Jess Takes Stepdad Shopping

“Is she always this relaxed about nudity Sir?”

“Yes she is. She is actually my stepdaughter from my former marriage and she is very relaxed about nudity where ever she goes. I hope it doesn’t offend you in any way?” I replied. “I promised to buy her some new clothes today.”

“Not at all, she has a beautiful body, how would I be offended by looking at her? Besides, I think nudity is a healthy practice. I rarely have clothes on at home myself. How old is she? I’m looking for a roommate and I think we would get along really well. I have always worried about getting a roommate who turns out to be a prude!”

“She is almost twenty and entering University this fall. She is also looking at staying on campus here in Vancouver.” This could be a very interesting situation!

“Really, that’s where I rented a two bedroom apartment, actually condo, right on campus. I should give her my number and we could discuss the situation.”

“Agreed!” I responded as Jess stepped out of the change room in the first dress. It left little to the imagination; it was about two inches below her crotch and tight around her full firm breasts. It was evident she wasn’t wearing a bra too; the fabric was quite sheer.

“Jess it might be a little risqué for you, have a look in the mirror!” Jess turned and just smiled broadly.

“It’s exactly the look I want Terry. It’s for clubbing not for a dinner date!”

“Jess, I’m Annie and I think it looks really hot on you, if it’s for clubbing, it’s perfect. But I would wear boy shorts and a bra under it for protection!” Then Annie laughed with Jess at her comment, they both knew exactly what she meant!

“Right, that’s a smart idea, the boy shorts for sure. I’ll put the other one on now.” Jess started to drop the dress before she got into the change room and didn’t pull the curtain closed. Both Annie and I watched her change.

“Jess, Annie is looking for a roommate on campus for this fall at UBC.” With that Jess walked right out of the change room, still naked as she pulled the second tight spandex dress up her hips and torso.

“Really, Terry can I go see it, please?”

“Sure, when can we come out and visit you Annie and have a look at the place?” I asked.

“How is tomorrow night? I’m not working and we can have a glass of wine and talk about it, rules and expectations.”

“Great!” Jess said as she hugged Annie and then me. “Now how about this dress?”

“No, you look like a two bit hooker!” Annie replied. “Besides, if we are roommates I have a ton of dresses and we appear to be about the same size.”

“No, you have a much fuller backside than I do, but otherwise we are pretty similar. What size shoes do you wear?”

“I’m tiny, size five and a half.” Annie replied.

“Me too! Perfect then! We can share shoes too, if you are okay with that?”

“Works for me.” Annie was really comfortable to be around and Jess seemed to really like her. I hoped that the visit would be the beginning of something that would ease another worry of mine with Jess for university this fall.

We paid for the one dress and talked about what tomorrow night might bring, what Annie was like; Jess was the happiest I had seen her in a long time.

“Terry can we go buy some new lingerie now? I want to be wearing something really sexy tomorrow night and also something more grown up than cotton bikini briefs as well. It’s time I started to dress like a women. After all, I’m now a real woman and not a virgin anymore!” Jess smiled warmly at me as we strolled towards Victoria’s Secret.

As we entered the store, Jess grabbed a shopping basket and we started to look. In no time she had at least a dozen G-strings, several chemises, several pairs of shorts and three bra and G-string sets selected. We headed to the fitting rooms. Jess ran back out with one G-string in her hand two minutes later.

“Terry I have to have my own undies on to try on new G-strings or panties. So can you go pay for this one and bring it back to me please? I’ll try on the bras in the meantime.”

I headed to the cashier and paid, explaining the dilemma to a prudish old woman who should have been working in a grocery store not here. I returned to the fitting rooms and explained to the clerk and she handed the G-string in to Jess. An hour later we were done, Jess was well behaved and we headed home in the Rover. She was staring down at her newly acquired G-string, lost in thought.

“Thank you Terry, you were very generous today and I want to return the favor. Do you like Annie?”

“She seems nice, why?”

“Just wondering. Would you come with me tomorrow night to look at her apartment?” I nodded my agreement. “Do you think she is attractive?” I nodded my agreement again. “Would you fuck her?” I nodded again. “Would you let me join in?”

“Seriously, you want to have sex with your stepdad and another woman?”

“Yup, I want to see what being with a woman is like! I want to watch you make her come like you have made me come. Then I want you to watch the two of us make love. The idea of being watched while I am sexually engaged with someone is a total turn-on!” Jess was rubbing her clit now as she became lost in her lustful thoughts. Then I heard the buzz of her vibe start.

“Terry I’m coming! Annie’s body is so sexy. I can’t wait to see her naked. Do you think she likes women too?” Jess was bucking against her vibe as she shared her horny thoughts and I tried to focus on the road ahead.

“Don’t forget the towel Jess, no Jess mess on the seats please! I think Annie is a very sexual person and I bet she has enjoyed her share of women by the way she was enjoying staring at your body when you were changing dresses today. But just wait and see what unfolds tomorrow. Take it slow and easy; don’t push your horny thoughts on her. Okay?”

“Yes Terry. Can we please stop at the mall near home, there’s a pair of shoes I want to get for tomorrow night.” I nodded and watched Jess clean up out of the corner of my eye. The towel was well used!

We headed into the mall and found the shoe store. Jess picked out the shoes and sat down to wait for a sales clerk. I wandered around, looking for some other shoes in case the ones she desired didn’t fit or weren’t available in her size. The sales girl approached Jess and she handed her the she, telling her sizing. As the clerk disappeared into the back, Jess looked up at me and slowly parted her legs. Her G-string was right up between her puffy pink lips; her nether petals were fully exposed.

The clerk returned and sat down in front of Jess. As she took out the shoes and started to place on eon Jess’ foot she caught a glimpse of Jess’ exposed crotch. She nearly dropped the shoe and was obviously flustered! Jess leaned over, causing her knees to open more as she “helped” the clerk put on the shoe.

I kept my distance and pretended I didn’t see what was going on. The clerk was obviously captivated by what she could see between Jess’ thighs.

“Terry what do you think of these?” Jess called out to me across the store. The clerk just sat there staring at Jess’ crotch. I walked over and looked more closely and nodded my approval. “Great, I’ll take them.” Jess said as she sat back on the bench, leaving her thighs apart.

The clerk stammered, “Would you like to try anything else today?”

“No thanks, these are fine.” Jess said as she stood up and handed the clerk her old shoes to place in the box. “I’ll wear these out of the store.”

As we walked out of the store, Jess looked up at me and gave me a mischievous smile, “I like teasing girls too! I’m enjoying sharing myself with them as well as guys.”

“Just be very careful where you do it, you could get into some really tight situations if you tease the wrong guy or guys! You don’t want to get raped or gang-banged do you?”

Jess just looked at me with that same mischievous smile, “Maybe!”

“Be careful what you ask for Jess! Let’s go home and get dinner ready, it’s been quite a day! And tomorrow is going to be interesting, but you better behave if you do want to be Annie’s roommate.”

Jess smiled and winked at me, grabbed my hand and we walked out to the Rover.

To be continued!