Helping Jessica Get Pregnant

This is a story about an older couple helping a younger couple get pregnant. Just keep in mind that you don't always get what you want. Read on and enjoy.

I had taken my administrative assistant, Jessica, out to lunch for her annual review. Anyone who worked for me that long without quitting probably deserved it, and I had to admit I kind of liked Jessica. She was right out of college when I hired her, 23 at the time, and newly married. Although she could come off to some people as immature, she reminded me of a younger version of myself. I'm 35, and married to a great guy. But if I thought we would complete her review over a leisurely lunch, I was mistaken. This annual review session was turning out to be something else entirely.

"I just don't understand," she was saying as we sat eating our lunch. "Everyone I was close to in college got married, and they were pregnant their first year of marriage. But we just can't seem to conceive." She had only been married to her husband for a little more than a year, and had been trying to get pregnant since. They had been to get tested and the results indicated the problem was with her husband, Derek.

"Look Jessica" I told her, "There are plenty of options for someone in your situation. There are fertility clinics you can go to, artificial insemination – things like that."

"We can't afford any of that," she said. "Derek is still two years away from finishing law school, there's no way we can pay the money those places want. We will barely be able to afford the money we'll need for a newborn."

"Maybe we just weren't meant to have kids" she said dejectedly. "You and your husband are so lucky – you've already done it all and had children. I envy you."

I looked at her as she tipped back her wine glass to sip what was left out of it. I focused on the curve of her neck as it tapered down to her cleavage in her perfect little blouse, remembering when I had a body like hers. I thought about some of the conversations my husband and I had in our bedroom over the last six months.

"Actually" I told her, "There may be another way."

She looked at me quizzically as she lowered her wine glass. "Just what are you talking about?" she said.

"Look Jessica, you can still get inseminated naturally and it won't cost you anything" I told her. "Derek is the one with the issue, not you. It's just a matter of finding the right donor."

I gave her a minute to let what I was suggesting sink in.

"You mean, me with another man. Not with Derek..." she started.

"Yes" I stopped her. "That's what I mean. But it would have to be discrete, and with the right person. And I know the perfect man for it."

"Who?" she asked, now keenly interested, as she sat on the edge of her seat.

"My husband and I have the perfect setup. He's a doctor himself and has produced two lovely children. I was able to get pregnant as soon as we were married. I'm sure he could get you pregnant inside of a month or two."

I half expected her to reject my idea out of hand. But, her reaction surprised me. "Do you really think he'd do it?" she asked me.

*****

I was in bed with my husband, David, and I knew how to get his undivided attention. He was naked on his back and I was giving him a blowjob. "Yeah baby, that's it," he moaned as he stroked my hair, pushing my head down on his cock. "That's it, right there," he said as I started rubbing the base of his big cock with my hand.

"Hey honey," I said to him as I lifted my mouth from his cock. I knew he was frustrated from me stopping but I also knew I had his attention.

"Well, what is it?" he asked.

"Remember when we talked about having someone else join us? Like maybe another woman?" I asked him.

"How could I forget that conversation," he said. "I seem to remember you being almost as intrigued about the idea as I was."

He was right. I had confessed to him that I had always been curious about touching another woman. I mean, I didn't consider myself gay, at least I don't think so.

"Well," he said, "Tell me what you have in mind."

I placed both hands on his cock and began to ever so slowly stroke him. "Remember that young administrative assistant I hired about a year ago, Jessica. Well, she and her husband are having trouble getting pregnant."

"You mean that cute young thing that wears miniskirts to work? I'm listening." he said.

I continued. "Apparently they had a test done and it showed problems with her husband's sperm count. I suggested maybe trying to find a live donor."

"So you want to get that cute assistant of yours fucked by another man, not by her husband?" he said bluntly.

"Not just any other man. I told her I knew just the right guy to fuck her, someone who would be absolutely discrete. I could be there with her to make sure everything went just right...for her."

"And this other man. Just who did you have in mind?" he asked slyly, already suspecting the answer. His cock grew even larger anticipating the answer.

I went back down on him, taking as much of his cock in my mouth as I could. I felt his cock begin to convulse as he cum flowed upward. He shot stream after stream of hot jism into my mouth. I swallowed as much as I could but at least half dribbled down on my chin, neck and breasts. His cock bobbed and twitched as I stroked the last of his seed from him.

I looked up at him and said, "I didn't think you'd mind me offering your, ah, help," I told him.

*****

Jessica came into my office first thing Monday morning, closed the door and sat down in front of me. Her facial expression told me what she had on her mind...and it wasn't work-related.

"Did you talk to David about getting me pregnant?" she burst out. And then waited for me to answer.

"Yes," I said, "And its good news. David says, if its okay with both you and Derek, he'll do it. We both want to help you out."

"That's great," she said, giddily. "Although I have to admit Derek was a little weird about the idea at first. As I was."

I said to her, "Well, I guess I could understand you and Derek feeling that way, Jessica. It's a natural reaction. But, he should understand this is something that will make your relationship stronger. This is about you two starting a family together. It's all about you having a baby."

I could see our talk was making her feel better.

"Yeah, of course," she said. "You're right, I need to keep all that in mind."

I continued. "David and I have agreed to do this to help you out. Just think about holding a baby in your arms in nine months. Maybe it would be more comfortable for Derek if you came by just by yourself the first time, you know? And I'll be there to make you feel more comfortable."

"You're so nice to me," she said. "I don't know how I can ever repay you. So, when do you think we should try it first?"

*****

She came to our house on the Saturday night we had agreed to, by herself, nervous and visibly shaking. She and Derek had been to our house a few times before, but never for the reason she was here tonight. She was dressed in a simple blouse and a pair of jeans, which did nothing to hide her perfect young body. The fact that she was coming to our house to get fucked made the occasion so much more erotic.

I answered the door, "Jessica, come in!" I told her, and poured wine for the both of us. We went into living room, and sat on the couch to talk...and drink. I needed her to be as comfortable as possible before we started. After about ten minutes David came and sat with us and the three of us chatted. All the while I kept wine glass full.

Slowly, the alcohol had its effect. "Honey," I said, "Why don't you and I get ready for David?"

"Um, ok – sure" Jessica said. "What would you like me to do?"

"Well first," I said, "Let's go into the bedroom and get you undressed."

I had candles lit in our bedroom and had our lights turned on low, but still bright enough for us to see every part of her young body. I brought her into the bedroom, David followed but sat quietly in the corner while I prepared her.

"I guess I should take off my clothes," she said nervously. She began to unbutton her blouse but her hands were shaking so much she couldn't get the buttons undone.

"It's okay, honey," I said to her. "Here, let me help you." I had her stand up and my hands went to the back of her blouse and I gave it a tug to get it out of her jeans. I moved my hands around the bottom of her shirt, removing it completely from her pants. I could see her silky smooth skin between her pants and the shirt as I did it, and I was aware that my own body was starting to respond. I got the buttons undone and helped lift the shirt from her shoulders.

I felt a warm feeling deep inside me as I looked at her in her jeans and bra. I stood up and came close to her, our breasts touching, and reached behind her and unclasped her bra, letting it fall to the floor. "Go ahead and get your pants off honey," I told her; she nodded and her hands moved down to her zipper.

I became aware of the fact that my own nipples were hardening. I glanced at David in his chair and could see that he was shifting, indicating that his huge cock was probably stirring and starting to come to life. I looked back at Jessica and tried to focus on getting her naked.

She unzipped her jeans and then pulled them over her hips and down her slender legs in one of the most erotic moves I had ever witnessed. I couldn't wait to get her on her back with her legs spread for my husband. My excitement had gone past my nipples now – I could feel myself becoming wet.

"Ok honey, why don't you take your panties off and get on the bed," I told her. She nodded and slipped her slender fingers into her panty waistband. I was riveted as I watched her slide the panties down and reveal her trim little bush. She had a little bit of hair above her pussy and it occurred to me that she had probably trimmed up in preparation for this. I could just make it out since she was crossing her legs self-consciously. I realized she was blushing as she climbed up on the bed awaiting my next instruction.

I could feel my nipples hardening and pressing against my blouse. I thought about the conversation we had two weeks ago that had started it all as I unbuttoned the top button on my blouse and stepped towards the bed.

She scooted up on the bed and sat up on her knees. I knew this position wasn't going to work for what I had in mind. "Why don't you just lie down on your back, sweetie," I told her.

She nodded and laid back. I now had her completely naked on our bed. I climbed onto the side of the bed and went right for her body without giving her a chance to think about it.

"I just want to check that you're ready honey," I told her, and I put my hands on her pussy.

She started to pull away at first, gasping at my boldness. I opened up her thighs with my hands and started to explore her tender young pussy with my fingers. She was plenty moist - this whole process had gotten to her too.

"I think you are about ready, honey. David's cock is pretty large, so I just want to make sure you're ready for him," I told her.

My fingers went deeper in her pussy and I could feel her getting wetter as I worked her with my fingers. I turned to David and I nodded.

He never took his eyes off Jessica as he stood up and undressed. Jessica had her eyes forced shut, and I knew she was still struggling with the fact she was about to have sex with a man not her husband.

I motioned him to come on to the bed. She winced when she felt his weight on the bed and I started to speak to her again. "Shhh, just relax Jessica," I told her. "It's important to relax in order to let yourself get pregnant. Try not to be uptight or nervous, and just let your body react to whatever it's feeling."

She took a deep breath and exhaled, still keeping her eyes shut. "Okay," she said finally.

I propped each of her legs up so that they were bent at the knee and her feet were planted on the bed, and then I spread her knees apart from each other. The effect opened her pussy up wide to my husband as he moved toward her.

"Now I'm just going to spread you open and then David is going to enter you," I said.

"Uh huh," she said, "I hope it doesn't hurt".

"Relax," I told her again. "He's pretty big so you're going to need to be calm for him to enter you."

"Uh huh" she said again.

I kept my fingers spreading her as David put the tip of his big cock against her pussy. She jumped at his touch. I knew we had to continue before Jessica decided she wanted to stop. I nodded to David and he started pushing himself into her. I watched her pussy open up and yield to him as he pushed his big cock in. I saw her body go rigid as she tried to control herself but I knew what she was feeling. I remembered the first time I had let him put that thick cock into me and how I thought he might split me in half.

He had himself halfway in and she started to breath in half breaths.

"Oh my god!" she said. "It's so big. I've never had anyone this big inside me."

"Just relax honey. You need to be relaxed, I told her."

I stroked her hair to calm her as David continued pushing into her. When he got the entire thing in I watched her lower body start to shake. I got down close to her stretched pussy and watched him pull his thick cock out as he prepared to start going faster. She was panting now and I knew we had her right where we wanted her.

"Oh god," she moaned again as he started pushing it back it.

"That's it, honey," I said as I stroked her hair. "Just relax and let him fuck you with that big cock."

Her body twisted as he pushed into her the second time. I leaned forward and kissed her. She returned my kiss with her tongue pushing into my mouth. I think she wanted to say something to me and tried speaking but all that came out was an unintelligible moan.

"That's a good girl," I told her. "Just let your body relax and get pregnant honey. It's supposed to feel good, Jessica."

She gave me a half nod as she moaned. I tugged on her hard nipples and kissed her neck and lips, as my husband increased his pace on her. I could tell by the look on his face that he was enjoying this as much as I was. I stopped playing with her tits long enough to move down the bed towards his glistening cock.

He nodded at me and I knew that he was getting close. I was certain her young pussy was tight so I'm sure he was getting a cock massage much firmer that anything he had gotten from me recently. I reached down to her stretched pussy and I placed my fingers on her exposed clit. I knew he would be coming soon and I didn't want him to come before I could watch her have an orgasm.

I spread her pussy lips and starting massaging her clit with my fingers. Her arms shot out and she gripped the sheets with her hands as her orgasm started. I knew I had timed it perfect as I heard David grunt and saw his body start to twitch.

"That's it," I said to her as he stroked himself into her.

I wasn't sure she even heard me as her body arched and she moaned in pleasure. He stroked her three, four, and five more times before he had expended all his cum inside her. His body slumped and he pulled himself out.

Jessica's body was spent and she didn't move, almost semi-conscious. David and I rubbed her body all over until she recovered. We were concerned that she might be to worn out to drive so we took her home, she and I in our car and David driving her car.

*****

It was six weeks later. Jessica and I were again talking in my office. "I just don't get it – I thought we did everything right." she said. I was listening to Jessica lament her latest pregnancy test. She had gotten the big negative and she was devastated. I had warned her not to get her hopes up. I had told her it had taken David and I at least two months the first time I had gotten pregnant.

"It doesn't always happen right away honey," I told her. "Plus you were nervous the first time with David. I know that will make a big difference."

"I know, I know – I shouldn't have expected it to happen the first time," she said. "It's just so frustrating. Plus I just heard from a friend of mine on Facebook that she's pregnant, and it's not fair, and..."

She was blabbing on and on about her pregnant friend and how life was unfair, and I had stopped listening to her five minutes before. It wasn't that I didn't want her to get pregnant – I would have loved if the little test showed a plus sign for her. It wasn't that at all. I was thinking about how fantastic my sex life had been since I brought Jessica into our bed.

David and I had been fucking like rabbits since I let him fuck her. It was a natural fantasy for an older guy like him to stick his dick in something new, I had known that. What I wasn't prepared for was how hot it had gotten me. I had thought about little else since having Jessica's tits in my hands. I had loved playing with her pussy. I had loved taking off that lace bra of hers and playing with her nipples. I loved getting her off. She didn't know it but my pussy was getting wet just sitting there thinking about it.

On and on she droned. "And then there's Barbara. She's already on her second husband and she's having her third baby. I mean come on..."

I realized that her disappointment now meant that I would have another shot at her if I wanted it. And I was pretty sure I wanted it.

"I don't know," she said. "Maybe it just isn't meant to be."

"Don't talk like that," I told her. "You can't give up that easy. You have to at least give it another try."

"I don't know," she said. "Derek was kind of weird about it last time. I don't think he wants me to come over there by myself again."

"Then it's settled," I told her. "Tell him to come with you next time. Now let's have a look at your lady calendar to figure out the best time for the two of you to come by."

*****

Derek and Jessica arrived together the next Saturday as planned. I knew that Derek would be the nervous one this time. I had dressed in a blouse with the first three buttons unbuttoned, no bra, and a short skirt that David particularly liked. I figured I would do anything I could to distract Derek and win him over.

He was noticeably reserved when they came into our house, but it was something I had prepared for. I made sure the wine flowed early and often as the four of us sat down to talk to one another.

Jessica was definitely more at ease with us this time and drank freely. Derek took a little longer to warm up but I made sure to bend over in front of him several times to refill his glass and I could feel his eyes on me. I let an hour go by and had judged that everyone was significantly relaxed when I started to lead Jessica to the bedroom.

"Derek, are you sure you're okay with this?" I asked him. "Are we ready to get started?"

"You just need to understand," he said, "I feel a little uncomfortable with someone else fucking my wife."

"Honey I understand," I said and I wrapped my arms around him to give him a hug. I made sure to press my breasts into his chest to punctuate my point. "That's why I think you should be involved too. It doesn't need to be awkward. We both want you two to have a baby."

I took Derek by the hand and led him into the bedroom, with David and Jessica close behind us. "You should undress her, Derek" I said, and David and I stepped back.

I was half expecting he might take her and leave the house right then. But between my suggestive argument and the wine he had softened. He went to his young wife and started to unbuckle her pants. David and I stood and watched as he pulled down her zipper and then had her sit on the bed. He removed her shoes and then tugged on her jeans as she wiggled her cute little ass and the jeans slid off her body. She still had all of her clothes on her upper body as she scooted her butt back up onto our bed.