front of Stephanie. She looks like she wants to watch you pleasure me

I stood, then slowly undressed

Jamie(me doing the girl voice seductively)

Yes, Baby, but wouldn't you rather fuck me,(ass wiggle) instead?

Rich:

You heard me, Jamie, get over here and suck my cock!!

Obediently I dropped to my knees in front of Rich sprawled out on the over sized couch, then I decided to do something different. I began seductively giving his throbbing monster a panty clad lap dance. Stephanie responded with an MP3 of Pour Some Sugar on It. I rubbed my silky panties all over him, sitting on his lap and kissing him, as his throbbing hard, naked cock jumped and begged to be pleasured. I grabbed, stroked, fondled and played with his shaft and balls, occasionally swallowing his precum dripping head into my mouth

Stephanie:

Jamie, you want Rich to fuck your pussy, don't you

Jamie:

That might be fun, sure

Rich:

What are you waiting for, Jamie, take off your panties and show us your pussy, and your big clitty

I dropped the panties to the floor, standing there naked, turning round for their inspection. Stopping with my ass to them per request, I could feel Stephanie's manicured, lubed up fingers sliding deep inside of my ass, which were soon replaced by Rich's less experienced, much thicker fingers. As Stephanie began kissing Rich, his fingers found their rhythm, and soon I was again begging him

Jamie:

Please fuck my pussy, Rich. I want to feel your big, hard cock,,,

With that, Rich positioned my ass on the edge of the couch, brought his monster up for a final lick from Stephanie and I, then slowly and painfully, but forcefully, he began to fuck me. He was treating me the way I treated women when I was his age and it felt great to feel like I was his to do with as he wanted.

I could feel his pubes finally tickling my ass cheeks and he started to pump in and out. I just tried to relax into it. My cock was rock hard, as I watched Rich's face signally me, combined with his suddenly throbbing cock that he was about to cum.

Rich erupted, dumping his hot load deep inside of my ass. Stephanie leaned in for my own orgasm as I started to shoot. I hated to admit it, but he was an even better lover than Marc. We all ended up cramped inside the barely heated shower. My panties off, I returned to being Thomas.

Me

Rich, get over here and suck my cock

Rich

Yes, Sir

Me:

Stephanie, get over here and help him

Stephanie:

Yes, (wink) Sir

That evening turned into us back at the condo, where Marc returned early and threw me out for cheating with Rich. "Thanks, Steph", so I headed back to the city and my job. Rich found me with the help of Stephanie after a few weeks, but I'll save that for next time.

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