Lucky StiffChapter 29 -- "Romantic" Date free porn video
Forward troubles Illinois,
Lock the front door, oh boy!
Look at all the happy creatures,
Dancing on the lawn!
Bother me tomorrow,
Today, I'll buy no sorrows.
Doo doo doo,
Lookin' out my back door.
--Lookin' Out My Back Door (Credence Clearwater Revival)
The next morning, I was sleeping in the spare bedroom with June. The two of us were in the "reverse spoon position" where June's breasts were pressed against my back. Through experience, we learned that this is a safe position because I was used to spooning against Kristen and waking up and fucking her. With June behind me, an accident could be avoided.
June also seemed to love this position. Throughout the night, I could feel June pull my body closer to hers and she'd rub her breasts against my back, her nipples hardening and feeling quite erotic to me.
It's amazing how lovely it is to just touch another person gently without having to stick your dick into a pussy or a mouth. Before I ever spent time with girls, I would have laughed if anybody had ever told me that I would be sexually satisfied with just snuggling with somebody warm and lovely.
I turned my head to look back at June. She was asleep, and June always looked cute when she slept. I kissed her right breast, rubbing my tongue around the nipple before sucking on it.
Without even looking, I could tell that June was now awake. After a few moments, I felt her hands lovingly holding my head to her chest as I continued to tease her breast with my tongue.
"You always seem fascinated by my body," June breathed.
I didn't answer, but I moved my head up until I was face to face with June. June and I kissed, our mouths opening to one another.
"Good morning, Baby," I said, smiling. "Baby" was a pet name that I recently started using for June.
"Good morning, Oogie," June answered with a giggle.
"Time for a shower?" I asked.
June looked at the alarm clock. "Oh! I have a doctor's appointment this morning!"
"You do?"
"Yeah. It's going to have to be a quick shower."
My face must have registered disappointment, but June gave me a kiss on the cheek as she got out of bed.
I watched the nude cheerleader hop into the bathroom.
About ten minutes later, June came out of the bathroom. She was wearing a robe and a towel around her head. She saw that I was still in bed, so she moved over to me, bent down, and kissed me again.
I pulled June down onto the bed.
"You're incorrigible!" June laughed as we playfully wrestled.
"You look good enough to eat!" I said.
"Not this morning, Oogie!" June laughed. "The doctor I'm going to is a gynecologist."
"You're saving my breakfast for him?" I asked, pretending to be shocked.
June, however, was shocked. "You nasty, nasty boy!" She laughed again after a moment, and then jumped out of the bed and opened a dresser and started to pick out outfits.
While June was dressing, I informed her that I "practiced" anal sex with Lynette, and that if still wanted me to take her ass, I'd be happy to take her out on a "date" first, to set the appropriate mood.
"Jim," June replied, "the last thing I think about anal sex is romance!"
"I want things to be different for you, Baby."
"I don't want romance, Oogie," June replied. "I want nasty."
"How nasty?" I asked June.
June was thoughtful a moment and said, "Surprise me!"
"Nasty?" I asked.
June closed her eyes and smiled. "Yeah."
"Really nasty?"
"Hmm," June breathed. "Sounds nice."
"Totally nasty?"
The way I kept on going further and further must have triggered some alarm within June's mind. "What do you mean, totally nasty?"
"How about in the middle of the mall? I hear that the back to school sales are starting up now."
June's eyes flew wide open. "Um, I think that might be a bit extreme..."
I smiled. "Just a bit?"
"If you want to take me in front of others, that's a turn on," June admitted. "I'd just prefer the others to be people who've seen me here at the apartment, and not necessarily the entire town."
"That sounds doable," I said. "I guess that would be really nasty, and not totally nasty."
June giggled. "Make it memorable."
Our date was for Thursday night. I told Kristen to take June to Martin's at the mall and pick out a wonderful gown that was sexy and lovely, but not out of place at a restaurant.
I told Kristen my plans, and she thought I was crazy. I explained that June agreed for me to take her in front of others, and Kristen just shook her head.
"I'll never understand the two of you," Kristen admitted.
"That's why I have June," I smiled softly. "I'd never do this with you, Kris. You'd never want it like June."
"If you asked me, Jim, I'd do it."
"The difference is that June asked me, Goddess."
"Can I be a part of it?" Kristen asked.
"How far do you want to participate, Kris?"
Kristen thought a few moments. "I don't need to see you... you know... in her ass. You do like making June feel a bit humiliated, and she seems to get off on that. Could I be a part of that?"
"Certainly, my fair Goddess!" I said, pulling Kristen into a big hug.
"You won't take my ass that way, will you, Jim?" Kristen asked.
I hugged Kristen once again and reassured her. "Of course not, Kristen. If you want your ass taken, I think it would be appropriate for your husband to do it the first time."
Kristen pulled away from me. "Husband?"
I smiled. "Didn't you ever want to save something for marriage, Goddess?"
Kristen hugged me very tightly and then gave me one of her erection special kisses.
Early Thursday evening, Kristen drove me to June's house. I got out of the Camaro, and Kristen drove off.
I knocked on the front door wearing the suit that Kristen got me at Christmas. Kristen picked out a shirt that she said would match June's gown, as well as a corsage.
Mrs. Rodgers answered the door, and was a bit surprised to see me there, like a kid on a date.
"Hello, Mrs. Rodgers," I said. "I'm here to go out on a date with your daughter. We're going to an Italian place out of town called Emilio's, and afterward, I plan to fuck her in the ass."
June's mother seemed a bit nervous when saw me at the door, but when I finished describing my intentions, her mouth hung open.
Undaunted, I said, "Please let me in."
Without saying a word, June's mother let me in. She once again had that "deer in the headlights" look on her face. I now felt that I had her mother correctly pegged as a bit of a submissive, and something within me seemed to naturally react to it.
"Oogie!" June bubbled when she saw me, dressed to kill. "Where are we going?"
"I have a gift certificate to Emilio's, Baby!" I said.
"Italian?"
"Yup."
June hugged me tightly.
"What time will June be home?" Mrs. Rodgers asked, trying to inject a bit of normality into this conversation.
"Well, I promised her an ass fuck, Mrs. Rodgers," I explained. "What if I promise to have her in bed by nine?"
June was shocked that I would say what I just did to her mother.
"Nine?" Mrs. Rodgers repeated, sounding quite uncertain of herself.
June looked from me to her mother and back. I gave June a big smile.
June's mother was staring at me. She looked as if she didn't know what to say.
Finally, June asked, "Mom, do you mind if I take the car?"
"Um... no..."
"Cool!"
We left a very confused mother behind us.
"You are so nasty, Oogie," June said as she drove us out of town. "Mom was so shocked, she couldn't say anything!"
I just smiled and dropped that subject. Instead, I made idle chitchat, since I wanted June to feel that she was truly on a date.
For our date, I was the perfect gentleman. Despite the fact that June drove, since I didn't have a license, I made it a point that the moment she parked, I jumped out of my side of the car and opened her door for her.
Kristen pulled out all the stops. As soon as we entered, the maitre d'hotel fawned over us. "Mr. Jim, Ms. June! It is so wonderful to have you here! We have a special table for you!"
June hadn't expected something like this, but she was definitely enjoying it. On the few occasions that June and I "dated" we drew more stares from people noticing the difference between our skin colors, and very little reaction like the respect that we were given at Emilio's (well, Vaughn's was an exception, as the manager there treated Kristen, our friends, and me like family).
At our table, we checked our menus. I already decided on a veal and mushroom dish that I liked, and wondered what June was interested in.
The waiter approached us. "Do you have a drink order?"
"A half-carafe of the house Chianti, please."
The waiter looked at me, and almost asked to see my identification when he decided that there were better things to do... like fetch our drinks.
"That's amazing," June said.
"Yeah. You ask for things, they bring them. It's how restaurants work."
June giggled. "Yeah. I'm glad things are working."
"I like how you blush, June," I said. "I can see a tinge of red in your skin."
"White people blush better," June said.
"Hey! You've got the blues, soul music, and you've got funk. We have blushing down to a science!"
June laughed out loud, holding her hand over her mouth.
"I'm sorry. That was a cheap joke," I said, seriously.
"I like the way you make our skin color difference almost meaningless," June said.
"The first time I laid eyes on you, during Sherry's initiation, I noticed you. I thought you were a cute person. The color of your skin didn't really enter into it. You tried to give me a French kiss to embarrass me, and I fought you back."
"You remember that?" June asked.
"Yup. There was a girl after you that grabbed my crotch, and my mouth opened, and after that, I allowed the rest of the girls to do whatever they wanted in my mouth. I remember being a bit disappointed that I hadn't gotten closer with you."
"My mom thinks you're dangerous," June said.
"If she thinks I'm dangerous, she'll learn levels of danger very soon."
June stared at me, and after a few moments said, "Sometimes, you're cruel to her."
"I didn't like being treated as a second class citizen in my own apartment, Baby," I explained. "Your mother has a right to prevent you from coming over, but she has no right to make demands of me in my own place. I reacted against that, and I think your mother and I both discovered something about her at that moment."
June shuddered. "I'm glad you're not angry with me, Jim."
"I'm not angry with your mom. Maybe I was that first time with her, but she deserved what she got. She seems to have always been interfering with your life, which I may resent, but I can understand. However, she thought she could bully me and interfere with my life, and she was mistaken."
The waiter arrived with a half carafe of wine and two glasses.
I poured a half glass for each of us.
June didn't know it at that moment, but Kristen was at the table right behind her. I promised that she could be a part of tonight to see the person I was with June, and I made sure that I treated June normally.
Well, I had plans. I was definitely going to take June's ass tonight. My relationship with June was on one level more romantic than it was with Lynette, but my relations to all of my paramours were based on their own attitudes. Kristen wanted to be my partner in crime tonight, although she didn't want to be around for the main event.
"Take your panties off, June," I instructed her.
"What?" June asked, surprised.
"You're wearing a dress. Take them off," I said.
June looked at me for a few moments, and then started wiggling a bit and after a minute, she said, "OK."
"Put them on the table," I said.
June's mouth opened, but nothing came out. After a few moments, she put her panties onto the table.
"Why did you do that?" I asked.
"You told me to do that."
"But you aren't any kind of slave--you're not that other persona any more. Why would you do something so embarrassing?"
June thought a moment, and then quickly took her panties off the table.
"You still have it, June," I said, very quietly. "If I were a different person, our relationship would be much different. You will have to tell Archy about this part of you if the two of you are to have a complete and loving relationship."
"You're scary," June said wistfully.
"I'm observant," I responded, raising my glass of wine. "I'm not really the guy that I pretend to be with you or your mother. Well maybe deep inside, I might be, but it's not a very big part of me. It feels more natural with your mother, because I can see she needs it more than you do."
June and I sipped our Chianti.
Neither one of us said much else and eventually our pasta arrived.
"That dress is really you, June," I said, complimenting her on her evening gown.
"Kristen has expensive tastes," June said. "I was surprised she bought this for me."
"It's a special occasion."
"Does Kristen know what we're doing?"
"Does it matter to you?" I asked. "She drove me to your house."
June shrugged. She still didn't have any idea what my plans were for tonight. She drank two glasses of Chianti, and I just had a couple of sips from my first and only glass.
The waiter arrived, and cleaned up our dishes. He took the empty carafe, but left June's mostly empty glass, and my nearly full one.
When the waiter came back, he asked, "Desserts, tonight?"
"Yes, please," I said, before June could answer.
The waiter handed us dessert menus.
"The chocolate mousse is fantastic here," I told June. "Kristen recommended it to me the first time I came here."
"I didn't know this place existed," June admitted. "It's a bit out of town."
"The first time I came here, Kristen and I were heading to Chicago for me to lose my virginity," I explained.
June's eyes widened. "Really?"
"Yeah," I said. "That's why this place is special."
"Ooh," June sighed.
When the waiter arrived, I asked for a chocolate mousse and two spoons for us to share.
"Anything to drink?"
"Tea for me. June?"
"Tea sounds nice."
The waiter nodded and left.
Neither of us spoke for the couple of minutes before the waiter reappeared with our mousse and our tea.
June took a tentative bite of the mousse and smiled. "This is heavenly!"
"Just like you, Baby," I said.
"Kristen and Lynette are so lucky," June said softly.
"Why?"
"Because they have you."
"You have me, too."
June's eyes got a bit moist. "It will end next summer."
"So, this is Paris," I said.
"Huh?"
"Did you ever see the movie Casablanca?" I asked.
"Humphrey Bogart?" June asked.
"Yeah."
"Yeah. It's a romantic movie."
"Remember at the end, when Bogey tells Ingrid Bergman, 'We'll always have Paris?'"
"Yeah," June said. "That whole scene makes me cry."
"We're in Paris right now, June."
"Huh?"
"I want to be able to walk you to the airline terminal that takes you to your college next year. I want to say, 'We'll always have your senior year.' I want you to live in the present as if each day is going to be more special than the next one."
"You're very romantic, Oogie."
"Thank you, Baby," I said. "A few minutes ago, you asked a question about Kristen."
"Yeah?"
"Turn around and ask her."
"Huh?" June turned around, and finally noticed Kristen sitting right behind her. "Kris! How long have you been here?"
Kristen smiled. "I got here about five minutes before you did."
Kristen then got up from her table, and took a seat between the two of us at our table.
"Have you heard everything we said?"
"Uh, huh."
"I'm so embarrassed!"
"Nothing to be embarrassed about. I sometimes get a little bit jealous about the way that Jim treats you all romantic, but it wasn't until I heard what you did with your panties that I realized that he was right. You are a different person than I am, and he treats you accordingly."
June blushed a bit. "Jim is so... dangerous."
"No, he's not," Kristen disagreed. "When he holds a mirror to your face and you see yourself for what you really are, that's not danger, unless you are truly afraid of yourself."
"Are you going to be around for... you know... ?"
Kristen smiled and shook her head. "No. I'm not really ready to watch something like that. I realize that Jim was telling me the truth. He told me what his plans are tonight, and he has my blessing, even if it's something that I'd never personally consider. If you want, you can tell me about how it went afterward. If you give Jim permission, he can tell me himself."
June looked at Kristen. "I find it difficult to believe that you could be jealous of me, Kris. I'm... I'm sometimes jealous of you."
"Don't be," I assured June before Kristen could answer. "You have Archy, and we have Paris."
"You really sounded like Bogey when you said that last part," June said, her eyes a bit watery.
"June, I think this is the beginning of a beautiful friendship!"
June and Kristen both laughed, and then June said, quietly, "Me, too."
Kristen left before we did, and I used my gift certificate to pay for our meals. I left a hefty tip, just as I saw Kristen do on countless occasions.
After Emilio's, I told June to drive me home. When she was about to head toward Kristen's place, I explained that I wanted to go to her house.
"My house?" June asked, making the correct turn anyway.
"I told you that I'd have you in bed by nine. It's nearly seven. A couple of hours early can't hurt."
"How will we get to Kristen's?"
"She'll pick me up tomorrow morning."
"You're spending the night at my house?" June asked, shocked.
"Of course," I answered. "I promised you an ass fuck."
"At my house?"
I didn't answer.
June sighed. "You are one fucking dangerous man."
Our arrival at June's house startled her mother. "Anything wrong?" she asked her daughter.
June didn't answer, but looked at me.
"I promised to have June in bed by nine."
"Did it hurt?" Mrs. Rodgers asked her daughter.
"We didn't do it... yet."
I pulled out a small wrapped box from my pocket and handed it to June's mother.
"What's this?"
"Open it. You get this if you strip naked right now."
June's mother laughed. "I'm not going to..." She interrupted herself, however, when she saw what was inside. It was a tube of KY Jelly.
"If you strip, I'll allow you to lube June up. Otherwise, her first anal penetration will probably be a bit painful."
Mrs. Rodgers and I locked eyes. There was no mercy in mine.
"I won't have you..."
I sighed. "Here we go again, Mrs. Rodgers. Whether you like it or not, June is going to get her ass fuck. We just went on a lovely date, and the last thing I need is for you to try to screw things up. Whether you strip or not, June's getting my cock in her ass tonight. If you forbid June and I to do it here, we'll either do it elsewhere, or I will take her on her eighteenth birthday in front of all her friends at her party. What would you prefer?"
June watched this whole scene in disbelief. She was even more shocked when her mother started to unbutton her blouse. I didn't watch. I simply told June to lead me to her room.
I positioned June so that she was on her stomach with her head near the foot of her bed. She was still fully clothed, although her panties were still removed--they were probably in her pocket book.
"Juicy June, you're going to get your wish tonight."
"I didn't think you'd include my Mom in this!"
"You said any of the others that saw you at my apartment. Your mother was one of them. Don't you see how alike the two of you are?" I asked.
June didn't answer.
Mrs. Rodgers entered June's room fully nude with the tube in her hand. "Do you want me to apply it?"
"Yes," I answered. "I don't think either of us want June's first time to be painful, so I think you would have incentive to do a proper job. I have never done this before."
"You've never fucked a girl in the ass before?"
"I have, actually," I admitted. "However, she applied the lube herself. I noticed that it wasn't very easy for her, so I just wanted to make sure that somebody would be there for June."
"You are so kind," Mrs. Rodgers said sarcastically.
Despite her attitude, June's mother did lube June's ass. I knew that at any time, she could have asked me to leave her house, but I truly believe that such a thought was the furthest thing from her mind, mostly due to the way our first confrontation turned out.
"That should do it," Mrs. Rodgers said.
"You sound as if you've done this before," I smirked.
June's mother simply glared at me and didn't answer me.
"I need you to do one more thing for me."
"What?"
"Grab your daughter's arms."
"Huh?"
"Don't ask, just do it!" I ordered.
Without a second thought, Mrs. Rodgers did as I asked.
"June, grab your mother's arms as well," I instructed her. "Don't let her go."
June did as I instructed.
I lifted the bottom of June's gown, and exposed her ass. I bent down and gave June's wet slit a noisy lick.
The next thing I did was to unzip the back of June's gown. The zipper went almost as far down as her ass, and when I got to my destination, I pulled the gown off her shoulders. Mrs. Rodgers and June had to let go of their hands in order for me to remove the gown from her arms, but they automatically grabbed each other again without being told by me when the garment was off.
Once June's arms were free, the gown easily came off. Luckily, June wasn't wearing a bra, so she was now lying naked on the bed, her arms still locked with her mother's.
Mrs. Rodgers glared at me, and hissed, "You are a bastard!"
I simply shrugged. "I never liked my real father, Mrs. Rodgers. Being a bastard would actually appeal to me." As I said this, I pulled off my clothes. I saw June's mom stealing glances at me.
"Is June ready?" I asked Mrs. Rodgers.
June's mother didn't answer, so I repeated the question, a bit more forcefully the second time.
"Yes!" Mrs. Rodgers said, her voice very stressful.
"June, make sure you have her arms tight," I said. "I want your mother to see your face. Look up at her."
June raised her face. The two locked eyes.
Slowly, I eased my cock toward June's pucker. She tensed, and her mother continued to hold her arms. The two women stared at each other, although I noticed the mother occasionally stealing glances at me.
I continued pressing, and eventually, June must have relaxed as I managed to slip a tiny bit further inside.
"Oh!" June said, surprised.
I didn't put much effort into the pushing, something that Camille told me over the phone would be the best thing for June's first time, but I didn't relax, either. I kept up a constant, albeit limited pressure. Once again, I felt June's hole open up a little as she relaxed some more.
Fawn
- 10.03.2020
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