Jess & Stepdad Look for a Boyfriend

This is chapter 5 in a series about a very horny girl and her stepdad, their adventures and orgasms!

All characters in this series are of legal age.

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Terry woke up slowly. He knew he was in his own bed, he knew that Tricia was out of town on business; so who was in bed beside him? Terry slowly rolled onto his back and looked over his shoulder to see who was beside him. It was Jess!

She was dead asleep, flat on her back, naked and barely covered. Terry decided he would wake her up like he enjoyed waking his wife up. Terry slowly crawled around to the end of the bed and then up between her wide spread legs.

Jess' tender petals were still quite puffy and a dark pink colour. They had enjoyed a lot of attention the previous night as well as on the ride home. Jess had passed out, reclined in her seat, knees wide apart, and no thong on; so Terry enjoyed fingering her meaty lips and strumming her engorged clit. Jess had come several times on the way home and never even woken up.

Back to the present! Terry slowly moved his mouth over Jess' pussy and then gently pressed his tongue onto her deep red clit. Jess moaned in her sleep, but she also spread her thighs further apart, instinctively! Her lips had now opened up and her sweet nectar was starting to bead at the bottom of her slit. Terry slowly circled her clit with his tongue, gradually pressing harder as he sped up the circular motion. Jess was still deep asleep but her hips were now thrusting against Terry's mouth and she started to moan in her throat.

Terry reached over to the nightstand and pulled out the G-spot vibe. Jess' pussy was now flowing with honey and Terry coated the vibe liberally and then started to tease her nipples. Jess' hips bucked quickly and her pussy gushed - she had already come! Terry continued to play with her nipples until they were deep red and rock hard. He coated them with Jess' nectar for a treat later.

Then he turned his attention to her gaping gooey pussy. He turned the vibe on low and slowly started to slide it into her creamy heated folds. Terry turned the curved tip so the point was now aimed at her G-spot and he started to run the vibe along her bumpy ridges very slowly. Jess was now thrusting her hips in time with the vibe. Terry turned up the intensity and leaned over and started to suck hard on her hard little nub! Then he started thrusting the vibe into her pussy, fucking her mercilessly as he sucked hard on her clit. Jess absolutely exploded in orgasm. She sprayed nectar all over Terry's neck and the sheets. She grabbed her legs and pulled them as far back as she could, giving Terry full access to her engorged wide-open pussy. Terry took the glistening pink vibe and slid into her rosebud and then grabbed the giant pink dildo and stuffed it into her pussy. Jess reached down and started to pound herself with the giant dildo.

Terry stood up and moved around to her head. He pulled her over the edge of the bed so her head dropped back down the side of the mattress. This opened up her throat perfectly and Terry lined up his throbbing nine inches of meat and started to slide it into her hungry mouth. Jess was gurgling and sputtering as Terry's cock slowly disappeared down her throat.

Terry grabbed her hair on either side of her face and started to fuck her throat. Jess started to cough, so Terry pulled his cock out.

"Don't stop, I love that feeling! I just coughed, that's all. Now get that monster into my mouth and fuck my face as hard as you want. I love the feeling of a thick cock being jammed into my throat." Jess never stopped pounding her pussy with the dildo as she talked to Terry.

Terry slowed down and just watched the show! Jess kept coming and coming and she never stopped pounding that dildo into her pussy. Terry reached over to the nightstand and grabbed another giant pink dildo.

He wanted to see how much cock Jess could take in her pussy. He moved around to the end of the bed and slowly started to push the second dildo into her slippery folds. Jess opened her eyes and looked down at Terry and just smiled.

"Go ahead stuff that into my pussy with the other one, I love the feeling of two big cocks in my pussy! As a matter of fact, I want you to arrange for a couple of really well hung guys to join you and I'll take all of you on. I want a gang bang Terry! I want every one of my holes stuffed with big cocks. I want two cocks in my pussy and I want to try two cocks in my ass too!"

Terry had the second dildo all the way into Jess' stretched pussy. Jess had her hands on both now and started to fuck herself with them, alternating them into her gooey hole. Terry grabbed her by the hips and pulled her to the edge of the bed. Her pussy was at the very edge, she had the two dildos deep in her pussy and then Terry moved in between her thighs and started to push his aching cock into her pussy too! Jess stopped pumping her pussy so Terry could get his thick cock in between the two dildos. Then he started to thrust; Jess held the two dildos in place and Terry was now getting all nine inches deep into her heated sex.

Jess was wild now, overcame with orgasmic bliss, her pussy just kept oozing nectar as she contracted on the three thick cocks in her pussy. Then Terry pulled out and dropped his cock done and thrust deep into her dilated rosebud! Jess' pussy shot a stream of nectar nearly two feet in the air!

"What the fuck! That was incredible! What did you do? Do it again!" Jess was sounding incoherent now, babbling absolute nonsense, as she lay there lost in orgasm after orgasm.

Terry kept pounding her now fully dilated ass. Her hole was at least two inches open. So Terry grabbed one of the dildos and then aligned it beside his hard cock and slowly pushed both of them into Jess' ass.

"Oh yeah, oh yeah, more, give me more. Give me all of it, pound me hard! I want you to fuck my ass until I scream." Terry was now really pounding her ass, his cock was throbbing, and orgasm was near! He wanted to come all over her breasts, so he grabbed the second dildo and stuffed it into her ass with the other dildo. He stood there at the end of the bed, slamming two fourteen inch long dildos all the way into Jess' stretched open ass. It was too much to watch and Terry exploded, his thick ropes of come flew all over her heaving breasts and stomach. After his orgasm had ebbed, Terry finished off Jess by slamming the two dildos into her ass until she gushed nectar again and begged him to stop.

Terry crawled up on the bed and started to lick his come off Jess' chest and stomach, saving her glazed nipples for last! Jess was already horny again and Terry slowly sucked her deep red nipples, one at a time. Making sucking and slurping noises as he moved from nipple to nipple. Then he licked down her tummy, cleaned out her belly button and was almost to her steamy, come covered pussy. The crown jewel, Terry thought as he lowered his mouth over her mound and licked the come and nectar from her meaty bump.

"That feel so good Terry, keep doing that please?" Terry obliged and then slowly started to lick her puffy lips clean too, avoiding her clit deliberately. It was deep red in color and the tip was almost white, her skin was stretched so tight with excitement. Her nub stood right up between her smooth bare lips, it was begging for some tongue time too!

"You know if I start on your clit, we will be here all morning!" I said as I hovered over her engorged little bud. "Make you a deal, if you let me lick your clit off, I'll only clean the come and nectar from it and not let you come." Jess groaned her displeasure!

"Hold on, I'll take you out shopping today for some new sex toys, some sexy clothing and we'll go see if we can find a well hung guy or two that we can have an evening with. Not tonight, but in the future. Deal?"

"You have a deal, now lick my clitty clean, it's really throbbing." I leaned over and started licking her hard little nub. I almost had all the come and nectar off of it when Jess came again! "Sorry, thanks to you I come really easily! Now let's get showered and go shopping."

They headed to the bathroom and jumped into the steamy glass enclosure. As Terry started to soap himself up, Jess dropped to her knees and inhaled Terry's semi-flaccid cock. He was hard in no time and grabbed Jess by the hair and pumped his thick cock into her mouth until he exploded. Jess stood up and kissed him deeply, his come flowed into his mouth and Terry swallowed.

"You like the taste of come?" I nodded. "Good, then that means I can watch you suck off a guy sometime, it's a real turn on for me and if you do it for me, I'll do absolutely anything you want me to, anywhere and any number of times. Yes, I will be your dirty little slut and pleasure you and anyone you ask me to, IF I can watch you suck off another guy!" Jess was rubbing her clit as she shared her desires with me. She came quickly!

"Okay, you have a deal Jess, I'll blow a guy while you watch. But remember, I will own you after that, for a full year! Do we still have a deal?" Jess just nodded as she flicked her clit to another orgasm. "Quit jerking off and get cleaned up. And wear something easy to change in and out of, like a loose dress please?"

"Okay, I know just the dress, not too slutty, not too conservative, just perfect! Do I have to wear panties and a bra?"

"Yes, and put on a pad, no Jess Mess today, okay?"

"Yes Terry. If I forget to do as you told me, will I get a spanking?" Jess just giggled and I watched her tight ass wiggle out of my bathroom and down the hall to her bedroom. I got dressed and headed down to the kitchen to wait for Jess.

She appeared in a few minutes, I was shocked! She had a little make-up on, her hair was in a ponytail and she looked radiant! The dress was pretty, knee length, buttoned all the way down the front and a floral silk print. As she passed in front of the window, I realized how sheer it was; I could see her panties and the style of trim they had on the waistband - scalloped and pink. Her bra was a pink lace-cupped bra and matched the panties perfectly! She had a pair of flats on and looked absolutely lovely.

"You look great!"

"You mean conservative?"

"No, you look radiant and very well put together. Now let's go!"

"Can we go to the Sex Shop last? I don't think I'll want to do anything else if we go there first. I'm so horny, just thinking of all the toys and ways to se them!"

"Good idea, let's go get you clothing, first some dresses and skirts, tops and jeans, then some sexy under garments like teddies, bras, thongs, G-strings, garter belts, stockings. I could go on and on. But I'm sure you want to buy a lot of this on your own?"

"Actually, this is way more fun, doing it with you. Mom is so conservative and never wants to spend too much. So spend away and I'll give you a great fashion show. Hey, we can ask Allie to model too!"

"I like that idea, I also like the idea of watching you two getting undressed and dressed. And I have a confession of my own; I like the idea of watching you with another woman."

"I like the idea of being with another woman too, make that several and throw in a few guys with big thick cocks and I'll just lay there and let them all have their way with me. Terry, Gang-Bangs really turn me on!

The fantasy of having endless cocks fucking me in every hole and women sitting on my face, until they come from my tongue and fingers and then they can clean the buckets of come off my sated body. It's making me really wet already! Have you and Mom ever been in an orgy or had other partners?"

" Never mind, let's get into the mall and get something productive done! I'll share some stories with you after you've finished shopping."

"Okay, Holt Renfrew first!" Jess beamed as she took my hand and led me towards Holt Renfrew's front door. This was going to be expensive! But this was going to give me years of pleasure and entertainment too. Between her and Allie, I had quite a pair of nubile young nymphomaniacs! Then I realized that Jess and I hadn't met Allie's boyfriend yet. I was hoping he was a really good looking guy, well hung, well versed, polite and properly sexually educated. I wanted to have a very good lover for Jess to train on, under over and with, when I wasn't around.

"Terry, we should call Allie. She's off today and she was planning on shopping too. Please, can we call her and have her join us?"

"Sure, give her a call." I watched as Jess excitedly called Allie.

They spoke for a few minutes and Jess was beaming, I knew Allie was going to join us.

"She on her way, and then we are going to meet her boyfriend and have lunch together, all four of us Terry."

"Great, let's get some intimates bought for you then, while we wait for her to meet us."

"Absolutely not, I want you to enjoy the two of us trying on intimates today! Let's go get some skirts and jeans now, please?" We headed into the junior coordinates area and Jess had ten pieces in less than five minutes and now she had to try them all on. I sent her off on her own, so she would get it done expediently. She picked three skirts and two pairs of jeans and a very elegant dress. Well done, it only set me back $1,245.78!

"Come on, Annie is waiting for us at Victoria's Secret, yummy, I can't wait to get into their stuff! Terry, will you promise to stay back near the change room where we'll be? So you can give us opinions on what fits, what looks good and what makes you really horny when you see us in it! That's the effect we're looking for." As we entered the store, we saw Annie standing over a huge table of thongs and G-strings (3 for $10). Jess started right in and found a number of pairs of bootie shorts in vivid colors and then she got matching G-strings for underneath.

Jess dug in and started to fill her basket with pair after pair of thongs and really tiny G-strings. Then they moved onto the next table, bras. Jess found a sexy shelf bra in hot pink that would have her nipples fully exposed on the underwire shelf as if she were braless. I told her to get a few colors.

Soon we were in the intimates; corsets, merry widows, garter belts, stockings of all sorts of patterns, crotch less panties (Annie grabbed four or five pairs of those!), masks, leather bustiers and even some latex panties and bras. Both girls had two full baskets now and we headed to the fitting room hallway in the back of the store.

They decided to share a room; we entered the room and there was an easy chair in the corner so I settled in for the show. I was rock hard in no time. Just watching those two strip off their street clothes got me aching; but now they were pulling on thongs and G-strings that weren't wider than a stick of Wrigley's chewing gum in the front and a simple string in the back.

They would walk over to my chair and sit on the arm, make me touch the fabric or lack there of it, and tell them if I liked it. Jess put on a black leather bustier than basically shelved her firm breasts and just (sort of) covered her erect nipples, a pair of black fishnet thigh high stockings, a black leather G-string and her electric pink pumps! What an outfit, perfect for a Lifestyle Event, which I said and preceded to explain them to the girls.

"You're taking us to the next one Terry, we'll be your slaves on leashes in outfits like this." Annie was stroking Jess' backside of the corset approvingly. The girls were really enjoying parading out in the aisle way where the other dads, husbands and women shoppers were in shock at the outfits they would go check in the mirror at the end of the hallway. It was better than the Victoria's Runway show, less clothing being worn here. They seemed in a hurry to finish shopping here.

"So why the rush girls?"

"Angus is meeting us for lunch in 45 minutes and we need to get a couple of really sexy dresses and our make-up done at Mac, before we meet." Made sense to me, LOL.

I settled that bill, $2,104.56 and we headed for a store they liked that sold rather risqué dresses for clubbing and parties. I left them there, with $500.00 cash and went to the washroom and then sat down and checked my email. The girls were going to buy a dress each, then go directly to Mac for make-up and meet me here in front of the restaurant. I figured an hour.

Well, I was wrong! They appeared in front of me 40 minutes later, looking ravishingly well dressed, if you were going to a nightclub!

Dress hems were less than 2 inches below their crotches, the plunging necklines just covered their nipples and their makeup was definitely "party hard till dawn". Kids these days.

We walked into the resaurant and asked if Angus had arrived, not yet, we were early! We picked a deep oval booth and I was asked to sit between the girls at the back. They informed me that they were buying lunch and Jess was driving home. Apparently I was going to get drunk now!

Annie whispered to the waitress ad she disappeared to get our drinks. We opened the menus and started to think about lunch.

"Annie, my sweet lassie, I finally found you!" We looked up and there was Annie's boyfriend - Angus. A true redheaded Scotsman built of solid rippling muscles and covered in freckles. He was definitely "A Hunk" as Jess would say.

I stood up and shook his meat hook of a hand and looked deeply into his bright blue eyes. He was a good man, I could tell already. Angus slipped in beside Annie just as a tray of drinks arrived.

There were four tall mixed fruit based drinks of some kind, eight shots of tequila (I think) and a basket of tortilla chips to get us started. "So what's this?" I asked, as I raised one of the hurricane glasses to my lips.

"Tequila Towers of Power, no grenadine in them, just three shots of Tequila, fresh lime juice and fresh orange juice; the breakfast of champions!" Angus responded. "Cheers lads and lassies, now down the hatch!" All three of them did down their drinks and then proceeded to shoot their two shots of Tequila after. I was slowly behind, but caught up fairly quickly, it was only 11:00 am, for god's sake!

Another tray arrived of the same. I looked at Jess and gave her the look of "no more, if you are driving". She smiled and passed on the drinks, instead now sipping her water happily. That didn't stop Annie and Angus; they finished everything on the table before the breakfast food had arrived.

Angus was a genuine guy's guy, but he was very respectful of Annie and gentlemen nonetheless, or so I thought!

"So Annie tells me you are hung like a horse Terry and you know how to use your Willie very well!"

I looked up at Annie, she smiled to say it's fine and that I could respond, "I've enjoyed the pleasures of a few beautiful women in my day, thanks! In fact Annie and Jess spent an evening in the hot tub with me exploring some deep throat diving techniques!" Everybody laughed at my poor joke.

"So when are we going to get naked and compare swords, and teach these lassies a few new tricks?" I love a good four way!"

"I was hoping we could find ourselves a suitable boyfriend for my Step-Daughter Jess."

"Oh yes, she's not your blood so she swallows your cock and come all the time, what a lucky man. To have such a beauty right down the hall when the Missus is busy or away."

"The Missus doesn't know Angus, and it's going to stay that way. That was why we are moving her in with Annie."

"Great, two naked nymphs to watch around the house when I'm there. You know Annie is seldom in clothes."

"Neither am I Angus," Jess piped up. "I also enjoy cock and Annie has approved me enjoying yours, given she has enjoyed Terry's - several times the other night. And don't I get some say in my first boyfriend and who he is?"

"Of course Jess, I'm just a little protective of you and I want the best for you since you are moving away from home." I smiled at her and she took my hand in hers and gave it an affectionate squeeze.