Jess Meets Her 1st Boyfriend

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Jess gets her first guy and Stepdad is there watching
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A series about a young woman & her exploration of sexual experiences. All characters are over 18 years.

Jess had called me, excited, to let me know that the Thunderbird football guy was coming over this evening. Could I please come over to the condo and meet him? I was to "just drop by" with the "stuff" Jess had wanted from the house. So I went to the Sex Shop and bought her a Wee Vibe four. with the remote control. And so she wouldn't be too embarrassed, I went into her bedroom and grabbed all the sexiest underwear I could find and threw that in the Holts bag on top of the Wee Vibe.

Jess was beside herself; this guy was only 27, in first year medicine, six foot four tall, blond, blue eyes, well built, and very handsome as well as Australian! It couldn't have been a better fit to her perfect man. I really hoped he was a decent guy. I'd find out soon enough. I stopped at the Liquor store and picked up four bottles of Molly Dooker (Aussie wine for an Aussie guy) and a bottle of Don Nacho tequila.

As I was about to ring the bell, the door flew open and I was face to face with Annie. She was dressed in a tiny bikini top and a pair of cut-off jeans that barely covered her crotch. As she turned to lead me into the living room, I got to enjoy the backside of her cut offs. There wasn't much there either; the cheeks were cut up nearly to the waist band in an artistic arch that started with the center seam of her former jeans and widened as it arched over the top portion of her exposed ass cheeks. It was obvious she wasn't wearing a bathing suit bottom underneath or a G-string for that matter (no place to hide it).

As my gaze returned to the room around me, I said "Hi" to Angus and Christopher (T-Bird Guy). Jess jumped up and ran over to hug me.

"Terry, this is Christopher, Christopher this is Terry. Christopher is the guy I was telling you about Terry. He plays football here at UBC. Christopher, Terry played professional football when he was your age."

Christopher nodded hos approval and came over to shake my hand. A well-mannered guy, this was very encouraging. He sat down beside me on the couch and proceeded to ask me all about my experience and where I played. We chatted for almost half an hour, and then I realized I had the "Goodies" for Jess and the wine! I motioned to Jess to come over and sit beside me.

I handed her the Holts bag and asked her to take the wine into the kitchen and open a bottle. As she turned to leave the room, I realized that Jess was wearing one of the shortest dresses I have ever seen her wear. From my position on the low sectional, I could see her ass cheeks and the bright blue band of her thong between her pink cheeks. If I could see that, so could Christopher! I then realized that Angus could also see her exposed ass too. He was staring and smiling as she left the room.

"The men" all acknowledged what they had just enjoyed watching and the conversation continued. Minutes later, Annie reappeared in different clothes. Now she had a very sheer pale blue silk dress that also barely covered her crotch. I could see her bright pink G-string under the dress and the matching sheer cupped bra. Her nipples were clearly visible through the bra and the dress; it was a very erotic sight! I looked at Angus and he smiled and leered at his girlfriend. It was obvious, by the tent in his jeans, which he was turned on by all the sexy outfits the girls were parading around in.

Annie sat down on the end of the sectional, her button front dress gaped wide apart, the buttons were only done up as far down as her belly button. Her tiny G-string was in plain view and she made no effort to keep her legs together. In fact, from Christopher's seat, you could probably see that her G-string was right up between her full fleshy lips. I couldn't wait to eat that meaty pussy!

Then Jess appeared with a tray of wine glasses and two opened bottles. She went around and poured everyone a glass, bending over deeply to hand us our glasses. Each time she bent over, her ass cheeks were in full view for those behind her. I noticed that she had removed her bright blue G-string!

When she finished serving, she sat down beside Christopher and started to talk to him quietly, it seemed rather intimate. I could tell she was turned on, her nipples were popping through the fabric of her dress (just realized the bra was gone too) and she was squeezing her thighs tightly and repeatedly. A sure sign she was pleasuring her clit. She had confessed that fact to me some time ago.

I started talking with Angus and Annie slipped down into his lap and reclined against the side of the couch. Her legs were over top of Angus' lap and her feet were now rested comfortably on my thigh. Annie's thighs were spread just far enough apart for me to be able to see her swollen shave pussy lips and her tiny G-string where it appeared at the top of her lips. It was a very erotic sight and it wasn't wasted on me!

I glanced over at Jess and Chris, they were laughing and really enjoying each other's company. I stood up and raised my glass. "I would like to propose a toast to the new roommates – Annie and Jess, may they enjoy many years together in this fabulous place!" We all raised our glasses and agreed on the toast.

"Now it's my turn to propose a toast. I would like to toast Terry. For introducing me to Jess and suggesting she come over and meet me and see if this place was right for her. Now, as a follow up to our first night together but including Chris, I would ask that those who desire, to join me in the hot tub for more wine, some tequila and some great conversation. Remember, it is a clothing optional tub. So Chris, if you want a suit, please tell me now."

We all turned to Chris, Chris turned red as did Jess, and we waited for his reply. The poor guy was on the spot for nearly ten seconds, but I'm sure it felt like an eternity to him.

Then Jess stood up directly in front of Chris and pulled her dress up over her head; she was now completely naked! "So Chris, can help you out of your clothes and do you want a pair of trunks?" With that, Jess leaned over and unbuckled his belt, pulled down his fly and then she straddled his lap as she started to undo the buttons on his shirt. From my vantage, I could see her pussy gaping apart; her nether lips were swollen with lust!

"No worries, don't need a suit if nobody minds me naked. I sure don't mind Jess naked on my lap or in the hot tub. So let's get naked and in the tub." Jess slipped off his lap and sat back to watch him take off his clothes. She was totally in heat and wanted Chris in the worst way!

Chris dropped his pants, pulled off his shirt and then slid down his boxer briefs. Jess actually gasped when she saw his long thick cock! It was a magnificent cock; it was already stiffening and well over nine inches long. Chris turned to Jess and offered his hand and helped her up to her feet. Jess' chest was flushed, her nipples were deep red and rock hard and she had left a small Jess Mess on the couch from her seeping pussy.

We all followed suit, so to speak, and stripped in the living room and headed upstairs to the roof top tub. There were seven seats in the tub and five of us to soak in it. I waited to see where the couples would settle and then slipped in between Annie and Chris. Jess was on the other side of Chris and nuzzling his neck as she caressed his bare chest. He was very well muscled, totally cut and very relaxed, considering the situation. Angus was beside Jess and had his hand on Annie's shoulder, slowly massaging her neck.

Annie sat back and slid down in the bubbling water and closed her eyes to enjoy the attentive hand on her neck.

Angus leaned in and looked at me, "She enjoys having both side rubbed at the same time. Feel free to rub wherever you desire to. She loves being touched anywhere, anytime." With that he moved his hand down over her breast and started to gently squeeze her nipple and then her full breast.

I took the cue and placed my hand on her other breast and started to roll her nipple and tug on it gently. Then I squeezed her full breast and cupped it from underneath and squeezed firmly, making Annie moan loud enough for Angus and myself to hear her. We both continued to massage her breasts causing Annie to start to moan a little louder. Then she spread her legs and placed them each onto our laps.

Annie wasn't shy! She reached over and gripped my cock at the same time she gripped Angus' cock! I took the cue to move my hand further down her body. I stroked her taught tummy and then I softly touched her nether lips. They were incredibly smooth and very firm. I slipped my finger between her lips and stroked her clit. It was fully erect and longer than I remembered it form the other night. I slowly stroked the length of the hard little shaft making Annie's hips buck against my strokes. Then Angus' hand bumped into mine. I looked at him and pulled my hand back, giving him access to her pussy lips and clit. I refocused on her breasts and then I leaned over and sucked her nipple between my teeth and bit gently on it. I figured it was Angus' job to pleasure his girlfriend so I sat back and watched the couples enjoy each other and their naked bodies.

Jess had also reclined back and was enjoying the hot bubbly water as she giggled and talked with Chris. I realized that Chris' hand was deep between Jess' parted thighs. Her eyes were shut; she was smiling and completely lost in sensual pleasure. Chris seemed to be a very attentive and skilled lover judging by Jess' actions, little noises and her shortness of breath.

Then Chris reached under Jess' arms and lifted her out onto the side of the hot tub and laid her back on a towel. Then he buried his face in her waiting pussy and licked her from rosebud to clit. Jess' hips were bucking against his tongue. Chris increased the tempo and focused on her clit; as her hips started to shudder, Chris thrust two long thick fingers into her gooey engorged pussy and went to work on her G-spot. Jess exploded in orgasm and her nectar shot like a hose all over Chris' face. Chris never missed a beat, he wiped his eyes and tasted her sweetness, and then he positioned himself between her parted thighs and drove his thick long cock deep into her heated depths. The whole 12 inches went in on the first thrust and Jess screamed out loudly as she rolled into another massive orgasm!

Jess pulled her legs back and wide apart, allowing that thick white pole full access to her deepest areas. Chris was a trooper, he fucked her through several more orgasms and then pulled his bare back cock out and shot his ropes of come all over Jess' heaving chest and neck! It was a very erotic sight for me to experience, first hand, my stepdaughter's first lover and first time having sex with a boyfriend. It was a fast first date, just like Stepdad's was, so long ago!

I looked over at Annie and Angus; they motioned me to join them. I slipped across the tub and they moved apart, so I sat between them. Annie leaned over and started to stroke my aching hard-on. I wanted to come badly!

"Need some relief Terry? How about stuffing that big thick cock either down my throat or up my ass. I love it in both places equally, so it's your choice because it's your turn for an orgasm. You are at least three or four behind us all!"

"I want your rosebud. I was staring at you in those shorts earlier tonight and wanting to rip them off and pound your tight ass!"

'My ass it is! It's actually my favorite too!" Annie stood up in the tub and turned around and thrust her perfect full ass out towards me and reached back and spread her cheeks wide apart. "Angus has already loosened up my rosebud, he had several fingers in me until I exploded in orgasmic bliss. I love having my ass fingered while stroking my clit. Now get that cock in me and make me beg you for more!"

I didn't need to hear any more words of encouragement; I moved in close behind her and gripped her full hips, once I had my beet red cock head nestled in her dilated rosebud. I barely had my hands on her hips and she pushed back against my cock and the head popped right in! I started out slowly and she was having nothing to do with that.

"Get your ass moving, and get that hot meat into my ass! I need it to hurt Terry, not like a schoolgirl!"

I obeyed and started to really pound her ass. She was grunting and pushing back as my cock impaled her completely. I realized why Kim Kardashian liked to have such a full high ass, it was to endure regular anal poundings from Kane! Nectar was oozing from her gaping pussy and I was ready to blow my load deep in her tight hot hole. I exploded, sending ropes of come into her. It felt so hot, with my fresh load of come and her tight glove like membrane wrapped around my throbbing cock. Annie's contractions were amazing, I felt like I was being milked like a cow. I slowly withdrew my softening cock from the grip of her full firm cheeks, what an incredible ass! It came out with a pop and my come gushed out of her wide-open ass and ran down her thighs into the hot tub.

"Better clean the skimmer tonight Angus." Annie said as she looked back between her parted thighs; my come was blobbing into the hot tub. "Terry pumped a gallon of come into me, he truly filled me up. It was the biggest explosion I've felt in my ass for a long time. Thanks Terry, you can tap my ass anytime you want, if that's okay with you Angus?"

"Fine by me, as long as I get to watch? And if it's cool with both of you, I'd like to eat that cream pie next time we do this?"

My mind went "bling" with an idea about fulfilling Jess' biggest fantasy. "Hey Angus, have you ever had a guy suck you off?"

"No, but I'd let you give it a go if you want to try it! Annie would really get off watching that!" Angus was looking really excited about the idea. I turned to see what Jess was doing; they had disappeared from the rooftop. I'd surprise her later.

"Come guys, let's go get a shower and have a nightcap." Annie headed to the stairs, not waiting for Angus and myself.

"Terry what's with the blow job question? You didn't come across as gay or even Bi for that matter."

"I'm just curious about what it feel like to have a thick hard cock in my mouth and throat. I know so many women who actually prefer to suck cock and swallow come than have intercourse. They say the feeling of the pulsing muscles in the shaft of a cock and the rubbery head pushing their limits of how far down their throat they can get a cock is a real turn on. One girl I enjoy regularly loves to lay on her back with her head hung over the side of the bed allowing her throat to open and align with her mouth. My cock can slide straight into her throat and I can fuck her really aggressively. I can get my full nine + inches in and feel her teeth bumping against my pubic bone. She gets so turned on that she has to have two big dildos stuffed in her pussy and ass with a pair of tight shorts over them, so when she comes they don't shoot out of her! The saliva flows out of her mouth like you left the tap on and she gags so hard her stomach cages up; all the while she moans like she's dying. She wants to know when I'm about to come, so she can start stroking her clit. Her fingers are almost a blur, they strum her hard nub so fast."

"I always enjoy telling her I'm coming just a little too soon. The sight of her orchestrating her own orgasm is amazing. Her body starts contorting, her stomach cages up until she looks pregnant, her legs are thrashing wildly, her fingers are a blur on her shuddering pussy and then her eyes roll back in her head as she explodes in orgasm. She really thrashes around but stays fully impaled on my cock. Spit is gushing out around my shaft, her cheeks puff right out and her face goes bright red. That's when I can't hold on any more and I start shooting my load deep into her throat."

"She makes the most amazing gulping noises, trying to swallow all my come, but usually it starts to gush from her mouth mixed with her saliva and flows around her nose covering her eyes and forehead. I've taken a couple of pictures of her face – post orgasm. She was actually shocked at what she looked like!

"No kidding, how do I get a shot at her? I'm rock hard, just listening to you!" Angus was wide eyed as he stroked his cock; pre-come was hanging from the tip.

"I'll see if I can get her to come over for a party one night, and I'll tell her to make sure she brings her twins and her booty shorts to play in. She'll know exactly what I mean. Oh, you should have seen those shorts once she was finally spent! They are absolutely soaking wet, there usually is a pool of her honey between her thighs. I always put a waterproof sex sheet on the bed before we perform this act. Then I turn her over, strip off the shorts. She lifts her ass up off the bed and I lick her clean. By the time I've got her cleaned up, my cock is rock hard again, her rosebud is right there and dilated about an inch and a half, so my cock slides right in and I pound her until she screams wildly. She's a really noisy anal girl, it's really wild!"

"Oh my god, I have to have that experience. I'm going to tell Annie about this girl, so she can be around when I get my chance at her. She's okay with multiple partners, isn't she?" Angus' eyes were wide and anxious.

"Absolutely, in the right situation, she would probably do every guy at a party and then ask the guys to go find some men that can satisfy her. She is as close to a nymphomaniac as I have ever seen."

"I'm going to go fuck Annie before she gets out of the shower, I'm too fucking horny now!" Angus headed downstairs to join Annie.

I sat down in a chair; naked as the day I was born and stared up at the stars. It was a perfect summer evening. Jess was going to be a perfect girlfriend and hopefully wife one day, an uninhibited woman will always keep her husband sexually fulfilled. It was going to be the perfect summer season too!

To be continued Chapter 7

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